Indole phytoalexins-derived bis-indoles: Design, synthesis and in vitro antiproliferative evaluation
Natural indole phytoalexins isolated from Brassicaceae plants have been identified as promising anticancer leads. Herein, we designed and synthesized six novel bis-indole series as indole phytoalexins analogues. Our design is based on replacing the SCH3 group in the natural leads by the peripheral i...
Saved in:
Published in | Tetrahedron Vol. 143; pp. 133573 - 133587 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
21.08.2023
Elsevier |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | Natural indole phytoalexins isolated from Brassicaceae plants have been identified as promising anticancer leads. Herein, we designed and synthesized six novel bis-indole series as indole phytoalexins analogues. Our design is based on replacing the SCH3 group in the natural leads by the peripheral indole ring. The key first series — bis indole thioureas, prepared from starting [1-(tert-butoxycarbonyl)indol-3-yl]methyl isothiocyanate and 1-substituted (indol-3-yl)methylamine derivatives, were further transformed by oxidative spirocyclization with chromium oxide, bromospirocyclization protocol or methyl bromoacetate. The in vitro antiproliferation/cytotoxicity assays against human cancer cell lines demonstrated the bis-indole spirocompounds cis-28b and cis-31b were the most active compounds exhibiting a similar extent of effects against HeLa and HCT116 cells (a range of IC50 values between 7.4 and 10.8 μM). At the same time, their activities were higher or comparable to cisplatin. Furthermore, compounds cis-28b and cis-31b displayed good selectivity indexes (SIs) spanning in the range 9.3–13.5. Collective, these results show that reported bis-indoles are promising candidate for cervix and colon cancer treatment and suitable for further investigations.
[Display omitted]
•Syntheses of novel bis-indole analogues of natural indole phytoalexins were accomplished.•The used strategy relied on oxidative cyclization, bromospirocyclization and methyl bromoacetate-mediated cyclization.•Bis-indole spirocompounds were active against HeLa, HCT116 cells and at the same time had a good selectivity and safety profile. |
---|---|
AbstractList | Natural indole phytoalexins isolated from Brassicaceae plants have been identified as promising anticancer leads. Herein, we designed and synthesized six novel bis-indole series as indole phytoalexins analogues. Our design is based on replacing the SCH3 group in the natural leads by the peripheral indole ring. The key first series — bis indole thioureas, prepared from starting [1-(tert-butoxycarbonyl)indol-3-yl]methyl isothiocyanate and 1-substituted (indol-3-yl)methylamine derivatives, were further transformed by oxidative spirocyclization with chromium oxide, bromospirocyclization protocol or methyl bromoacetate. The in vitro antiproliferation/cytotoxicity assays against human cancer cell lines demonstrated the bis-indole spirocompounds cis-28b and cis-31b were the most active compounds exhibiting a similar extent of effects against HeLa and HCT116 cells (a range of IC50 values between 7.4 and 10.8 μM). At the same time, their activities were higher or comparable to cisplatin. Furthermore, compounds cis-28b and cis-31b displayed good selectivity indexes (SIs) spanning in the range 9.3–13.5. Collective, these results show that reported bis-indoles are promising candidate for cervix and colon cancer treatment and suitable for further investigations.
[Display omitted]
•Syntheses of novel bis-indole analogues of natural indole phytoalexins were accomplished.•The used strategy relied on oxidative cyclization, bromospirocyclization and methyl bromoacetate-mediated cyclization.•Bis-indole spirocompounds were active against HeLa, HCT116 cells and at the same time had a good selectivity and safety profile. Natural indole phytoalexins isolated from Brassicaceae plants have been identified as promising anticancer leads. Herein, we designed and synthesized six novel bis-indole series as indole phytoalexins analogues. Our design is based on replacing the SCH3 group in the natural leads by the peripheral indole ring. The key first series - bis indole thioureas, prepared from starting [1-(tert-butoxycarbonyl)indol-3-yl]methyl isothiocyanate and 1substituted (indol-3-yl)methylamine derivatives, were further transformed by oxidative spirocyclization with chromium oxide, bromospirocyclization protocol or methyl bromoacetate. The in vitro antiproliferation/cytotoxicity assays against human cancer cell lines demonstrated the bis-indole spirocompounds cis-28b and cis-31b were the most active compounds exhibiting a similar extent of effects against HeLa and HCT116 cells (a range of IC50 values between 7.4 and 10.8 & mu;M). At the same time, their activities were higher or comparable to cisplatin. Furthermore, compounds cis-28b and cis-31b displayed good selectivity indexes (SIs) spanning in the range 9.3-13.5. Collective, these results show that reported bis-indoles are promising candidate for cervix and colon cancer treatment and suitable for further investigations. |
ArticleNumber | 133573 |
Author | Mojžiš, Ján Budovská, Mariana Michalková, Radka |
Author_xml | – sequence: 1 givenname: Mariana surname: Budovska fullname: Budovska, Mariana email: mariana.budovska@upjs.sk organization: Pavol Jozefsafarik Univ Kosice, Inst Chem, Fac Sci, Dept Organ Chem, Moyzesova 11, Kosice 04001, Slovakia – sequence: 2 givenname: Radka surname: Michalkova fullname: Michalkova, Radka organization: Pavol Jozefsafarik Univ Kosice, Inst Chem, Fac Sci, Dept Organ Chem, Moyzesova 11, Kosice 04001, Slovakia – sequence: 3 givenname: Jan surname: Mojzis fullname: Mojzis, Jan organization: Pavol Jozefsafarik Univ Kosice, Inst Chem, Fac Sci, Dept Organ Chem, Moyzesova 11, Kosice 04001, Slovakia |
BookMark | eNqNkM1OAyEURompiW31AdzNXqdeYJi2ujL1r0kTN7omzHCxNCM0gNW-vbQ1Lo2r-93wHQJnQHrOOyTknMKIAq2vVqOEacSA8RHlXIz5EenTqq5KUdG6R_oAFZQVMDghgxhXAEAp432i5077Dov1cpu86vDLulhqDHaDumhsLO3-PF4Xdxjtm7ss4talZc6xUE4X1hUbm4LPS7Lr4DtrMKiU8QI3qvvI0btTcmxUF_HsZw7J68P9y-ypXDw_zme3i7Jl03EqWTNBrWjD2wYYCq4nAtEIWlfaIB9PAQwyBKqoHhuB3AiOjWjMtKrVBCjyIaGHe9vgYwxo5DrYdxW2koLcaZIrmTXJnSZ50JSZyYH5xMab2Fp0Lf5yWROI3GQV7JTNbNp_aOY_XMroxf_R3L45tDEb2FgM8ofQNmCbpPb2j2d-A1JplX8 |
CitedBy_id | crossref_primary_10_1016_j_cclet_2023_109005 crossref_primary_10_3390_molecules29081773 |
Cites_doi | 10.3390/molecules28010251 10.3390/cells10020332 10.1039/c1np00020a 10.1007/s00706-019-02528-x 10.1016/j.tet.2017.09.033 10.1515/chempap-2015-0230 10.1016/j.bmc.2013.08.020 10.1016/j.tiv.2014.04.002 10.1038/sj.onc.1210939 10.1016/B978-0-12-398282-7.00001-1 10.3390/molecules190810877 10.3390/molecules21121626 10.1002/ptr.6233 10.1002/ptr.5010 10.1016/j.jfluchem.2018.09.011 10.3892/ijo.2011.1246 10.1016/j.bmc.2009.03.064 10.1159/000152027 10.1039/b515331j 10.1007/s00706-020-02693-4 10.3390/plants12030611 10.3748/wjg.v23.i24.4341 10.1002/ardp.202000092 10.1016/S0040-4039(02)02452-8 10.1016/0022-1759(83)90303-4 |
ContentType | Journal Article |
Copyright | 2023 Elsevier Ltd |
Copyright_xml | – notice: 2023 Elsevier Ltd |
DBID | 1KM BLEPL BNZSX DTL AAYXX CITATION |
DOI | 10.1016/j.tet.2023.133573 |
DatabaseName | Index Chemicus Web of Science Core Collection Web of Science - Science Citation Index Expanded - 2023 Science Citation Index Expanded CrossRef |
DatabaseTitle | Web of Science CrossRef |
DatabaseTitleList | Web of Science |
Database_xml | – sequence: 1 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1464-5416 |
ExternalDocumentID | 10_1016_j_tet_2023_133573 001051332400001 S0040402023003757 |
GrantInformation_xml | – fundername: Grant Agency of Ministry of the Education, Science, Research and Sport of the Slovak Republic grantid: VEGA 1/0539/21; VEGA 1/0347/23 – fundername: Operational Programme Integrated Infrastructure - ERDF; European Union (EU) grantid: ITMS2014 + : 313011V455 – fundername: Slovak Research and Development Agency grantid: APVV-16-0446 |
GroupedDBID | --- --K --M -DZ -ET -~X .~1 0R~ 123 1B1 1~. 1~5 4.4 457 4G. 5RE 5VS 7-5 71M 8P~ 9JM 9JN AABNK AACTN AAEDT AAEDW AAIAV AAIKC AAIKJ AAKOC AALRI AAMNW AAOAW AAQFI AARLI AATCM AAXUO ABFNM ABGSF ABJNI ABMAC ABPPZ ABUDA ABYKQ ABZDS ACDAQ ACGFS ACNCT ACRLP ADBBV ADECG ADEZE ADUVX AEBSH AEHWI AEKER AENEX AFKWA AFTJW AFXIZ AFZHZ AGUBO AGYEJ AHHHB AIEXJ AIKHN AITUG AJOXV AJSZI ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ AXJTR BKOJK BLXMC CS3 DOVZS DU5 EBS EFJIC EFLBG EO8 EO9 EP2 EP3 F5P FDB FIRID FLBIZ FNPLU FYGXN G-Q GBLVA IHE J1W K-O KOM M2Z M41 MO0 N9A O-L O9- OAUVE OGGZJ OZT P-8 P-9 P2P PC. Q38 RNS ROL RPZ SCC SDF SDG SDP SES SEW SOC SPC SPCBC SSK SSP SSU T5K TN5 TWZ WH7 XPP XSW YK3 YR2 ZMT ~G- 1KM 53G AAHBH AAXKI AKRWK BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED .GJ 186 1RT 29Q 6TJ AAQXK AAYJJ AAYXX ABEFU ABXDB ACBNA ACKIV ACNNM ADMUD ADVLN AFFNX AFJKZ AGHFR AGRDE ASPBG AVWKF AZFZN CITATION EJD FEDTE FGOYB G8K HMS HVGLF HZ~ MVM NEJ OHT PVJ R2- RIG SCB UQL WUQ XOL ZCG ZKB |
ID | FETCH-LOGICAL-c297t-2b8eda1b3cb02e53d85eef5164dfe37900fe2e01a1d7f5e3f53eb5bf946a801e3 |
IEDL.DBID | AIKHN |
ISICitedReferencesCount | 2 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=001051332400001 |
ISSN | 0040-4020 |
IngestDate | Thu Sep 26 18:18:05 EDT 2024 Wed Sep 18 08:09:39 EDT 2024 Fri Oct 18 19:37:13 EDT 2024 Fri Feb 23 02:34:13 EST 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Keywords | Cyclization reactions Bis-indoles Antiproliferative/cytotoxic activity Indole phytoalexins Antiproliferative APOPTOSIS ANALOGS BRASSININ SPIROBRASSININ ANTICANCER ACTIVITY INHIBITION cytotoxic activity 1-METHOXYSPIROBRASSINOL METHYL-ETHER DERIVATIVES |
Language | English |
LinkModel | DirectLink |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-c297t-2b8eda1b3cb02e53d85eef5164dfe37900fe2e01a1d7f5e3f53eb5bf946a801e3 |
ORCID | 0000-0003-0544-1289 |
PageCount | 15 |
ParticipantIDs | webofscience_primary_001051332400001 webofscience_primary_001051332400001CitationCount crossref_primary_10_1016_j_tet_2023_133573 elsevier_sciencedirect_doi_10_1016_j_tet_2023_133573 |
PublicationCentury | 2000 |
PublicationDate | 2023-08-21 |
PublicationDateYYYYMMDD | 2023-08-21 |
PublicationDate_xml | – month: 08 year: 2023 text: 2023-08-21 day: 21 |
PublicationDecade | 2020 |
PublicationPlace | OXFORD |
PublicationPlace_xml | – name: OXFORD |
PublicationTitle | Tetrahedron |
PublicationTitleAbbrev | TETRAHEDRON |
PublicationYear | 2023 |
Publisher | Elsevier Ltd Elsevier |
Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
References | Bakar-Ates, Ozkan (bib7) 2019; 33 Kim, Park, Kim, Nam, Shim, Kim, Ahn, Choi, Ahn (bib6) 2014; 28 Pedras, Yaya, Glawischnig (bib1) 2011; 28 Budovská, Selešová, Tischlerová, Michalková, Mojžiš (bib16) 2020; 151 Budovská, Tischlerová, Mojžiš, Harvanová, Kozlov, Gondová, Tomášková (bib13) 2017; 73 Budovska, Michalkova, Kello, Vaskova, Mojzis (bib17) 2023; 28 Kello, Drutovic, Chripkova, Pilatova, Budovska, Kulikova, Urdzik, Mojzis (bib5) 2014; 19 Kello, Goga, Kotorova, Sebova, Frenak, Tkacikova, Mojzis (bib26) 2023; 12 Chripkova, Drutovic, Pilatova, Mikes, Budovska, Vaskova, Broggini, Mirossay, Mojzis (bib4) 2014; 28 Očenášová, Kutschy, Gonda, Pilátová, Gönciová, Mojžiš, Pazdera (bib21) 2016; 70 Hong, Ham, Song, Song, Lim (bib8) 2021; 10 Avendano, Menendez (bib19) 2023 Chripkova, Zigo, Mojzis (bib12) 2016; 21 Pedras, Suchý, Ahiahonu (bib22) 2006; 4 Gribble (bib20) 2012 Zhang, Hu (bib18) 2020; 353 Kutschy, Suchý, Monde, Harada, Marušková, Čurillová, Dzurilla, Miklošová, Mezencev, Mojžiš (bib24) 2002; 43 Mosmann (bib25) 1983; 65 Izutani, Yogosawa, Sowa, Sakai (bib3) 2012; 40 Budovská, Baláž, Mezencev, Tischlerová, Zigová, Mojžiš (bib15) 2018; 216 Budovská, Pilatová, Varinská, Mojžiš, Mezencev (bib11) 2013; 21 Kutschy, Salayova, Curillova, Kozar, Mezencev, Mojzis, Pilatova, Balentova, Pazdera, Sabol, Zburova (bib10) 2009; 17 Budovska, Tischlerova, Mojzis, Kozlov, Gondova (bib23) 2020; 151 Mezencev, Kutschy, Salayova, Curillova, Mojzis, Pilatova, McDonald (bib9) 2008; 54 Banerjee, Duhadaway, Gaspari, Sutanto-Ward, Munn, Mellor, Malachowski, Prendergast, Muller (bib2) 2008; 27 Tischlerova, Kello, Budovska, Mojzis (bib14) 2017; 23 Budovská, M (WOS:000325164500038) 2013; 21 Tischlerova, V (WOS:000405228300004) 2017; 23 Mezencev, R (WOS:000259876500008) 2008; 54 Izutani, Y (WOS:000300118200024) 2012; 40 Pedras, MSC (WOS:000292975700003) 2011; 28 Kutschy, P (WOS:000179684700002) 2002; 43 Kim, SM (WOS:000332988100012) 2014; 28 Chripkova, M (WOS:000338616800022) 2014; 28 Budovská, M (WOS:000587082700002) 2020; 151 Gribble, GW (WOS:000311027600002) 2012; 71 MOSMANN, T (WOS:A1983RW94600004) 1983; 65 Zhang, Y (WOS:000536638900001) 2020; 353 Budovská, M (WOS:000451938800004) 2018; 216 Kutschy, P (WOS:000265683800022) 2009; 17 Kello, M (WOS:000341502600011) 2014; 19 Bakar-Ates, F (WOS:000457745900016) 2019; 33 Chripkova, M (WOS:000392140100020) 2016; 21 Pedras, MSC (WOS:000235778600023) 2006; 4 Ocenásová, L (WOS:000376512000013) 2016; 70 Hong, T (WOS:000622396500001) 2021; 10 Kello, M (WOS:000930439900001) 2023; 12 Budovská, M (WOS:000513228600007) 2020; 151 Budovska, M (WOS:000910225400001) 2023; 28 Avendano, C. (001051332400001.19) 2023; third Budovská, M (WOS:000413798200014) 2017; 73 Banerjee, T (WOS:000255502500006) 2008; 27 Kello (10.1016/j.tet.2023.133573_bib5) 2014; 19 Kutschy (10.1016/j.tet.2023.133573_bib24) 2002; 43 Budovská (10.1016/j.tet.2023.133573_bib13) 2017; 73 Mosmann (10.1016/j.tet.2023.133573_bib25) 1983; 65 Chripkova (10.1016/j.tet.2023.133573_bib12) 2016; 21 Kello (10.1016/j.tet.2023.133573_bib26) 2023; 12 Budovska (10.1016/j.tet.2023.133573_bib17) 2023; 28 Mezencev (10.1016/j.tet.2023.133573_bib9) 2008; 54 Banerjee (10.1016/j.tet.2023.133573_bib2) 2008; 27 Budovská (10.1016/j.tet.2023.133573_bib15) 2018; 216 Budovska (10.1016/j.tet.2023.133573_bib23) 2020; 151 Avendano (10.1016/j.tet.2023.133573_bib19) 2023 Pedras (10.1016/j.tet.2023.133573_bib22) 2006; 4 Bakar-Ates (10.1016/j.tet.2023.133573_bib7) 2019; 33 Budovská (10.1016/j.tet.2023.133573_bib11) 2013; 21 Gribble (10.1016/j.tet.2023.133573_bib20) 2012 Chripkova (10.1016/j.tet.2023.133573_bib4) 2014; 28 Zhang (10.1016/j.tet.2023.133573_bib18) 2020; 353 Izutani (10.1016/j.tet.2023.133573_bib3) 2012; 40 Očenášová (10.1016/j.tet.2023.133573_bib21) 2016; 70 Budovská (10.1016/j.tet.2023.133573_bib16) 2020; 151 Pedras (10.1016/j.tet.2023.133573_bib1) 2011; 28 Hong (10.1016/j.tet.2023.133573_bib8) 2021; 10 Kim (10.1016/j.tet.2023.133573_bib6) 2014; 28 Tischlerova (10.1016/j.tet.2023.133573_bib14) 2017; 23 Kutschy (10.1016/j.tet.2023.133573_bib10) 2009; 17 |
References_xml | – volume: 17 start-page: 3698 year: 2009 end-page: 3712 ident: bib10 article-title: 2-(substituted phenyl)aminoanalogs of 1-methoxyspirobrassinol methyl ether: synthesis and anti-cancer activit publication-title: Bioorg. Med. Chem. contributor: fullname: Zburova – volume: 216 start-page: 24 year: 2018 end-page: 32 ident: bib15 article-title: Design, synthesis and anticancer activity of trifluoromethylphenylamino substituted spiroindoles publication-title: J. Fluor. Chem. contributor: fullname: Mojžiš – volume: 28 start-page: 251 year: 2023 ident: bib17 article-title: Design, synthesis and antiproliferative evaluation of bis-indole derivatives with a phenyl linker: focus on autophagy publication-title: Molecules contributor: fullname: Mojzis – volume: 23 start-page: 4341 year: 2017 end-page: 4353 ident: bib14 article-title: Indole phytoalexin derivatives induce mitochondrial-mediated apoptosis in human colorectal carcinoma cells publication-title: World J. Gastroenterol. contributor: fullname: Mojzis – volume: 151 start-page: 63 year: 2020 end-page: 77 ident: bib23 article-title: An alternative approach to the synthesis of anticancer molecule spirobrassinin and its 2′-amino analogues publication-title: Monatsh. Chem. contributor: fullname: Gondova – volume: 27 start-page: 2851 year: 2008 end-page: 2857 ident: bib2 article-title: A key in vivo antitumor mechanism of action of natural product-based brassinins is inhibition of indoleamine 2,3-dioxygenase publication-title: Oncogene contributor: fullname: Muller – volume: 12 start-page: 611 year: 2023 ident: bib26 article-title: Screening evaluation of antiproliferative, antimicrobial and antioxidant activity of lichen extracts and secondary metabolites in vitro publication-title: Plants contributor: fullname: Mojzis – volume: 54 start-page: 372 year: 2008 end-page: 378 ident: bib9 article-title: Anticancer properties of 2-piperidyl analogues of the natural indole phytoalexin 1-methoxyspirobrassinol publication-title: Chemotherapy contributor: fullname: McDonald – start-page: 1 year: 2012 end-page: 165 ident: bib20 publication-title: Occurrence of Halogenated Alkaloids. The Alkaloids contributor: fullname: Gribble – volume: 40 start-page: 816 year: 2012 end-page: 824 ident: bib3 article-title: Brassinin induces G1 phase arrest through increase of p21 and p27 by inhibition of the phosphatidylinositol 3-kinase signaling pathway in human colon cancer cells publication-title: Int. J. Oncol. contributor: fullname: Sakai – volume: 10 start-page: 332 year: 2021 ident: bib8 article-title: Brassinin inhibits proliferation in human liver cancer cells via mitochondrial dysfunction publication-title: Cells contributor: fullname: Lim – volume: 28 start-page: 423 year: 2014 end-page: 431 ident: bib6 article-title: Brassinin induces apoptosis in PC-3 human prostate cancer cells through the suppression of PI3K/Akt/mTOR/S6K1 signaling cascades publication-title: Phytother Res. contributor: fullname: Ahn – volume: 33 start-page: 397 year: 2019 end-page: 402 ident: bib7 article-title: The combined treatment of brassinin and imatinib synergistically downregulated the expression of MMP-9 in SW480 colon cancer cells publication-title: Phytother. Res. contributor: fullname: Ozkan – volume: 73 start-page: 6356 year: 2017 end-page: 6371 ident: bib13 article-title: 2′-Aminoanalogues of the cruciferous phytoalexins spirobrassinin, 1-methoxyspirobrassinin and 1-methoxyspirobrassinol methyl ether: synthesis and anticancer properties publication-title: Tetrahedron contributor: fullname: Tomášková – volume: 65 start-page: 55 year: 1983 end-page: 63 ident: bib25 article-title: Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays publication-title: J. Immunol. Methods contributor: fullname: Mosmann – volume: 70 start-page: 635 year: 2016 end-page: 648 ident: bib21 article-title: Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins publication-title: Chem. Pap. contributor: fullname: Pazdera – volume: 19 start-page: 10877 year: 2014 end-page: 10897 ident: bib5 article-title: ROS-dependent anti-proliferative effect of brassinin derivative homobrassinin in human colorectal cancer Caco2 cells publication-title: Molecules contributor: fullname: Mojzis – volume: 4 start-page: 691 year: 2006 end-page: 701 ident: bib22 article-title: Unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum publication-title: Org. Biomol. Chem. contributor: fullname: Ahiahonu – volume: 353 year: 2020 ident: bib18 article-title: Anticancer activity of bisindole alkaloids derived from natural sources and synthetic bisindole hybrids publication-title: Arch. Pharm. contributor: fullname: Hu – volume: 151 start-page: 1737 year: 2020 end-page: 1758 ident: bib16 article-title: Design, synthesis, and biological evaluation of novel 5-bromo derivatives of indole phytoalexins Monatsh publication-title: Chem contributor: fullname: Mojžiš – volume: 21 start-page: 6623 year: 2013 end-page: 6633 ident: bib11 article-title: The synthesis and anti-cancer activity of analogs of the indole phytoalexins brassinin, 1-methoxyspirobrassinol methyl ether and cyclobrassinin publication-title: Bioorg. Med. Chem. contributor: fullname: Mezencev – volume: 43 start-page: 9489 year: 2002 end-page: 9492 ident: bib24 article-title: Spirocyclization strategy toward indole phytoalexins. The first synthesis of (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, and (±)-1-methoxyspirobrassinol methyl ether publication-title: Tetrahedron Lett. contributor: fullname: Mojžiš – volume: 28 start-page: 1381 year: 2011 end-page: 1405 ident: bib1 article-title: The phytoalexins from cultivated and wild crucifers: chemistry and biology publication-title: Nat. Prod. Rep. contributor: fullname: Glawischnig – volume: 28 start-page: 909 year: 2014 end-page: 915 ident: bib4 article-title: Brassinin and its derivatives as potential anticancer agents publication-title: Toxicol. Vitro contributor: fullname: Mojzis – volume: 21 start-page: 1626 year: 2016 end-page: 1640 ident: bib12 article-title: Antiproliferative effect of indole phytoalexins publication-title: Molecules contributor: fullname: Mojzis – year: 2023 ident: bib19 article-title: Medicinal Chemistry of Anticancer Drugs contributor: fullname: Menendez – volume: 28 start-page: ARTN 251 year: 2023 ident: WOS:000910225400001 article-title: Design, Synthesis and Antiproliferative Evaluation of Bis-Indole Derivatives with a Phenyl Linker: Focus on Autophagy publication-title: MOLECULES doi: 10.3390/molecules28010251 contributor: fullname: Budovska, M – volume: 10 start-page: ARTN 332 year: 2021 ident: WOS:000622396500001 article-title: Brassinin Inhibits Proliferation in Human Liver Cancer Cells via Mitochondrial Dysfunction publication-title: CELLS doi: 10.3390/cells10020332 contributor: fullname: Hong, T – volume: 65 start-page: 55 year: 1983 ident: WOS:A1983RW94600004 article-title: RAPID COLORIMETRIC ASSAY FOR CELLULAR GROWTH AND SURVIVAL - APPLICATION TO PROLIFERATION AND CYTO-TOXICITY ASSAYS publication-title: JOURNAL OF IMMUNOLOGICAL METHODS contributor: fullname: MOSMANN, T – volume: third year: 2023 ident: 001051332400001.19 publication-title: Medicinal Chemistry of Anticancer Drugs contributor: fullname: Avendano, C. – volume: 28 start-page: 1381 year: 2011 ident: WOS:000292975700003 article-title: The phytoalexins from cultivated and wild crucifers: Chemistry and biology publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/c1np00020a contributor: fullname: Pedras, MSC – volume: 151 start-page: 63 year: 2020 ident: WOS:000513228600007 article-title: An alternative approach to the synthesis of anticancer molecule spirobrassinin and its 2′-amino analogues publication-title: MONATSHEFTE FUR CHEMIE doi: 10.1007/s00706-019-02528-x contributor: fullname: Budovská, M – volume: 73 start-page: 6356 year: 2017 ident: WOS:000413798200014 article-title: 2′-Aminoanalogues of the cruciferous phytoalexins spirobrassinin, 1-methoxyspirobrassinin and 1-methoxyspirobrassinol methyl ether: Synthesis and anticancer properties publication-title: TETRAHEDRON doi: 10.1016/j.tet.2017.09.033 contributor: fullname: Budovská, M – volume: 70 start-page: 635 year: 2016 ident: WOS:000376512000013 article-title: Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins publication-title: CHEMICAL PAPERS doi: 10.1515/chempap-2015-0230 contributor: fullname: Ocenásová, L – volume: 21 start-page: 6623 year: 2013 ident: WOS:000325164500038 article-title: The synthesis and anticancer activity of analogs of the indole phytoalexins brassinin, 1-methoxyspirobrassinol methyl ether and cyclobrassinin publication-title: BIOORGANIC & MEDICINAL CHEMISTRY doi: 10.1016/j.bmc.2013.08.020 contributor: fullname: Budovská, M – volume: 28 start-page: 909 year: 2014 ident: WOS:000338616800022 article-title: Brassinin and its derivatives as potential anticancer agents publication-title: TOXICOLOGY IN VITRO doi: 10.1016/j.tiv.2014.04.002 contributor: fullname: Chripkova, M – volume: 43 start-page: 9489 year: 2002 ident: WOS:000179684700002 article-title: Spirocyclization strategy toward indole phytoalexins. The first synthesis of (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, and (±)-1-methoxyspirobrassinol methyl ether publication-title: TETRAHEDRON LETTERS contributor: fullname: Kutschy, P – volume: 27 start-page: 2851 year: 2008 ident: WOS:000255502500006 article-title: A key in vivo antitumor mechanism of action of natural product-based brassinins is inhibition of indoleamine 2,3-dioxygenase publication-title: ONCOGENE doi: 10.1038/sj.onc.1210939 contributor: fullname: Banerjee, T – volume: 71 start-page: 1 year: 2012 ident: WOS:000311027600002 article-title: Occurrence of Halogenated Alkaloids publication-title: ALKALOIDS: CHEMISTRY AND BIOLOGY, VOL 71 doi: 10.1016/B978-0-12-398282-7.00001-1 contributor: fullname: Gribble, GW – volume: 19 start-page: 10877 year: 2014 ident: WOS:000341502600011 article-title: ROS-Dependent Antiproliferative Effect of Brassinin Derivative Homobrassinin in Human Colorectal Cancer Caco2 Cells publication-title: MOLECULES doi: 10.3390/molecules190810877 contributor: fullname: Kello, M – volume: 21 start-page: ARTN 1626 year: 2016 ident: WOS:000392140100020 article-title: Antiproliferative Effect of Indole Phytoalexins publication-title: MOLECULES doi: 10.3390/molecules21121626 contributor: fullname: Chripkova, M – volume: 33 start-page: 397 year: 2019 ident: WOS:000457745900016 article-title: The combined treatment of brassinin and imatinib synergistically downregulated the expression of MMP-9 in SW480 colon cancer cells publication-title: PHYTOTHERAPY RESEARCH doi: 10.1002/ptr.6233 contributor: fullname: Bakar-Ates, F – volume: 28 start-page: 423 year: 2014 ident: WOS:000332988100012 article-title: Brassinin Induces Apoptosis in PC-3 Human Prostate Cancer Cells through the Suppression of PI3K/Akt/mTOR/S6K1 Signaling Cascades publication-title: PHYTOTHERAPY RESEARCH doi: 10.1002/ptr.5010 contributor: fullname: Kim, SM – volume: 216 start-page: 24 year: 2018 ident: WOS:000451938800004 article-title: Design, synthesis and anticancer activity of trifluoromethylphenylamino substituted spiroindoles publication-title: JOURNAL OF FLUORINE CHEMISTRY doi: 10.1016/j.jfluchem.2018.09.011 contributor: fullname: Budovská, M – volume: 40 start-page: 816 year: 2012 ident: WOS:000300118200024 article-title: Brassinin induces G1 phase arrest through increase of p21 and p27 by inhibition of the phosphatidylinositol 3-kinase signaling pathway in human colon cancer cells publication-title: INTERNATIONAL JOURNAL OF ONCOLOGY doi: 10.3892/ijo.2011.1246 contributor: fullname: Izutani, Y – volume: 17 start-page: 3698 year: 2009 ident: WOS:000265683800022 article-title: 2-(Substituted phenyl)amino analogs of 1-methoxyspirobrassinol methyl ether: Synthesis and anticancer activity publication-title: BIOORGANIC & MEDICINAL CHEMISTRY doi: 10.1016/j.bmc.2009.03.064 contributor: fullname: Kutschy, P – volume: 54 start-page: 372 year: 2008 ident: WOS:000259876500008 article-title: Anticancer properties of 2-piperidyl analogues of the natural indole phytoalexin 1-methoxyspirobrassinol publication-title: CHEMOTHERAPY doi: 10.1159/000152027 contributor: fullname: Mezencev, R – volume: 4 start-page: 691 year: 2006 ident: WOS:000235778600023 article-title: Unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/b515331j contributor: fullname: Pedras, MSC – volume: 151 start-page: 1737 year: 2020 ident: WOS:000587082700002 article-title: Design, synthesis, and biological evaluation of novel 5-bromo derivatives of indole phytoalexins publication-title: MONATSHEFTE FUR CHEMIE doi: 10.1007/s00706-020-02693-4 contributor: fullname: Budovská, M – volume: 12 start-page: ARTN 611 year: 2023 ident: WOS:000930439900001 article-title: Screening Evaluation of Antiproliferative, Antimicrobial and Antioxidant Activity of Lichen Extracts and Secondary Metabolites In Vitro publication-title: PLANTS-BASEL doi: 10.3390/plants12030611 contributor: fullname: Kello, M – volume: 23 start-page: 4341 year: 2017 ident: WOS:000405228300004 article-title: Indole phytoalexin derivatives induce mitochondrial-mediated apoptosis in human colorectal carcinoma cells publication-title: WORLD JOURNAL OF GASTROENTEROLOGY doi: 10.3748/wjg.v23.i24.4341 contributor: fullname: Tischlerova, V – volume: 353 start-page: ARTN e2000092 year: 2020 ident: WOS:000536638900001 article-title: Anticancer activity of bisindole alkaloids derived from natural sources and synthetic bisindole hybrids publication-title: ARCHIV DER PHARMAZIE doi: 10.1002/ardp.202000092 contributor: fullname: Zhang, Y – volume: 33 start-page: 397 year: 2019 ident: 10.1016/j.tet.2023.133573_bib7 article-title: The combined treatment of brassinin and imatinib synergistically downregulated the expression of MMP-9 in SW480 colon cancer cells publication-title: Phytother. Res. doi: 10.1002/ptr.6233 contributor: fullname: Bakar-Ates – volume: 23 start-page: 4341 year: 2017 ident: 10.1016/j.tet.2023.133573_bib14 article-title: Indole phytoalexin derivatives induce mitochondrial-mediated apoptosis in human colorectal carcinoma cells publication-title: World J. Gastroenterol. doi: 10.3748/wjg.v23.i24.4341 contributor: fullname: Tischlerova – volume: 27 start-page: 2851 year: 2008 ident: 10.1016/j.tet.2023.133573_bib2 article-title: A key in vivo antitumor mechanism of action of natural product-based brassinins is inhibition of indoleamine 2,3-dioxygenase publication-title: Oncogene doi: 10.1038/sj.onc.1210939 contributor: fullname: Banerjee – volume: 43 start-page: 9489 year: 2002 ident: 10.1016/j.tet.2023.133573_bib24 article-title: Spirocyclization strategy toward indole phytoalexins. The first synthesis of (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, and (±)-1-methoxyspirobrassinol methyl ether publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(02)02452-8 contributor: fullname: Kutschy – volume: 28 start-page: 423 year: 2014 ident: 10.1016/j.tet.2023.133573_bib6 article-title: Brassinin induces apoptosis in PC-3 human prostate cancer cells through the suppression of PI3K/Akt/mTOR/S6K1 signaling cascades publication-title: Phytother Res. doi: 10.1002/ptr.5010 contributor: fullname: Kim – volume: 151 start-page: 63 year: 2020 ident: 10.1016/j.tet.2023.133573_bib23 article-title: An alternative approach to the synthesis of anticancer molecule spirobrassinin and its 2′-amino analogues publication-title: Monatsh. Chem. doi: 10.1007/s00706-019-02528-x contributor: fullname: Budovska – volume: 65 start-page: 55 year: 1983 ident: 10.1016/j.tet.2023.133573_bib25 article-title: Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays publication-title: J. Immunol. Methods doi: 10.1016/0022-1759(83)90303-4 contributor: fullname: Mosmann – volume: 21 start-page: 6623 year: 2013 ident: 10.1016/j.tet.2023.133573_bib11 article-title: The synthesis and anti-cancer activity of analogs of the indole phytoalexins brassinin, 1-methoxyspirobrassinol methyl ether and cyclobrassinin publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2013.08.020 contributor: fullname: Budovská – volume: 151 start-page: 1737 year: 2020 ident: 10.1016/j.tet.2023.133573_bib16 article-title: Design, synthesis, and biological evaluation of novel 5-bromo derivatives of indole phytoalexins Monatsh publication-title: Chem contributor: fullname: Budovská – volume: 216 start-page: 24 year: 2018 ident: 10.1016/j.tet.2023.133573_bib15 article-title: Design, synthesis and anticancer activity of trifluoromethylphenylamino substituted spiroindoles publication-title: J. Fluor. Chem. doi: 10.1016/j.jfluchem.2018.09.011 contributor: fullname: Budovská – volume: 40 start-page: 816 year: 2012 ident: 10.1016/j.tet.2023.133573_bib3 article-title: Brassinin induces G1 phase arrest through increase of p21 and p27 by inhibition of the phosphatidylinositol 3-kinase signaling pathway in human colon cancer cells publication-title: Int. J. Oncol. contributor: fullname: Izutani – volume: 10 start-page: 332 year: 2021 ident: 10.1016/j.tet.2023.133573_bib8 article-title: Brassinin inhibits proliferation in human liver cancer cells via mitochondrial dysfunction publication-title: Cells doi: 10.3390/cells10020332 contributor: fullname: Hong – volume: 17 start-page: 3698 year: 2009 ident: 10.1016/j.tet.2023.133573_bib10 article-title: 2-(substituted phenyl)aminoanalogs of 1-methoxyspirobrassinol methyl ether: synthesis and anti-cancer activit publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2009.03.064 contributor: fullname: Kutschy – volume: 28 start-page: 1381 year: 2011 ident: 10.1016/j.tet.2023.133573_bib1 article-title: The phytoalexins from cultivated and wild crucifers: chemistry and biology publication-title: Nat. Prod. Rep. doi: 10.1039/c1np00020a contributor: fullname: Pedras – volume: 28 start-page: 909 year: 2014 ident: 10.1016/j.tet.2023.133573_bib4 article-title: Brassinin and its derivatives as potential anticancer agents publication-title: Toxicol. Vitro doi: 10.1016/j.tiv.2014.04.002 contributor: fullname: Chripkova – volume: 70 start-page: 635 year: 2016 ident: 10.1016/j.tet.2023.133573_bib21 article-title: Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins publication-title: Chem. Pap. contributor: fullname: Očenášová – volume: 19 start-page: 10877 year: 2014 ident: 10.1016/j.tet.2023.133573_bib5 article-title: ROS-dependent anti-proliferative effect of brassinin derivative homobrassinin in human colorectal cancer Caco2 cells publication-title: Molecules doi: 10.3390/molecules190810877 contributor: fullname: Kello – volume: 12 start-page: 611 year: 2023 ident: 10.1016/j.tet.2023.133573_bib26 article-title: Screening evaluation of antiproliferative, antimicrobial and antioxidant activity of lichen extracts and secondary metabolites in vitro publication-title: Plants doi: 10.3390/plants12030611 contributor: fullname: Kello – volume: 4 start-page: 691 year: 2006 ident: 10.1016/j.tet.2023.133573_bib22 article-title: Unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum publication-title: Org. Biomol. Chem. doi: 10.1039/b515331j contributor: fullname: Pedras – volume: 54 start-page: 372 year: 2008 ident: 10.1016/j.tet.2023.133573_bib9 article-title: Anticancer properties of 2-piperidyl analogues of the natural indole phytoalexin 1-methoxyspirobrassinol publication-title: Chemotherapy doi: 10.1159/000152027 contributor: fullname: Mezencev – volume: 21 start-page: 1626 year: 2016 ident: 10.1016/j.tet.2023.133573_bib12 article-title: Antiproliferative effect of indole phytoalexins publication-title: Molecules doi: 10.3390/molecules21121626 contributor: fullname: Chripkova – volume: 28 start-page: 251 year: 2023 ident: 10.1016/j.tet.2023.133573_bib17 article-title: Design, synthesis and antiproliferative evaluation of bis-indole derivatives with a phenyl linker: focus on autophagy publication-title: Molecules doi: 10.3390/molecules28010251 contributor: fullname: Budovska – volume: 353 year: 2020 ident: 10.1016/j.tet.2023.133573_bib18 article-title: Anticancer activity of bisindole alkaloids derived from natural sources and synthetic bisindole hybrids publication-title: Arch. Pharm. doi: 10.1002/ardp.202000092 contributor: fullname: Zhang – start-page: 1 year: 2012 ident: 10.1016/j.tet.2023.133573_bib20 contributor: fullname: Gribble – year: 2023 ident: 10.1016/j.tet.2023.133573_bib19 contributor: fullname: Avendano – volume: 73 start-page: 6356 year: 2017 ident: 10.1016/j.tet.2023.133573_bib13 article-title: 2′-Aminoanalogues of the cruciferous phytoalexins spirobrassinin, 1-methoxyspirobrassinin and 1-methoxyspirobrassinol methyl ether: synthesis and anticancer properties publication-title: Tetrahedron doi: 10.1016/j.tet.2017.09.033 contributor: fullname: Budovská |
SSID | ssj0001123 |
Score | 2.4855936 |
Snippet | Natural indole phytoalexins isolated from Brassicaceae plants have been identified as promising anticancer leads. Herein, we designed and synthesized six novel... |
Source | Web of Science |
SourceID | crossref webofscience elsevier |
SourceType | Aggregation Database Enrichment Source Index Database Publisher |
StartPage | 133573 |
SubjectTerms | Antiproliferative/cytotoxic activity Bis-indoles Chemistry Chemistry, Organic Cyclization reactions Indole phytoalexins Physical Sciences Science & Technology |
Title | Indole phytoalexins-derived bis-indoles: Design, synthesis and in vitro antiproliferative evaluation |
URI | https://dx.doi.org/10.1016/j.tet.2023.133573 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001051332400001 |
Volume | 143 |
WOS | 001051332400001 |
WOSCitedRecordID | wos001051332400001 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LT9wwEB4ty4FeUAtUXSjIB06ohiS2ScINLUW7IDgViVtkxxMpPWRXJCBx6W_vTB5bKgGqeosTW7HG1jzsb74BOIwjFadJlEvvCiO1DRNptUGZeEw0J346z0cDN7enszt9dW_uRzAdcmEYVtnr_k6nt9q6f3PSS_NkWZac46sDjn7IieZCrvEarJM50noM6-fz69ntSiGTS7ECz_GA4XKzhXk1yIjKSB1TsGZi9ZZ5esUqtRbo8iNs9q6jOO9m9wlGWG3BxnSo2LYNfl4xP5MgyTULy0yXVS09bbEn9MKVtSzb7_WZuGhxG99E_VyRA1iXtbCVF2UlnsrmYUGNplxyOZ8CO2Jw8YcUfAfuLr__mM5kX0VB5lEaNzJyCXobOpW7IEKjfGIQC0Nhki-QFioICowwCG3o48KgKoxCZ1yR6lNL5gvVZxhXiwq_gGCiH4rPdI6p0bmzzhqfpylftSVeJcEEjgbhZcuOLCMbUGQ_M5J0xpLOOklPQA_izf5a8YyU-XvDDl8uxeo_balP6sKYWHqeQPgv3aY9EToTADS7_zejPfjALT5ojsKvMG4eHnGfPJXGHcDa8a_woN-PvwHRjef7 |
link.rule.ids | 315,786,790,4521,24144,27955,27956,45618,45712 |
linkProvider | Elsevier |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LS8QwEB50PehFfOL6zMGTGG2bZNt6k1VZnycFbyVpplAP3cVWwYu_3UwfPkBFvDVNSsOXMI_kmxmA3TAQYRwFKbcmU1xqP-JaKuSRxUhS4KexdDRwfTMY3cmLe3U_BcMuFoZola3sb2R6La3bN4ctmoeTPKcYX-mR9-OMaCrkGk7DDFkDxOs6eP3geTiD4p06R8O7q82a5FUh8SkDceBcNRWKn5TTNzqp1j9nCzDfGo7suJnbIkxhsQSzw65e2zLY84KyMzGHWzXWlOeyKLl1G-wZLTN5yfO6vzxiJzVrY5-VL4Uz_8q8ZLqwLC_Yc149jl2jyidUzCfDJi04-0gJvgJ3Z6e3wxFvayjwNIjDigcmQqt9I1LjBaiEjRRippyTZDN0y-R5GQbo-dq3YaZQZEqgUSaL5UA75YViFXrFuMA1YJTmx3lnMsVYydRoo5VN45gu2iIrIq8Pex14yaRJlZF0HLKHxCGdENJJg3QfZAdv8mW9EyfKf_ts9_NSvP-nLvTphhAj1j33wf_LsGGbBp3C_6v1_81oB2ZHt9dXydX5zeUGzFEPHTkH_ib0qscn3HI2S2W26z35BuCt6NA |
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=Indole+phytoalexins-derived+bis-indoles%3A+Design%2C+synthesis+and+in+vitro+antiproliferative+evaluation&rft.jtitle=Tetrahedron&rft.au=Budovska%2C+Mariana&rft.au=Michalkova%2C+Radka&rft.au=Mojzis%2C+Jan&rft.date=2023-08-21&rft.pub=Elsevier&rft.issn=0040-4020&rft.eissn=1464-5416&rft.volume=143&rft_id=info:doi/10.1016%2Fj.tet.2023.133573&rft.externalDBID=n%2Fa&rft.externalDocID=001051332400001 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4020&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4020&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4020&client=summon |