Structural insights and cytotoxicity evaluation of benz[e]indole pyrazolyl-substituted amides

Five new compounds of benz[ e ]indole pyrazolyl-substituted amides ( 2a–e ) were synthesised in low to good yields via the direct amide-coupling reaction between a pyrazolyl derivative containing a carboxylic acid and several amine substrates. The molecular structures were determined by various spec...

Full description

Saved in:

Bibliographic Details
Published in	Molecular diversity Vol. 28; no. 3; pp. 1363 - 1376
Main Authors	Ramle, Abdul Qaiyum, Chan, Nadia Nabihah Mohd Yusof, Ng, Min Phin, Tan, Chun Hoe, Sim, Kae Shin, Tiekink, Edward R. T., Fei, Chee Chin
Format	Journal Article
Language	English
Published	Cham Springer International Publishing 01.06.2024 Springer Nature B.V
Subjects	Amides - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biochemistry Biomedical and Life Sciences Cell Line, Tumor Cell Survival - drug effects Crystallography, X-Ray HCT116 Cells Humans Indoles - chemistry Indoles - pharmacology Life Sciences Models, Molecular Molecular Docking Simulation Molecular Structure Organic Chemistry Original Article Pharmacy Polymer Sciences Pyrazoles - chemistry Pyrazoles - pharmacology Structure-Activity Relationship Toxicity X-ray crystallography Cytotoxicity DFT Minor groove binding
Online Access	Get full text

Cover

Loading…

Abstract	Five new compounds of benz[ e ]indole pyrazolyl-substituted amides ( 2a–e ) were synthesised in low to good yields via the direct amide-coupling reaction between a pyrazolyl derivative containing a carboxylic acid and several amine substrates. The molecular structures were determined by various spectroscopic methods, such as NMR ( 1 H, 13 C and 19 F), FT-IR and high-resolution mass spectrometry (HRMS). X-ray crystallographic analysis on the 4-fluorobenzyl derivative ( 2d ) reveals the amide- O atom to reside to the opposite side of the molecule to the pyrazolyl- N and pyrrolyl- N atoms; in the molecular packing, helical chains feature amide-N‒H⋯N(pyrrolyl) hydrogen bonds. Density-functional theory (DFT) at the geometry-optimisation B3LYP/6-31G(d) level on the full series shows general agreement with the experimental structures. While the LUMO in each case is spread over the benz[ e ]indole pyrazolyl moiety, the HOMO spreads over the halogenated benzo-substituted amide moieties or is localised near the benz[ e ]indole pyrazolyl moieties. The MTT assay showed that 2e , exhibited the highest toxicity against a human colorectal carcinoma (HCT 116 cell line) without appreciable toxicity towards the normal human colon fibroblast (CCD-18Co cell line). Based on molecular docking calculations, the probable cytotoxic mechanism of 2e is through the DNA minor groove binding. Graphical abstract
AbstractList	Five new compounds of benz[e]indole pyrazolyl-substituted amides (2a-e) were synthesised in low to good yields via the direct amide-coupling reaction between a pyrazolyl derivative containing a carboxylic acid and several amine substrates. The molecular structures were determined by various spectroscopic methods, such as NMR ( H, C and F), FT-IR and high-resolution mass spectrometry (HRMS). X-ray crystallographic analysis on the 4-fluorobenzyl derivative (2d) reveals the amide-O atom to reside to the opposite side of the molecule to the pyrazolyl-N and pyrrolyl-N atoms; in the molecular packing, helical chains feature amide-N‒H⋯N(pyrrolyl) hydrogen bonds. Density-functional theory (DFT) at the geometry-optimisation B3LYP/6-31G(d) level on the full series shows general agreement with the experimental structures. While the LUMO in each case is spread over the benz[e]indole pyrazolyl moiety, the HOMO spreads over the halogenated benzo-substituted amide moieties or is localised near the benz[e]indole pyrazolyl moieties. The MTT assay showed that 2e, exhibited the highest toxicity against a human colorectal carcinoma (HCT 116 cell line) without appreciable toxicity towards the normal human colon fibroblast (CCD-18Co cell line). Based on molecular docking calculations, the probable cytotoxic mechanism of 2e is through the DNA minor groove binding. Five new compounds of benz[e]indole pyrazolyl-substituted amides (2a–e) were synthesised in low to good yields via the direct amide-coupling reaction between a pyrazolyl derivative containing a carboxylic acid and several amine substrates. The molecular structures were determined by various spectroscopic methods, such as NMR (1H, 13C and 19F), FT-IR and high-resolution mass spectrometry (HRMS). X-ray crystallographic analysis on the 4-fluorobenzyl derivative (2d) reveals the amide-O atom to reside to the opposite side of the molecule to the pyrazolyl-N and pyrrolyl-N atoms; in the molecular packing, helical chains feature amide-N‒H⋯N(pyrrolyl) hydrogen bonds. Density-functional theory (DFT) at the geometry-optimisation B3LYP/6-31G(d) level on the full series shows general agreement with the experimental structures. While the LUMO in each case is spread over the benz[e]indole pyrazolyl moiety, the HOMO spreads over the halogenated benzo-substituted amide moieties or is localised near the benz[e]indole pyrazolyl moieties. The MTT assay showed that 2e, exhibited the highest toxicity against a human colorectal carcinoma (HCT 116 cell line) without appreciable toxicity towards the normal human colon fibroblast (CCD-18Co cell line). Based on molecular docking calculations, the probable cytotoxic mechanism of 2e is through the DNA minor groove binding. Five new compounds of benz[ e ]indole pyrazolyl-substituted amides ( 2a–e ) were synthesised in low to good yields via the direct amide-coupling reaction between a pyrazolyl derivative containing a carboxylic acid and several amine substrates. The molecular structures were determined by various spectroscopic methods, such as NMR ( 1 H, 13 C and 19 F), FT-IR and high-resolution mass spectrometry (HRMS). X-ray crystallographic analysis on the 4-fluorobenzyl derivative ( 2d ) reveals the amide- O atom to reside to the opposite side of the molecule to the pyrazolyl- N and pyrrolyl- N atoms; in the molecular packing, helical chains feature amide-N‒H⋯N(pyrrolyl) hydrogen bonds. Density-functional theory (DFT) at the geometry-optimisation B3LYP/6-31G(d) level on the full series shows general agreement with the experimental structures. While the LUMO in each case is spread over the benz[ e ]indole pyrazolyl moiety, the HOMO spreads over the halogenated benzo-substituted amide moieties or is localised near the benz[ e ]indole pyrazolyl moieties. The MTT assay showed that 2e , exhibited the highest toxicity against a human colorectal carcinoma (HCT 116 cell line) without appreciable toxicity towards the normal human colon fibroblast (CCD-18Co cell line). Based on molecular docking calculations, the probable cytotoxic mechanism of 2e is through the DNA minor groove binding. Graphical abstract
Author	Ng, Min Phin Fei, Chee Chin Ramle, Abdul Qaiyum Tan, Chun Hoe Sim, Kae Shin Tiekink, Edward R. T. Chan, Nadia Nabihah Mohd Yusof
Author_xml	– sequence: 1 givenname: Abdul Qaiyum surname: Ramle fullname: Ramle, Abdul Qaiyum email: qaiyum@usm.my organization: School of Chemical Sciences, Universiti Sains Malaysia – sequence: 2 givenname: Nadia Nabihah Mohd Yusof surname: Chan fullname: Chan, Nadia Nabihah Mohd Yusof organization: Department of Chemistry, Universiti Malaya – sequence: 3 givenname: Min Phin surname: Ng fullname: Ng, Min Phin organization: Institute of Biological Sciences, Faculty of Science, Universiti Malaya – sequence: 4 givenname: Chun Hoe surname: Tan fullname: Tan, Chun Hoe organization: Department of Biotechnology, Faculty of Applied Science, Lincoln University College – sequence: 5 givenname: Kae Shin surname: Sim fullname: Sim, Kae Shin organization: Institute of Biological Sciences, Faculty of Science, Universiti Malaya – sequence: 6 givenname: Edward R. T. surname: Tiekink fullname: Tiekink, Edward R. T. organization: Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University – sequence: 7 givenname: Chee Chin surname: Fei fullname: Fei, Chee Chin organization: Nanotechnology and Catalysis Research Centre, Universiti Malaya
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/37278911$$D View this record in MEDLINE/PubMed
BookMark	eNp9kEtLBDEQhIMo6qp_wIMMeI6mk9l5HEV8geBBBUGWkJnpaGQ2WZOMOPvrja6Pm6cu6Kpq-puQdessErIP7AgYK48DABOMMi4osKLglK-RbZiWgk4ZPKwnLSqgUNewRSYhvDCWYiA2yZYoeVnVANtkdhv90MbBqz4zNpin5xgyZbusHaOL7t20Jo4Zvql-UNE4mzmdNWiXjzgztnM9ZovRq6Xrx56GoQnRxCFil6m56TDskg2t-oB733OH3J-f3Z1e0uubi6vTk2vaipxHmjdNXkGBZVGjEE1Vp2ewbDQqKJPoVKHrSnDNoS0AWt0koQGrfCqmJVNa7JDDVe_Cu9cBQ5QvbvA2nZSCVTmwWhR1cvGVq_UuBI9aLryZKz9KYPKTqFwRlYmo_CIqeQodfFcPzRy738gPwmQQK0NIK_uE_u_2P7Ufk96E5w
CitedBy_id	crossref_primary_10_1016_j_bioorg_2024_107256 crossref_primary_10_1002_ardp_202400282
Cites_doi	10.1016/j.molstruc.2017.07.106 10.1002/ejoc.201300443 10.1016/j.jinorgbio.2020.111097 10.1016/j.bmcl.2014.04.094 10.1039/C6NJ03181A 10.1103/PhysRevB.37.785 10.1021/bi050021b 10.1038/s41598-023-32820-0 10.1016/j.dyepig.2022.110644 10.1016/j.solener.2021.08.033 10.1016/j.bioorg.2020.104141 10.1039/C7RA09858H 10.1016/j.saa.2017.03.045 10.1073/pnas.78.4.2179 10.1016/j.tranon.2022.101348 10.1016/j.dyepig.2019.01.009 10.1021/cr2000459 10.1002/slct.202004049 10.1002/ejic.201000412 10.3390/molecules18032683 10.3390/molecules171012187 10.1021/acs.jpca.8b02157 10.1107/S2056989019016244 10.1016/j.bioorg.2017.08.014 10.1055/a-1755-5605 10.1021/ol802931m 10.1021/ol8025022 10.1016/j.ejmech.2013.03.005 10.1016/j.solener.2018.09.039 10.1002/jhet.575 10.1021/cr60279a003 10.1016/j.molstruc.2016.06.070 10.1038/srep11544 10.1021/jf204778v 10.1107/S0021889812029111 10.1021/acs.joc.7b02460 10.1016/j.tetlet.2010.12.034 10.1016/j.ejmech.2017.07.059 10.1002/jhet.5570430624 10.1016/j.molstruc.2021.131067 10.1039/C8NJ02541J 10.1016/j.jfluchem.2019.109346 10.1016/S0968-0896(00)00088-2 10.1107/S0108767307043930 10.1002/jhet.18 10.1039/D0NJ04357E 10.1039/D0CE01054E 10.2174/138161210791209009 10.1186/1752-153X-6-163 10.1021/acs.jpca.0c10788 10.1016/j.bioorg.2019.103470 10.1016/j.jphotochem.2018.11.033 10.1107/S2053229614024218 10.1021/acs.jafc.0c00062 10.1016/j.bioorg.2022.106273 10.1016/j.molstruc.2019.127633 10.1016/j.sjbs.2015.07.005 10.1039/D0RA02394A 10.1039/C6RA10989F
ContentType	Journal Article
Copyright	The Author(s), under exclusive licence to Springer Nature Switzerland AG 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG.
Copyright_xml	– notice: The Author(s), under exclusive licence to Springer Nature Switzerland AG 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. – notice: 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG.
DBID	CGR CUY CVF ECM EIF NPM AAYXX CITATION K9.
DOI	10.1007/s11030-023-10662-2
DatabaseName	Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef ProQuest Health & Medical Complete (Alumni)
DatabaseTitle	MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef ProQuest Health & Medical Complete (Alumni)
DatabaseTitleList	MEDLINE ProQuest Health & Medical Complete (Alumni)
Database_xml	– sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database
DeliveryMethod	fulltext_linktorsrc
Discipline	Biology Physics
EISSN	1573-501X
EndPage	1376
ExternalDocumentID	10_1007_s11030_023_10662_2 37278911
Genre	Journal Article
GrantInformation_xml	– fundername: Universiti Sains Malaysia grantid: 304/PKIMIA/6315738 funderid: http://dx.doi.org/10.13039/501100004595 – fundername: Sunway University grantid: GRTIN-RRO-56-2022 funderid: http://dx.doi.org/10.13039/501100010798 – fundername: Sunway University grantid: GRTIN-RRO-56-2022 – fundername: Universiti Sains Malaysia grantid: 304/PKIMIA/6315738
GroupedDBID	--- -4W -58 -5G -BR -EM -Y2 -~C .86 .VR 06C 06D 0R~ 0VY 123 1SB 2.D 203 28- 29M 29~ 2J2 2JN 2JY 2KG 2KM 2LR 2P1 2VQ 2~H 30V 3SX 3V. 4.4 406 408 409 40E 53G 5QI 5VS 67Z 6NX 7X7 88E 88I 8FE 8FH 8FI 8FJ 8TC 8UJ 95- 95. 95~ 96X AAAVM AABHQ AACDK AAEOY AAHNG AAIAL AAJBT AAJKR AANXM AANZL AAQLM AARHV AARTL AASML AATNV AATVU AAUYE AAWCG AAYIU AAYQN AAYTO ABAKF ABBBX ABBXA ABDZT ABECU ABFGW ABFTV ABHLI ABHQN ABJNI ABJOX ABKAS ABKCH ABKTR ABMNI ABMQK ABNWP ABPLI ABQBU ABSXP ABTEG ABTHY ABTKH ABTMW ABULA ABUWG ABWNU ABXPI ACAOD ACBXY ACDTI ACGFS ACGOD ACHSB ACHXU ACIGE ACIPQ ACKNC ACMDZ ACMLO ACOKC ACOMO ACSNA ACTTH ACVWB ACWMK ACZOJ ADBBV ADHHG ADHIR ADIMF ADINQ ADKNI ADKPE ADOAH ADOXG ADRFC ADTPH ADURQ ADYFF ADYPR ADZKW AEBTG AEEQQ AEFIE AEFQL AEFTE AEGAL AEGNC AEJHL AEJRE AEKMD AEMSY AENEX AEOHA AEPYU AESKC AESTI AETLH AEVLU AEVTX AEXYK AFBBN AFEXP AFGCZ AFKRA AFLOW AFQWF AFWTZ AFZKB AGAYW AGDGC AGGDS AGJBK AGMZJ AGQEE AGQMX AGRTI AGWIL AGWZB AGYKE AHAVH AHBYD AHMBA AHSBF AHYZX AIAKS AIGIU AIIXL AILAN AIMYW AITGF AJBLW AJRNO AJZVZ AKMHD AKQUC ALIPV ALMA_UNASSIGNED_HOLDINGS ALWAN AMKLP AMXSW AMYLF AMYQR AOCGG ARMRJ ASPBG AVWKF AXYYD AZFZN AZQEC B-. BA0 BBWZM BDATZ BENPR BGNMA BPHCQ BVXVI CAG CCPQU COF CS3 CSCUP DDRTE DL5 DNIVK DPUIP DU5 DWQXO EBD EBLON EBS EIOEI EJD EMOBN EPAXT ESBYG F5P FEDTE FERAY FFXSO FIGPU FINBP FNLPD FRRFC FSGXE FWDCC FYUFA G-Y G-Z GGCAI GGRSB GJIRD GNUQQ GNWQR GQ6 GQ7 GQ8 GXS HCIFZ HF~ HG5 HG6 HMCUK HMJXF HQYDN HRMNR HVGLF HZ~ I09 IHE IJ- IKXTQ IWAJR IXC IXD IXE IZIGR IZQ I~X I~Z J-C J0Z JBSCW JCJTX JZLTJ KDC KOV KOW LAK LK5 LLZTM M1P M2P M4Y M7R MA- N2Q NB0 NDZJH NPVJJ NQJWS NU0 O9- O93 O9G O9I O9J OAM OVD P19 P9N PF0 PQQKQ PROAC PSQYO PT4 PT5 Q2X QOK QOR QOS R4E R89 R9I RHV RIG RNI RNS ROL RPX RRX RSV RZC RZE RZK S16 S1Z S26 S27 S28 S3B SAP SBY SCLPG SCM SDH SDM SHX SISQX SJYHP SNE SNPRN SNX SOHCF SOJ SPISZ SRMVM SSLCW SSXJD STPWE SV3 SZN T13 T16 TEORI TSG TSK TSV TUC TUS U2A U9L UG4 UKHRP UNUBA UOJIU UTJUX UZXMN VC2 VFIZW W23 W48 WJK WK6 WK8 YLTOR Z45 Z7U Z7V Z87 Z8O Z8P Z91 ZMTXR ZOVNA ~A9 ~EX ~KM AAYZH CGR CUY CVF ECM EIF H13 NPM AAYXX CITATION K9.
ID	FETCH-LOGICAL-c342t-4bb4816e769e33b89662e7bfea172e7da6f9832f21c611cfb21cf1e8453570af3
IEDL.DBID	U2A
ISSN	1381-1991
IngestDate	Thu Oct 10 22:40:18 EDT 2024 Tue Oct 29 03:08:48 EDT 2024 Sat Nov 02 12:01:35 EDT 2024 Thu Jul 25 06:23:15 EDT 2024
IsPeerReviewed	true
IsScholarly	true
Issue	3
Keywords	X-ray crystallography Cytotoxicity DFT Minor groove binding
Language	English
License	2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG.
LinkModel	DirectLink
MergedId	FETCHMERGED-LOGICAL-c342t-4bb4816e769e33b89662e7bfea172e7da6f9832f21c611cfb21cf1e8453570af3
PMID	37278911
PQID	3084109369
PQPubID	54625
PageCount	14
ParticipantIDs	proquest_journals_3084109369 crossref_primary_10_1007_s11030_023_10662_2 pubmed_primary_37278911 springer_journals_10_1007_s11030_023_10662_2
PublicationCentury	2000
PublicationDate	2024-06-01
PublicationDateYYYYMMDD	2024-06-01
PublicationDate_xml	– month: 06 year: 2024 text: 2024-06-01 day: 01
PublicationDecade	2020
PublicationPlace	Cham
PublicationPlace_xml	– name: Cham – name: Netherlands – name: Dordrecht
PublicationTitle	Molecular diversity
PublicationTitleAbbrev	Mol Divers
PublicationTitleAlternate	Mol Divers
PublicationYear	2024
Publisher	Springer International Publishing Springer Nature B.V
Publisher_xml	– name: Springer International Publishing – name: Springer Nature B.V
References	Kotecki, Fernando, Haight, Lukin (CR29) 2009; 11 Sheldrick (CR55) 2008; 64 Fu, Wang, Zhang, Hou, Gao, Zhao, Ye (CR14) 2017; 7 Zhang, Tan, Wang, Jing, Kang, Zhang (CR16) 2017; 1149 Madhu, Sivakumar (CR18) 2019; 371 Halim, Sharkawi, Labib (CR33) 2023; 131 Braden, Matta (CR46) 2018; 122 Abdelgawad, Labib, Abdel-Latif (CR5) 2017; 74 Baradarani, Afghan, Zebarjadi, Hasanzadeh, Joule (CR34) 2006; 43 Karrouchi, Fettach, Anouar, Tüzün, Radi, Alharthi, Ghabbour, Mabkhot, Faouzi, Ansar (CR42) 2021; 1245 Sheldrick (CR56) 2015; 71 Surendra Kumar, Arif, Ahamed, Idhayadhulla (CR6) 2016; 23 Gázquez (CR47) 2008; 52 Lin, Chen, Qiu, Zhu, Wang, Luo, Shi, Yang, Lei (CR25) 2020; 22 Yıldız, Güzel, Menges, Şişman, Kasım Şener (CR21) 2018; 174 Frezza, Hindo, Chen, Davenport, Schmitt, Tomco, Ping Dou (CR52) 2010; 16 Yu, Zhou, Cao, Hao, Yang, Guo, Zhang, Bakulev, Fan (CR3) 2020; 68 Yıldız, Ahmetali, Arslan, Menges, Nebioğlu, Şişman, Şener (CR23) 2022; 206 Prajapati, Pandey, Shimpi, Srivastava, Tandon, Velaga, Sinha (CR48) 2016; 1125 Yıldız, Arslan, Güzel, Nebioğlu, Menges, Şişman, Kasım Şener (CR22) 2021; 226 Ragab, Abdel Gawad, Georgey, Said (CR12) 2013; 63 Abraham, Prasana, Muthu (CR49) 2017; 181 Trofimenko (CR27) 1972; 72 Beaudoin, Wuest (CR30) 2011; 52 Xu, Gao, Ren, Song, Feng, Lv (CR9) 2017; 139 Jia, Lown (CR53) 2000; 8 Yang, Meng, Fang, Wang, Wang, Wang, Duan, Hao (CR20) 2018; 42 Hassan (CR4) 2013; 18 Lai, Yeh, Tsai, Cheng (CR45) 2013; 2013 Supruniuk, Czarnomysy, Muszyńska, Radziejewska (CR32) 2022; 18 Bennani, Doudach, Cherrah, Ramli, Karrouchi, Ansar, Faouzi (CR7) 2020; 97 Zahedifard, Lafta Faraj, Paydar, Yeng Looi, Hajrezaei, Hasanpourghadi, Kamalidehghan, Abdul Majid, Mohd Ali, Ameen Abdulla (CR38) 2015; 5 Ansari, Ali, Asif, Shamsuzzaman (CR2) 2017; 41 Wang, Liu, Peng, Huang, Gong, Li (CR8) 2020; 103 Liu, Cheng, Yu, Chen, Shao, Liu, Zhai, Yin (CR26) 2016; 6 Spek (CR58) 2020; 76 Tigreros, Portilla (CR17) 2020; 10 CR59 Heng, Sim, Tan (CR60) 2020; 208 CR54 Song, Liu, Xiong, Li, Yang, Wang (CR13) 2012; 60 Wu, Feng, Lin, Zhang (CR15) 2012; 17 Baruah, Wright, Bierbach (CR62) 2005; 44 El-Hazek, Zaher, Emam, El-Gazzar, Khalil (CR31) 2023; 13 Khan, Khalid, Gul, Shahzad, Tahir, Asif, Asim, Braga (CR44) 2020; 1205 Fustero, Sánchez-Roselló, Barrio, Simón-Fuentes (CR1) 2011; 111 Lee, Yang, Parr (CR43) 1988; 37 Bayguzina, Gallyamova, Khalilov, Khusnutdinov (CR41) 2019; 226 Khaledi, Ali, Thomas, Ng (CR36) 2011; 48 Viciano-Chumillas, Tanase, de Jongh, Reedijk (CR24) 2010; 2010 Sarkar, Chattaraj (CR50) 2021; 125 Farrugia (CR57) 2012; 45 Ramle, Khaledi, Hashim, Mingsukang, Mohd Arof, Ali, Basirun (CR40) 2019; 164 Ramle, Tiekink, Fei, Julkapli, Basirun (CR39) 2021; 45 Ebadi, Basirun, Khaledi, Ali (CR37) 2012; 6 Rashidi, Afghan, Baradarani, Joule (CR35) 2009; 46 Drew, Wing, Takano, Broka, Tanaka, Itakura, Dickerson (CR61) 1981; 78 Orrego-Hernández, Portilla (CR19) 2017; 82 Porzelle, Woodrow, Tomkinson (CR28) 2009; 11 Pathak, Maurya, Sharma, Srivastava, Gupta (CR10) 2014; 24 Moraes, Brum, Brusco, Marangoni, Lobo, Camargo, Nogara, Bonacorso, Martins, Da Rocha (CR11) 2020; 5 Tan, Sim, Lim, Mohd Mohidin, Mohan, Low, Kam, Sim (CR51) 2022 CS Abraham (10662_CR49) 2017; 181 S Fustero (10662_CR1) 2011; 111 J Liu (10662_CR26) 2016; 6 P Prajapati (10662_CR48) 2016; 1125 AL Spek (10662_CR58) 2020; 76 M Zahedifard (10662_CR38) 2015; 5 Y Fu (10662_CR14) 2017; 7 M Ebadi (10662_CR37) 2012; 6 Y-Y Lai (10662_CR45) 2013; 2013 H Khaledi (10662_CR36) 2011; 48 B Yıldız (10662_CR22) 2021; 226 GM Sheldrick (10662_CR55) 2008; 64 PA Moraes (10662_CR11) 2020; 5 G Yang (10662_CR20) 2018; 42 MM Baradarani (10662_CR34) 2006; 43 C-L Lin (10662_CR25) 2020; 22 H Baruah (10662_CR62) 2005; 44 G Wang (10662_CR8) 2020; 103 V Pathak (10662_CR10) 2014; 24 BJ Kotecki (10662_CR29) 2009; 11 S Trofimenko (10662_CR27) 1972; 72 AQ Ramle (10662_CR40) 2019; 164 B Yıldız (10662_CR23) 2022; 206 10662_CR54 FE Bennani (10662_CR7) 2020; 97 GM Sheldrick (10662_CR56) 2015; 71 10662_CR59 Z Xu (10662_CR9) 2017; 139 JL Gázquez (10662_CR47) 2008; 52 HR Drew (10662_CR61) 1981; 78 E Khan (10662_CR44) 2020; 1205 M Viciano-Chumillas (10662_CR24) 2010; 2010 PA Halim (10662_CR33) 2023; 131 K Supruniuk (10662_CR32) 2022; 18 A Ansari (10662_CR2) 2017; 41 J Zhang (10662_CR16) 2017; 1149 A Rashidi (10662_CR35) 2009; 46 LJ Farrugia (10662_CR57) 2012; 45 AQ Ramle (10662_CR39) 2021; 45 R Surendra Kumar (10662_CR6) 2016; 23 A Tigreros (10662_CR17) 2020; 10 MP Heng (10662_CR60) 2020; 208 MA Abdelgawad (10662_CR5) 2017; 74 SY Hassan (10662_CR4) 2013; 18 H Song (10662_CR13) 2012; 60 P Madhu (10662_CR18) 2019; 371 M Frezza (10662_CR52) 2010; 16 H Wu (10662_CR15) 2012; 17 D Beaudoin (10662_CR30) 2011; 52 AR Bayguzina (10662_CR41) 2019; 226 U Sarkar (10662_CR50) 2021; 125 DA Braden (10662_CR46) 2018; 122 J Orrego-Hernández (10662_CR19) 2017; 82 C Lee (10662_CR43) 1988; 37 RMM El-Hazek (10662_CR31) 2023; 13 K Karrouchi (10662_CR42) 2021; 1245 A Porzelle (10662_CR28) 2009; 11 CH Tan (10662_CR51) 2022 B Yu (10662_CR3) 2020; 68 FA Ragab (10662_CR12) 2013; 63 B Yıldız (10662_CR21) 2018; 174 G Jia (10662_CR53) 2000; 8
References_xml	– volume: 1149 start-page: 235 year: 2017 end-page: 242 ident: CR16 article-title: Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1 -Pyrazoles derivatives publication-title: J Mol Struct doi: 10.1016/j.molstruc.2017.07.106 contributor: fullname: Zhang – volume: 2013 start-page: 5076 year: 2013 end-page: 5084 ident: CR45 article-title: Synthesis, molecular and photovoltaic properties of an indolo[3,2- ]indole-based acceptor–donor–acceptor small molecule publication-title: Eur J Org Chem doi: 10.1002/ejoc.201300443 contributor: fullname: Cheng – volume: 208 start-page: 111097 year: 2020 ident: CR60 article-title: Nickel and zinc complexes of testosterone N4-substituted thiosemicarbazone: Selective cytotoxicity towards human colorectal carcinoma cell line HCT 116 and their cell death mechanisms publication-title: J Inorg Biochem doi: 10.1016/j.jinorgbio.2020.111097 contributor: fullname: Tan – volume: 24 start-page: 2892 year: 2014 end-page: 2896 ident: CR10 article-title: Synthesis and biological evaluation of substituted 4,6-diarylpyrimidines and 3,5-diphenyl-4,5-dihydro-1 -pyrazoles as anti-tubercular agents publication-title: Bioorg Med Chem Lett doi: 10.1016/j.bmcl.2014.04.094 contributor: fullname: Gupta – volume: 41 start-page: 16 year: 2017 end-page: 41 ident: CR2 article-title: Review: biologically active pyrazole derivatives publication-title: New J Chem doi: 10.1039/C6NJ03181A contributor: fullname: Shamsuzzaman – volume: 37 start-page: 785 year: 1988 end-page: 789 ident: CR43 article-title: Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density publication-title: Phys Rev B doi: 10.1103/PhysRevB.37.785 contributor: fullname: Parr – volume: 52 start-page: 3 year: 2008 end-page: 10 ident: CR47 article-title: Perspectives on the density functional theory of chemical reactivity publication-title: J Mex Chem Soc contributor: fullname: Gázquez – volume: 44 start-page: 6059 year: 2005 end-page: 6070 ident: CR62 article-title: Solution structural study of a DNA duplex containing the guanine-N7 adduct formed by a cytotoxic platinum−acridine hybrid agent publication-title: Biochem doi: 10.1021/bi050021b contributor: fullname: Bierbach – volume: 13 start-page: 5782 year: 2023 ident: CR31 article-title: Pyrazole-sulfonamide scaffold featuring dual-tail strategy as apoptosis inducers in colon cancer publication-title: Sci Rep doi: 10.1038/s41598-023-32820-0 contributor: fullname: Khalil – volume: 206 start-page: 110644 year: 2022 ident: CR23 article-title: Effect of direct linkage of pyrazole carboxylic acid acceptor/anchoring group on the photovoltaic performance for phthalocyanine-sensitized solar cells publication-title: Dyes Pigm doi: 10.1016/j.dyepig.2022.110644 contributor: fullname: Şener – volume: 226 start-page: 173 year: 2021 end-page: 179 ident: CR22 article-title: Non-aggregating zinc phthalocyanine sensitizer with bulky diphenylphenoxy donor groups and pyrazole-3-carboxylic acid anchoring group for coadsorbent-free dye-sensitized solar cells publication-title: Sol Energy doi: 10.1016/j.solener.2021.08.033 contributor: fullname: Kasım Şener – volume: 103 start-page: 104141 year: 2020 ident: CR8 article-title: Design, synthesis, molecular modeling, and biological evaluation of pyrazole-naphthalene derivatives as potential anticancer agents on MCF-7 breast cancer cells by inhibiting tubulin polymerization publication-title: Bioorg Chem doi: 10.1016/j.bioorg.2020.104141 contributor: fullname: Li – ident: CR54 – volume: 7 start-page: 46858 year: 2017 end-page: 46865 ident: CR14 article-title: Design, synthesis, and herbicidal activity of pyrazole benzophenone derivatives publication-title: RSC Adv doi: 10.1039/C7RA09858H contributor: fullname: Ye – volume: 181 start-page: 153 year: 2017 end-page: 163 ident: CR49 article-title: Quantum mechanical, spectroscopic and docking studies of 2-amino-3-bromo-5-nitropyridine by density functional method publication-title: Spectrochim Acta A doi: 10.1016/j.saa.2017.03.045 contributor: fullname: Muthu – volume: 78 start-page: 2179 year: 1981 end-page: 2183 ident: CR61 article-title: Structure of a B-DNA dodecamer: conformation and dynamics publication-title: Proc Natl Acad Sci USA doi: 10.1073/pnas.78.4.2179 contributor: fullname: Dickerson – volume: 18 start-page: 101348 year: 2022 ident: CR32 article-title: Anti-cancer effects of pyrazole-platinum(II) complexes combined with anti-MUC1 monoclonal antibody versus monotherapy in DLD-1 and HT-29 colon cancer cells publication-title: Transl Oncol doi: 10.1016/j.tranon.2022.101348 contributor: fullname: Radziejewska – volume: 164 start-page: 112 year: 2019 end-page: 118 ident: CR40 article-title: Indolenine–dibenzotetraaza [14] annulene Ni (II) complexes as sensitizers for dye-sensitized solar cells publication-title: Dyes Pigm doi: 10.1016/j.dyepig.2019.01.009 contributor: fullname: Basirun – volume: 111 start-page: 6984 year: 2011 end-page: 7034 ident: CR1 article-title: From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles publication-title: Chem Rev doi: 10.1021/cr2000459 contributor: fullname: Simón-Fuentes – volume: 5 start-page: 14620 year: 2020 end-page: 14625 ident: CR11 article-title: Pyrazole-enaminones as promising prototypes for the development of analgesic drugs publication-title: ChemistrySelect doi: 10.1002/slct.202004049 contributor: fullname: Da Rocha – volume: 2010 start-page: 3403 year: 2010 end-page: 3418 ident: CR24 article-title: Coordination versatility of pyrazole-based ligands towards high-nuclearity transition-metal and rare-earth clusters publication-title: Eur J Inorg Chem doi: 10.1002/ejic.201000412 contributor: fullname: Reedijk – volume: 18 start-page: 2683 year: 2013 end-page: 2711 ident: CR4 article-title: Synthesis, antibacterial and antifungal activity of some new pyrazoline and pyrazole derivatives publication-title: Molecules doi: 10.3390/molecules18032683 contributor: fullname: Hassan – volume: 17 start-page: 12187 year: 2012 end-page: 12196 ident: CR15 article-title: Synthesis and herbicidal activity of substituted pyrazole isothiocyanates publication-title: Molecules doi: 10.3390/molecules171012187 contributor: fullname: Zhang – volume: 122 start-page: 4538 year: 2018 end-page: 4548 ident: CR46 article-title: On the unusual synclinal conformations of hexafluorobutadiene and structurally similar molecules publication-title: J Phys Chem A doi: 10.1021/acs.jpca.8b02157 contributor: fullname: Matta – volume: 76 start-page: 1 year: 2020 end-page: 11 ident: CR58 article-title: checkCIF validation ALERTS: what they mean and how to respond publication-title: Acta Crystallogr E doi: 10.1107/S2056989019016244 contributor: fullname: Spek – volume: 74 start-page: 212 year: 2017 end-page: 220 ident: CR5 article-title: Pyrazole-hydrazone derivatives as anti-inflammatory agents: design, synthesis, biological evaluation, COX-1,2/5-LOX inhibition and docking study publication-title: Bioorg Chem doi: 10.1016/j.bioorg.2017.08.014 contributor: fullname: Abdel-Latif – year: 2022 ident: CR51 article-title: Antiproliferative and microtubule-stabilizing activities of two iboga-vobasine bisindoles alkaloids from tabernaemontana corymbosa in colorectal adenocarcinoma HT-29 cells publication-title: Planta Med doi: 10.1055/a-1755-5605 contributor: fullname: Sim – volume: 11 start-page: 947 year: 2009 end-page: 950 ident: CR29 article-title: A general method for the synthesis of unsymmetrically substituted ureas via palladium-catalyzed amidation publication-title: Org Lett doi: 10.1021/ol802931m contributor: fullname: Lukin – volume: 11 start-page: 233 year: 2009 end-page: 236 ident: CR28 article-title: Palladium-catalyzed coupling of hydroxylamines with aryl bromides, chlorides, and iodides publication-title: Org Lett doi: 10.1021/ol8025022 contributor: fullname: Tomkinson – volume: 63 start-page: 645 year: 2013 end-page: 654 ident: CR12 article-title: Synthesis of novel 1,3,4-trisubstituted pyrazoles as anti-inflammatory and analgesic agents publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2013.03.005 contributor: fullname: Said – volume: 174 start-page: 527 year: 2018 end-page: 536 ident: CR21 article-title: Pyrazole-3-carboxylic acid as a new anchoring group for phthalocyanine-sensitized solar cells publication-title: Sol Energy doi: 10.1016/j.solener.2018.09.039 contributor: fullname: Kasım Şener – volume: 48 start-page: 663 year: 2011 end-page: 670 ident: CR36 article-title: Reactions of 2-(diformylmethylidene)-3,3-dimethylindole with hydrazides: Synthesis of new pyrazolylindolenine derivatives—the unprecedented one-pot pyrazole–thiadiazole double annulation publication-title: J Heterocycl Chem doi: 10.1002/jhet.575 contributor: fullname: Ng – volume: 72 start-page: 497 year: 1972 end-page: 509 ident: CR27 article-title: Coordination chemistry of pyrazole-derived ligands publication-title: Chem Rev doi: 10.1021/cr60279a003 contributor: fullname: Trofimenko – volume: 1125 start-page: 193 year: 2016 end-page: 203 ident: CR48 article-title: Combined spectroscopic and quantum chemical studies of ezetimibe publication-title: J Mol Struct doi: 10.1016/j.molstruc.2016.06.070 contributor: fullname: Sinha – volume: 5 start-page: 11544 year: 2015 ident: CR38 article-title: Synthesis, characterization and apoptotic activity of quinazolinone Schiff base derivatives toward MCF-7 cells via intrinsic and extrinsic apoptosis pathways publication-title: Sci Rep doi: 10.1038/srep11544 contributor: fullname: Ameen Abdulla – volume: 60 start-page: 1470 year: 2012 end-page: 1479 ident: CR13 article-title: Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl- -benzyl carboxamide, α-chloromethyl- -benzyl carboxamide, and 4,5-dihydrooxazole moieties publication-title: J Agric Food Chem doi: 10.1021/jf204778v contributor: fullname: Wang – volume: 45 start-page: 849 year: 2012 end-page: 854 ident: CR57 article-title: WinGX and ORTEP for Windows: an update publication-title: J Appl Crystallogr doi: 10.1107/S0021889812029111 contributor: fullname: Farrugia – volume: 82 start-page: 13376 year: 2017 end-page: 13385 ident: CR19 article-title: Synthesis of dicyanovinyl-substituted 1-(2-pyridyl)pyrazoles: design of a fluorescent chemosensor for selective recognition of cyanide publication-title: J Org Chem doi: 10.1021/acs.joc.7b02460 contributor: fullname: Portilla – volume: 52 start-page: 2221 year: 2011 end-page: 2223 ident: CR30 article-title: Synthesis of -arylhydroxylamines by Pd-catalyzed coupling publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2010.12.034 contributor: fullname: Wuest – volume: 139 start-page: 429 year: 2017 end-page: 440 ident: CR9 article-title: Recent advances of pyrazole-containing derivatives as anti-tubercular agents publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2017.07.059 contributor: fullname: Lv – volume: 43 start-page: 1591 year: 2006 end-page: 1595 ident: CR34 article-title: The synthesis of 3,3-dimethyl-2-(1-aryl-1 -pyrazol-4-yl)-3 -indoles publication-title: J Heterocycl Chem doi: 10.1002/jhet.5570430624 contributor: fullname: Joule – volume: 1245 start-page: 131067 year: 2021 ident: CR42 article-title: Synthesis, crystal structure, DFT, α-glucosidase and α-amylase inhibition and molecular docking studies of (E)- '-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide publication-title: J Mol Struct doi: 10.1016/j.molstruc.2021.131067 contributor: fullname: Ansar – volume: 42 start-page: 14630 year: 2018 end-page: 14641 ident: CR20 article-title: Two novel pyrazole-based chemosensors: “naked-eye” colorimetric recognition of Ni and Al in alcohol and aqueous DMF media publication-title: New J Chem doi: 10.1039/C8NJ02541J contributor: fullname: Hao – volume: 226 start-page: 109346 year: 2019 ident: CR41 article-title: Synthesis of mono- and difluorobenzyl chlorides by chlorination of mono- and difluorotoluenes with CCl and -BuOCl induced by iron-containing catalysts publication-title: J Fluo Chem doi: 10.1016/j.jfluchem.2019.109346 contributor: fullname: Khusnutdinov – volume: 8 start-page: 1607 year: 2000 end-page: 1617 ident: CR53 article-title: Design, synthesis and cytotoxicity evaluation of 1-chloromethyl-5-hydroxy-1,2-dihydro-3 -benz[ ]indole ( -CBI) dimers publication-title: Bioorg Med Chem doi: 10.1016/S0968-0896(00)00088-2 contributor: fullname: Lown – volume: 64 start-page: 112 year: 2008 end-page: 122 ident: CR55 article-title: A short history of SHELX publication-title: Acta Crystallogr A doi: 10.1107/S0108767307043930 contributor: fullname: Sheldrick – volume: 46 start-page: 428 year: 2009 end-page: 431 ident: CR35 article-title: The synthesis of 4-(3,3-dimethyl-3 -pyrrolo[2,3- ]quinolin-2-yl)pyrazoles and 4-(3,3-dimethyl-3 -pyrrolo[3,2- ]quinolin-2-yl)pyrazoles publication-title: J Heterocycl Chem doi: 10.1002/jhet.18 contributor: fullname: Joule – volume: 45 start-page: 1221 year: 2021 end-page: 1230 ident: CR39 article-title: Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions publication-title: New J Chem doi: 10.1039/D0NJ04357E contributor: fullname: Basirun – volume: 22 start-page: 6847 year: 2020 end-page: 6855 ident: CR25 article-title: Synthesis, structure and photocatalytic properties of coordination polymers based on pyrazole carboxylic acid ligands publication-title: CrystEngComm doi: 10.1039/D0CE01054E contributor: fullname: Lei – volume: 16 start-page: 1813 year: 2010 end-page: 1825 ident: CR52 article-title: Novel metals and metal complexes as platforms for cancer therapy publication-title: Curr Pharm Des doi: 10.2174/138161210791209009 contributor: fullname: Ping Dou – volume: 6 start-page: 163 year: 2012 ident: CR37 article-title: Corrosion inhibition properties of pyrazolylindolenine compounds on copper surface in acidic media publication-title: Chem Cent J doi: 10.1186/1752-153X-6-163 contributor: fullname: Ali – volume: 125 start-page: 2051 year: 2021 end-page: 2060 ident: CR50 article-title: Reactivity dynamics publication-title: J Phys Chem A doi: 10.1021/acs.jpca.0c10788 contributor: fullname: Chattaraj – volume: 97 start-page: 103470 year: 2020 ident: CR7 article-title: Overview of recent developments of pyrazole derivatives as an anticancer agent in different cell line publication-title: Bioorg Chem doi: 10.1016/j.bioorg.2019.103470 contributor: fullname: Faouzi – volume: 371 start-page: 341 year: 2019 end-page: 348 ident: CR18 article-title: A novel pyridine-pyrazole based selective "turn-off" fluorescent chemosensor for Fe(III) ions publication-title: J Photochem Photobiol A doi: 10.1016/j.jphotochem.2018.11.033 contributor: fullname: Sivakumar – volume: 71 start-page: 3 year: 2015 end-page: 8 ident: CR56 article-title: Crystal structure refinement with SHELXL publication-title: Acta Crystallogr C doi: 10.1107/S2053229614024218 contributor: fullname: Sheldrick – ident: CR59 – volume: 68 start-page: 7093 year: 2020 end-page: 7102 ident: CR3 article-title: Design, synthesis, and evaluation of the antifungal activity of novel pyrazole–thiazole carboxamides as succinate dehydrogenase inhibitors publication-title: J Agric Food Chem doi: 10.1021/acs.jafc.0c00062 contributor: fullname: Fan – volume: 131 start-page: 106273 year: 2023 ident: CR33 article-title: Novel pyrazole-based COX-2 inhibitors as potential anticancer agents: design, synthesis, cytotoxic effect against resistant cancer cells, cell cycle arrest, apoptosis induction and dual EGFR/Topo-1 inhibition publication-title: Bioorg Chem doi: 10.1016/j.bioorg.2022.106273 contributor: fullname: Labib – volume: 1205 start-page: 127633 year: 2020 ident: CR44 article-title: Molecular structure of 1,4-bis(substituted-carbonyl)benzene: a combined experimental and theoretical approach publication-title: J Mol Struct doi: 10.1016/j.molstruc.2019.127633 contributor: fullname: Braga – volume: 23 start-page: 614 year: 2016 end-page: 620 ident: CR6 article-title: Anti-inflammatory and antimicrobial activities of novel pyrazole analogues publication-title: Saudi J Biol Sci doi: 10.1016/j.sjbs.2015.07.005 contributor: fullname: Idhayadhulla – volume: 10 start-page: 19693 year: 2020 end-page: 19712 ident: CR17 article-title: Recent progress in chemosensors based on pyrazole derivatives publication-title: RSC Adv doi: 10.1039/D0RA02394A contributor: fullname: Portilla – volume: 6 start-page: 52040 year: 2016 end-page: 52047 ident: CR26 article-title: Three metal complexes derived from 3-methyl-1 -pyrazole-4-carboxylic acid: synthesis, crystal structures, luminescence and electrocatalytic properties publication-title: RSC Adv doi: 10.1039/C6RA10989F contributor: fullname: Yin – volume: 7 start-page: 46858 year: 2017 ident: 10662_CR14 publication-title: RSC Adv doi: 10.1039/C7RA09858H contributor: fullname: Y Fu – ident: 10662_CR54 – volume: 45 start-page: 849 year: 2012 ident: 10662_CR57 publication-title: J Appl Crystallogr doi: 10.1107/S0021889812029111 contributor: fullname: LJ Farrugia – volume: 78 start-page: 2179 year: 1981 ident: 10662_CR61 publication-title: Proc Natl Acad Sci USA doi: 10.1073/pnas.78.4.2179 contributor: fullname: HR Drew – volume: 164 start-page: 112 year: 2019 ident: 10662_CR40 publication-title: Dyes Pigm doi: 10.1016/j.dyepig.2019.01.009 contributor: fullname: AQ Ramle – volume: 60 start-page: 1470 year: 2012 ident: 10662_CR13 publication-title: J Agric Food Chem doi: 10.1021/jf204778v contributor: fullname: H Song – volume: 82 start-page: 13376 year: 2017 ident: 10662_CR19 publication-title: J Org Chem doi: 10.1021/acs.joc.7b02460 contributor: fullname: J Orrego-Hernández – volume: 72 start-page: 497 year: 1972 ident: 10662_CR27 publication-title: Chem Rev doi: 10.1021/cr60279a003 contributor: fullname: S Trofimenko – volume: 8 start-page: 1607 year: 2000 ident: 10662_CR53 publication-title: Bioorg Med Chem doi: 10.1016/S0968-0896(00)00088-2 contributor: fullname: G Jia – volume: 68 start-page: 7093 year: 2020 ident: 10662_CR3 publication-title: J Agric Food Chem doi: 10.1021/acs.jafc.0c00062 contributor: fullname: B Yu – volume: 208 start-page: 111097 year: 2020 ident: 10662_CR60 publication-title: J Inorg Biochem doi: 10.1016/j.jinorgbio.2020.111097 contributor: fullname: MP Heng – volume: 13 start-page: 5782 year: 2023 ident: 10662_CR31 publication-title: Sci Rep doi: 10.1038/s41598-023-32820-0 contributor: fullname: RMM El-Hazek – volume: 52 start-page: 2221 year: 2011 ident: 10662_CR30 publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2010.12.034 contributor: fullname: D Beaudoin – volume: 11 start-page: 233 year: 2009 ident: 10662_CR28 publication-title: Org Lett doi: 10.1021/ol8025022 contributor: fullname: A Porzelle – volume: 206 start-page: 110644 year: 2022 ident: 10662_CR23 publication-title: Dyes Pigm doi: 10.1016/j.dyepig.2022.110644 contributor: fullname: B Yıldız – volume: 18 start-page: 101348 year: 2022 ident: 10662_CR32 publication-title: Transl Oncol doi: 10.1016/j.tranon.2022.101348 contributor: fullname: K Supruniuk – volume: 24 start-page: 2892 year: 2014 ident: 10662_CR10 publication-title: Bioorg Med Chem Lett doi: 10.1016/j.bmcl.2014.04.094 contributor: fullname: V Pathak – volume: 6 start-page: 163 year: 2012 ident: 10662_CR37 publication-title: Chem Cent J doi: 10.1186/1752-153X-6-163 contributor: fullname: M Ebadi – volume: 11 start-page: 947 year: 2009 ident: 10662_CR29 publication-title: Org Lett doi: 10.1021/ol802931m contributor: fullname: BJ Kotecki – volume: 122 start-page: 4538 year: 2018 ident: 10662_CR46 publication-title: J Phys Chem A doi: 10.1021/acs.jpca.8b02157 contributor: fullname: DA Braden – volume: 41 start-page: 16 year: 2017 ident: 10662_CR2 publication-title: New J Chem doi: 10.1039/C6NJ03181A contributor: fullname: A Ansari – volume: 46 start-page: 428 year: 2009 ident: 10662_CR35 publication-title: J Heterocycl Chem doi: 10.1002/jhet.18 contributor: fullname: A Rashidi – volume: 103 start-page: 104141 year: 2020 ident: 10662_CR8 publication-title: Bioorg Chem doi: 10.1016/j.bioorg.2020.104141 contributor: fullname: G Wang – volume: 42 start-page: 14630 year: 2018 ident: 10662_CR20 publication-title: New J Chem doi: 10.1039/C8NJ02541J contributor: fullname: G Yang – volume: 18 start-page: 2683 year: 2013 ident: 10662_CR4 publication-title: Molecules doi: 10.3390/molecules18032683 contributor: fullname: SY Hassan – volume: 48 start-page: 663 year: 2011 ident: 10662_CR36 publication-title: J Heterocycl Chem doi: 10.1002/jhet.575 contributor: fullname: H Khaledi – volume: 111 start-page: 6984 year: 2011 ident: 10662_CR1 publication-title: Chem Rev doi: 10.1021/cr2000459 contributor: fullname: S Fustero – volume: 23 start-page: 614 year: 2016 ident: 10662_CR6 publication-title: Saudi J Biol Sci doi: 10.1016/j.sjbs.2015.07.005 contributor: fullname: R Surendra Kumar – volume: 63 start-page: 645 year: 2013 ident: 10662_CR12 publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2013.03.005 contributor: fullname: FA Ragab – volume: 174 start-page: 527 year: 2018 ident: 10662_CR21 publication-title: Sol Energy doi: 10.1016/j.solener.2018.09.039 contributor: fullname: B Yıldız – volume: 10 start-page: 19693 year: 2020 ident: 10662_CR17 publication-title: RSC Adv doi: 10.1039/D0RA02394A contributor: fullname: A Tigreros – volume: 131 start-page: 106273 year: 2023 ident: 10662_CR33 publication-title: Bioorg Chem doi: 10.1016/j.bioorg.2022.106273 contributor: fullname: PA Halim – volume: 76 start-page: 1 year: 2020 ident: 10662_CR58 publication-title: Acta Crystallogr E doi: 10.1107/S2056989019016244 contributor: fullname: AL Spek – volume: 125 start-page: 2051 year: 2021 ident: 10662_CR50 publication-title: J Phys Chem A doi: 10.1021/acs.jpca.0c10788 contributor: fullname: U Sarkar – volume: 1149 start-page: 235 year: 2017 ident: 10662_CR16 publication-title: J Mol Struct doi: 10.1016/j.molstruc.2017.07.106 contributor: fullname: J Zhang – volume: 181 start-page: 153 year: 2017 ident: 10662_CR49 publication-title: Spectrochim Acta A doi: 10.1016/j.saa.2017.03.045 contributor: fullname: CS Abraham – volume: 1205 start-page: 127633 year: 2020 ident: 10662_CR44 publication-title: J Mol Struct doi: 10.1016/j.molstruc.2019.127633 contributor: fullname: E Khan – volume: 74 start-page: 212 year: 2017 ident: 10662_CR5 publication-title: Bioorg Chem doi: 10.1016/j.bioorg.2017.08.014 contributor: fullname: MA Abdelgawad – volume: 6 start-page: 52040 year: 2016 ident: 10662_CR26 publication-title: RSC Adv doi: 10.1039/C6RA10989F contributor: fullname: J Liu – volume: 16 start-page: 1813 year: 2010 ident: 10662_CR52 publication-title: Curr Pharm Des doi: 10.2174/138161210791209009 contributor: fullname: M Frezza – volume: 44 start-page: 6059 year: 2005 ident: 10662_CR62 publication-title: Biochem doi: 10.1021/bi050021b contributor: fullname: H Baruah – volume: 371 start-page: 341 year: 2019 ident: 10662_CR18 publication-title: J Photochem Photobiol A doi: 10.1016/j.jphotochem.2018.11.033 contributor: fullname: P Madhu – volume: 2010 start-page: 3403 year: 2010 ident: 10662_CR24 publication-title: Eur J Inorg Chem doi: 10.1002/ejic.201000412 contributor: fullname: M Viciano-Chumillas – volume: 1245 start-page: 131067 year: 2021 ident: 10662_CR42 publication-title: J Mol Struct doi: 10.1016/j.molstruc.2021.131067 contributor: fullname: K Karrouchi – volume: 71 start-page: 3 year: 2015 ident: 10662_CR56 publication-title: Acta Crystallogr C doi: 10.1107/S2053229614024218 contributor: fullname: GM Sheldrick – year: 2022 ident: 10662_CR51 publication-title: Planta Med doi: 10.1055/a-1755-5605 contributor: fullname: CH Tan – volume: 45 start-page: 1221 year: 2021 ident: 10662_CR39 publication-title: New J Chem doi: 10.1039/D0NJ04357E contributor: fullname: AQ Ramle – volume: 22 start-page: 6847 year: 2020 ident: 10662_CR25 publication-title: CrystEngComm doi: 10.1039/D0CE01054E contributor: fullname: C-L Lin – volume: 2013 start-page: 5076 year: 2013 ident: 10662_CR45 publication-title: Eur J Org Chem doi: 10.1002/ejoc.201300443 contributor: fullname: Y-Y Lai – volume: 52 start-page: 3 year: 2008 ident: 10662_CR47 publication-title: J Mex Chem Soc contributor: fullname: JL Gázquez – volume: 64 start-page: 112 year: 2008 ident: 10662_CR55 publication-title: Acta Crystallogr A doi: 10.1107/S0108767307043930 contributor: fullname: GM Sheldrick – volume: 139 start-page: 429 year: 2017 ident: 10662_CR9 publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2017.07.059 contributor: fullname: Z Xu – volume: 43 start-page: 1591 year: 2006 ident: 10662_CR34 publication-title: J Heterocycl Chem doi: 10.1002/jhet.5570430624 contributor: fullname: MM Baradarani – volume: 5 start-page: 14620 year: 2020 ident: 10662_CR11 publication-title: ChemistrySelect doi: 10.1002/slct.202004049 contributor: fullname: PA Moraes – volume: 226 start-page: 109346 year: 2019 ident: 10662_CR41 publication-title: J Fluo Chem doi: 10.1016/j.jfluchem.2019.109346 contributor: fullname: AR Bayguzina – volume: 1125 start-page: 193 year: 2016 ident: 10662_CR48 publication-title: J Mol Struct doi: 10.1016/j.molstruc.2016.06.070 contributor: fullname: P Prajapati – volume: 37 start-page: 785 year: 1988 ident: 10662_CR43 publication-title: Phys Rev B doi: 10.1103/PhysRevB.37.785 contributor: fullname: C Lee – ident: 10662_CR59 – volume: 226 start-page: 173 year: 2021 ident: 10662_CR22 publication-title: Sol Energy doi: 10.1016/j.solener.2021.08.033 contributor: fullname: B Yıldız – volume: 17 start-page: 12187 year: 2012 ident: 10662_CR15 publication-title: Molecules doi: 10.3390/molecules171012187 contributor: fullname: H Wu – volume: 5 start-page: 11544 year: 2015 ident: 10662_CR38 publication-title: Sci Rep doi: 10.1038/srep11544 contributor: fullname: M Zahedifard – volume: 97 start-page: 103470 year: 2020 ident: 10662_CR7 publication-title: Bioorg Chem doi: 10.1016/j.bioorg.2019.103470 contributor: fullname: FE Bennani
SSID	ssj0010013
Score	2.4258192
Snippet	Five new compounds of benz[ e ]indole pyrazolyl-substituted amides ( 2a–e ) were synthesised in low to good yields via the direct amide-coupling reaction... Five new compounds of benz[e]indole pyrazolyl-substituted amides (2a-e) were synthesised in low to good yields via the direct amide-coupling reaction between a... Five new compounds of benz[e]indole pyrazolyl-substituted amides (2a–e) were synthesised in low to good yields via the direct amide-coupling reaction between a...
SourceID	proquest crossref pubmed springer
SourceType	Aggregation Database Index Database Publisher
StartPage	1363
SubjectTerms	Amides - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biochemistry Biomedical and Life Sciences Cell Line, Tumor Cell Survival - drug effects Crystallography, X-Ray HCT116 Cells Humans Indoles - chemistry Indoles - pharmacology Life Sciences Models, Molecular Molecular Docking Simulation Molecular Structure Organic Chemistry Original Article Pharmacy Polymer Sciences Pyrazoles - chemistry Pyrazoles - pharmacology Structure-Activity Relationship Toxicity
Title	Structural insights and cytotoxicity evaluation of benz[e]indole pyrazolyl-substituted amides
URI	https://link.springer.com/article/10.1007/s11030-023-10662-2 https://www.ncbi.nlm.nih.gov/pubmed/37278911 https://www.proquest.com/docview/3084109369
Volume	28
hasFullText	1
inHoldings	1
isFullTextHit
isPrint
link	http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3NS8MwFA-yIXgRv63OkYM3LSxp-nUcsjkUvehgIqMkaQKD2Q67g9tf70varsj04K2HNqW_l_fV994vCF2bnzWUCuGGgkKCwkDTeRhx19eSKg1OJ7azVU_PwWjMHib-pJnjts3udUXSGupm1s0ciOWCiwHLEQTUBbvb9g0dGmziMe1vSgcmqLFZVkRMFwWpJmV-X-OnN9oKMbfKo9brDA_QfhUu4n4p30O0o7IjtFseILmCK9vAKYtjNH2xRLCGRAPPssKk3AXmWYrlapkv86-ZhHAbN9zeONdYqGz9rqaQledzhRerT77O56u5W4AxKTsIUsw_ZqkqTtB4OHi9G7nV0Qmu9BhdukwIFpFAhUGsPE9EkNRQFQqtOAQsKkx5oGPQZU2JDAiRGgQlNVER8z0_7HHtnaJWlmfqHGFQehanoc_BmzMqKY_ilBLeS6X2epL4DrqpIUwWJUNG0nAhG8ATADyxgCfUQZ0a5aTSliLxehEztFZB7KCzEvnNUl5oZnUJcdBtLYrmwb_fc_G_2y_RHoXvK3vAOqgFIlNXEG0sRRe1-_dvj4Ou3WXfsF_Lig
link.rule.ids	315,783,787,27936,27937,41093,41535,42162,42604,52123,52246
linkProvider	Springer Nature
linkToHtml	http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3NS8MwFA-iiF7Eb6tTc_CmhSZNv45DHFO3XdxgIKMkaQKD2Q67g91f70s_NmR68NZDm9Lfy_vqe-8XhO7MzxpKhbADQSFBYaDpPAi57WlJlQanE5WzVf2B3x2xl7E3rofC8qbbvSlJlpZ6PexmTsSywceA6fB9aoPh3TH86oYxf0Tbq9qBiWrKNCskpo2C1KMyv6_x0x1txJgb9dHS7XQO0UEdL-J2JeAjtKXSY7RbnSBZwFXZwSnzEzR5K5lgDYsGnqa5yblzzNMEy2KRLbKvqYR4G6_JvXGmsVDp8l1NIC3PZgrPi0--zGbFzM7BmlQtBAnmH9NE5ado1HkaPnbt-uwEW7qMLmwmBAuJrwI_Uq4rQshqqAqEVhwiFhUk3NcRKLOmRPqESA2SkpqokHmuFzhcu2doO81SdYEwaD2LksDj4M4ZlZSHUUIJdxKpXUcSz0L3DYTxvKLIiNdkyAbwGACPS8BjaqFWg3Jcq0seu07IDK-VH1novEJ-tZQbmGFdQiz00Ihi_eDf77n83-23aK877Pfi3vPg9QrtU_jWqiGshbZBfOoaQo-FuCl32jctcM1R
linkToPdf	http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1LT-QwDLbQIBAXXrvA8NocuLGFSZq-jggY2OUhJEACIVQlaSKNgHZEi8TMr8fpg2F5HNDeemjTxnbsz439BWDD_qxhTEonkAwTFI4rXQShcDyjmDYYdKKyt-rk1D-85H-vvKs3XfxltXuzJVn1NFiWprTY7idme9T4Zk_HcjDeoBvxfeagEx7nlhmpBeM7B9dH-687CRbjlElXSG1RBa0bZz4f5d_g9AFxftgtLYNQdwZE8_lV7cnd1lMht9TwHbPj_8xvFqZrhEp2KpOagzGdzsNEdWblAK_KmlGV_4Db85J71vJ2kF6a2yw_JyJNiBoUWZE99xQifDKiEyeZIVKnwxt920stkRTpDx7FMLsf3Ds5-q-qaCEh4qGX6PwnXHb3L3YPnfq0Bke5nBUOl5KH1NeBH2nXlSHmUUwH0miBGEkHifBNhO7DMKp8SpVB21CG6pB7rhd0hHEXoJVmqV4Cgn6GR0ngCQQQnCkmwihhVHQSZdyOol4bNhs1xf2KlCMe0S9b0cUourgUXczasNpoMq4XaB67nbC0Fz9qw2Kl3deh3MC2B1Paht-NpkYPfv2e5e_d_gsmz_a68fGf06MVmGI41aoCbRVaqD29hlinkOu1Ob8AqZnzGA
openUrl	ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Structural+insights+and+cytotoxicity+evaluation+of+benz%5Be%5Dindole+pyrazolyl-substituted+amides&rft.jtitle=Molecular+diversity&rft.au=Ramle%2C+Abdul+Qaiyum&rft.au=Chan%2C+Nadia+Nabihah+Mohd+Yusof&rft.au=Ng%2C+Min+Phin&rft.au=Tan%2C+Chun+Hoe&rft.date=2024-06-01&rft.issn=1381-1991&rft.eissn=1573-501X&rft.volume=28&rft.issue=3&rft.spage=1363&rft.epage=1376&rft_id=info:doi/10.1007%2Fs11030-023-10662-2&rft.externalDBID=n%2Fa&rft.externalDocID=10_1007_s11030_023_10662_2
thumbnail_l	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1381-1991&client=summon
thumbnail_m	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1381-1991&client=summon
thumbnail_s	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1381-1991&client=summon