A minimalist approach to the stereoselective synthesis of 1R-alkoxygenipins
The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S-isomers; however, the challenge lies in the selective synthesis of these compounds. A streamlined and highly effective approach to achieve stereoselective 1R-alkyloxygenipins involved the use of a carefully bal...
Saved in:
Published in | Tetrahedron Vol. 161 |
---|---|
Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
17.07.2024
Elsevier |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S-isomers; however, the challenge lies in the selective synthesis of these compounds. A streamlined and highly effective approach to achieve stereoselective 1R-alkyloxygenipins involved the use of a carefully balanced mixture of Lewis acid catalytic reagents, specifically BF3·Et2O and H2O. This method emerged as the optimal choice after evaluating various synthetic routes, encompassing 1-OH and 10-OH substitutions, different Lewis acids, and their respective ratios as catalysts. The possible mechansim of the catalyst for genipin was investigated. Particularly, the method with non-strict conditions for the synthesis of 1R-alkoxygenipins was underscored by its operational simplicity, stability, and low energy consumption. This approach not only streamlined the synthetic process but also established a robust foundation for future bioactivity studies on 1R-alkyloxygenipins.
[Display omitted] |
---|---|
AbstractList | The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S-isomers; however, the challenge lies in the selective synthesis of these compounds. A streamlined and highly effective approach to achieve stereoselective 1R-alkyloxygenipins involved the use of a carefully balanced mixture of Lewis acid catalytic reagents, specifically BF3·Et2O and H2O. This method emerged as the optimal choice after evaluating various synthetic routes, encompassing 1-OH and 10-OH substitutions, different Lewis acids, and their respective ratios as catalysts. The possible mechansim of the catalyst for genipin was investigated. Particularly, the method with non-strict conditions for the synthesis of 1R-alkoxygenipins was underscored by its operational simplicity, stability, and low energy consumption. This approach not only streamlined the synthetic process but also established a robust foundation for future bioactivity studies on 1R-alkyloxygenipins.
[Display omitted] The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S -isomers; however, the challenge lies in the selective synthesis of these compounds. A streamlined and highly effective approach to achieve stereoselective 1R-alkyloxygenipins involved the use of a carefully balanced mixture of Lewis acid catalytic reagents, specifically BF 3 & sdot;Et 2 O and H 2 O. This method emerged as the optimal choice after evaluating various synthetic routes, encompassing 1 -OH and 10 -OH substitutions, different Lewis acids, and their respective ratios as catalysts. The possible mechansim of the catalyst for genipin was investigated. Particularly, the method with non -strict conditions for the synthesis of 1R-alkoxygenipins was underscored by its operational simplicity, stability, and low energy consumption. This approach not only streamlined the synthetic process but also established a robust foundation for future bioactivity studies on 1R-alkyloxygenipins. |
ArticleNumber | 134064 |
Author | Cai, Tian-Tian Yin-Liu Zhou, Jing Xie, Yun-Dong He, Yi-Fan Han, Chao-Jun Yan, Hao Liu, Ji-Ping Shi, Yong-Heng Meng, Fan-cui |
Author_xml | – sequence: 1 givenname: Yi-Fan orcidid: 0009-0008-9782-5987 surname: He fullname: He, Yi-Fan organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China – sequence: 2 givenname: Fan-cui surname: Meng fullname: Meng, Fan-cui organization: Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin, 300193, PR China – sequence: 3 givenname: Tian-Tian surname: Cai fullname: Cai, Tian-Tian organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China – sequence: 4 surname: Yin-Liu fullname: Yin-Liu organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China – sequence: 5 givenname: Yun-Dong surname: Xie fullname: Xie, Yun-Dong organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China – sequence: 6 givenname: Jing surname: Zhou fullname: Zhou, Jing organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China – sequence: 7 givenname: Hao surname: Yan fullname: Yan, Hao organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China – sequence: 8 givenname: Ji-Ping surname: Liu fullname: Liu, Ji-Ping organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China – sequence: 9 givenname: Chao-Jun surname: Han fullname: Han, Chao-Jun organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China – sequence: 10 givenname: Yong-Heng surname: Shi fullname: Shi, Yong-Heng email: yhshi@sntcm.edu.cn organization: College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, 712046, PR China |
BookMark | eNqNkctOwzAQRS1UJNrCB7DLHiWMHTsPsaoiXqISEoK15SQT6pLaUWwK-XtctR_AZl6aO9KZuyAzYw0Sck0hoUCz223i0ScMGE9oyiHjZ2ROecZjwWk2I3MADjEHBhdk4dwWAChl6Zy8rKKdNnqneu18pIZhtKrZRN5GfoOR8ziiddhj4_U-9JMJY6ddZLuIvsWq_7K_0ycaPWjjLsl5p3qHV6e8JB8P9-_VU7x-fXyuVusYaZr7EGsoiyyvSxChTFlJm1ZkqoZcFAJYywQ2mAnWAZSKlTlrOdSCtqlgrWpouiTF8e4P1rZzjUbToBzGQDFOMpAxXhY553CgrLRXXltT2W_jg_Tm_9KwfXfcxkCz1zjKk6LVY_iIbK2WFOTBALmVwQB5MEAeDUj_AD4Keio |
Cites_doi | 10.1002/ejoc.201800318 10.1021/acs.joc.2c02285 10.1016/S0040-4039(03)01401-1 10.1016/j.ejmech.2020.112508 10.1016/j.carres.2018.10.006 10.1016/j.fitote.2023.105616 10.1111/j.1471-4159.2011.07533.x 10.1021/jo400945j 10.1002/cmdc.201400051 10.1016/j.brainres.2016.05.011 10.1021/acs.jafc.7b05861 10.7503/cjcu20190140 10.1021/ja052548h 10.1039/c8ob00677f 10.3390/ijms17010117 10.1111/cbdd.13194 10.1016/j.ejmech.2020.113067 10.7503/cjcu20130284 10.1002/ejoc.200500607 10.1016/j.neuropharm.2014.09.019 10.1016/j.ejphar.2018.12.028 |
ContentType | Journal Article |
Copyright | 2024 Elsevier Ltd |
Copyright_xml | – notice: 2024 Elsevier Ltd |
DBID | 1KM BLEPL DTL |
DOI | 10.1016/j.tet.2024.134064 |
DatabaseName | Index Chemicus Web of Science Core Collection Science Citation Index Expanded |
DatabaseTitle | Web of Science |
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 | 001249874400001 S0040402024002448 |
GrantInformation_xml | – fundername: Natural Science Basic Research Program of Shaanxi grantid: 2024JC-YBMS-709 – fundername: Key Research Development Program of Shaanxi grantid: 2023-YBSF-278 – fundername: National Natural Science Foundation of China; National Natural Science Foundation of China (NSFC) grantid: 22201169 |
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 AAHBH AAIAV AAIKC AAIKJ AAKOC AALRI AAMNW AAOAW AAQFI AARLI AAXUO ABFNM ABGSF ABJNI ABMAC ABPPZ ABUDA 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 AKRWK ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ AXJTR BKOJK BLXMC CS3 DU5 EBS EFJIC EO8 EO9 EP2 EP3 F5P FDB FIRID FLBIZ FNPLU FYGXN G-Q GBLVA IHE J1W K-O KOM 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 AAXKI BLEPL DTL M2Z M41 |
ID | FETCH-LOGICAL-e137t-e1b09867b9051b03291cd56ab0758502d25ece652f009a2972d40b51d352dac13 |
IEDL.DBID | AIKHN |
ISICitedReferencesCount | 0 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=001249874400001 |
ISSN | 0040-4020 |
IngestDate | Wed Sep 18 07:31:22 EDT 2024 Fri Oct 18 20:05:30 EDT 2024 Tue Jun 18 08:51:24 EDT 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Language | English |
LinkModel | DirectLink |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-e137t-e1b09867b9051b03291cd56ab0758502d25ece652f009a2972d40b51d352dac13 |
ORCID | 0009-0008-9782-5987 |
PageCount | 8 |
ParticipantIDs | elsevier_sciencedirect_doi_10_1016_j_tet_2024_134064 webofscience_primary_001249874400001CitationCount webofscience_primary_001249874400001 |
PublicationCentury | 2000 |
PublicationDate | 2024-07-17 |
PublicationDateYYYYMMDD | 2024-07-17 |
PublicationDate_xml | – month: 07 year: 2024 text: 2024-07-17 day: 17 |
PublicationDecade | 2020 |
PublicationPlace | OXFORD |
PublicationPlace_xml | – name: OXFORD |
PublicationTitle | Tetrahedron |
PublicationTitleAbbrev | TETRAHEDRON |
PublicationYear | 2024 |
Publisher | Elsevier Ltd Elsevier |
Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
References | Koriyama, Takagi, Chiba (bib15) 2011; 119 Yao, Vu, Liu (bib18) 2019; 473 Zhang, Wang, Zhang (bib17) 2019; 7 Lv, Wang, Liu, Yan (bib2) 2015; 89 Ueno, Takeda, Iwasaki (bib5) 2001; 10 Mohamed, He, Lepage (bib24) 2018; 19 Kim, Yang, Park (bib25) 2005; 34 Huang, Wang, Li (bib12) 2019; 93 Hocek, Pohl, Klepetářová (bib22) 2005 Wang, Yang, Liao (bib7) 2014; 7 Jacox, Irikura, Thompson (bib29) 2000; 113 Yan, Tang, Gong (bib28) 2010; 24 Xia, Dong, Li (bib19) 2018; 6 Wang, Zhao, Zhang (bib16) 2016; 1 Suzuki, Yamazaki, Chiba (bib6) 2010; 2 Tran, Woerpel (bib27) 2013; 78 Zhang, Hao, Zhang (bib23) 2019; 9 Ding, Hou, Zhang (bib4) 2013; 2013 Lin, Rao, Li (bib11) 2021; 211 Zhao, Sun, Jiang (bib1) 2018; 845 Li, Bao, Wang (bib8) 2013; 12 S.H. Moon; H.J. Choi; S.J. Lee, et al., US006162826A. 2000.12.19. Luo, Li, Xu (bib10) 2023; 169 Jazouli, Guianvarc’h, Soufiaoui (bib21) 2003; 44 Su, Yang, Lou (bib3) 2016; 1644 Lei, Zhang, Qi (bib13) 2020; 205 Mukherji, Rotta, Sarmah (bib26) 2023; 1 Fang, Huang, Xia (bib14) 2018; 16 Carrière, Meunier, Tropper (bib20) 2000; 154 Li, ZW (WOS:000329081400013) 2013; 34 Koriyama, Y (WOS:000297948800008) 2011; 119 Yao, H (WOS:000456706500009) 2019; 473 Zhang, Z.Z. (001249874400001.17) 2019; 7 (001249874400001.9) 2000 Huang, WJ (WOS:000456793700002) 2019; 93 Kim, JH (WOS:000231605900058) 2005; 127 Lv, C (WOS:000347597600017) 2015; 89 Fang, JQ (WOS:000433441700026) 2018; 16 Lin, RT (WOS:000639375500025) 2021; 211 Xia, Q (WOS:000425474000006) 2018; 66 Ueno, K (WOS:000171855500021) 2001; 17 Mukherji, A (WOS:000903298300001) 2023; 88 Lei, SW (WOS:000578986400003) 2020; 205 Luo, LP (WOS:001048870600001) 2023; 169 Suzuki, H (WOS:000274007200006) 2010; 58 Yan, H (WOS:000286352700010) 2010; 68 Hocek, M (WOS:000233144000004) 2005; 2005 Tran, VT (WOS:000321605900024) 2013; 78 Zhao, BS (WOS:000456771100008) 2019; 845 Zhang, YY (WOS:000492677600016) 2019; 40 Wang, RK (WOS:000374583800111) 2016; 17 Wang, RK (WOS:000338991100008) 2014; 9 Su, CH (WOS:000379105300012) 2016; 1644 Jacox, ME (WOS:000089524400013) 2000; 113 Ding, Y. (001249874400001.4) 2013; 2013 Mohamed, S (WOS:000433497300008) 2018; 2018 Carrière, D (WOS:000086257200003) 2000; 154 Jazouli, M (WOS:000184220600010) 2003; 44 |
References_xml | – volume: 1 start-page: 117 year: 2016 ident: bib16 publication-title: Int. J. Mol. Sci. contributor: fullname: Zhang – volume: 2 start-page: 168 year: 2010 end-page: 171 ident: bib6 publication-title: Chem. Pharm. Bull. contributor: fullname: Chiba – volume: 2013 year: 2013 ident: bib4 publication-title: Evid. base Compl. Alternative Med. contributor: fullname: Zhang – volume: 119 start-page: 1232 year: 2011 end-page: 1242 ident: bib15 publication-title: J. Neurochem. contributor: fullname: Chiba – volume: 169 year: 2023 ident: bib10 publication-title: Fitoterapia contributor: fullname: Xu – volume: 16 start-page: 3026 year: 2018 end-page: 3037 ident: bib14 publication-title: Org. Biomol. Chem. contributor: fullname: Xia – volume: 78 start-page: 6609 year: 2013 end-page: 6621 ident: bib27 publication-title: Org. Chem. contributor: fullname: Woerpel – volume: 7 start-page: 1397 year: 2014 end-page: 1403 ident: bib7 publication-title: ChemMedChem contributor: fullname: Liao – volume: 24 start-page: 2559 year: 2010 end-page: 2563 ident: bib28 publication-title: Acta. Chim. Sinica. contributor: fullname: Gong – volume: 12 start-page: 2752 year: 2013 end-page: 2758 ident: bib8 publication-title: Chem. J. Chin. Univ. contributor: fullname: Wang – volume: 113 start-page: 5705 year: 2000 end-page: 5715 ident: bib29 publication-title: J. Chem. Phys. contributor: fullname: Thompson – volume: 6 start-page: 1341 year: 2018 end-page: 1348 ident: bib19 publication-title: J. Agric. Food Chem. contributor: fullname: Li – volume: 44 start-page: 5807 year: 2003 end-page: 5810 ident: bib21 publication-title: Tetrahedron Lett. contributor: fullname: Soufiaoui – volume: 34 start-page: 12090 year: 2005 end-page: 12097 ident: bib25 publication-title: J. Am. Chem. Soc. contributor: fullname: Park – volume: 19 start-page: 2214 year: 2018 end-page: 2227 ident: bib24 publication-title: Eur. J. Org Chem. contributor: fullname: Lepage – volume: 89 start-page: 175 year: 2015 end-page: 184 ident: bib2 publication-title: Neuropharmacology contributor: fullname: Yan – volume: 10 start-page: 1237 year: 2001 end-page: 1239 ident: bib5 publication-title: Anal. Sci. contributor: fullname: Iwasaki – volume: 7 start-page: 1180 year: 2019 end-page: 1186 ident: bib17 publication-title: Med. Chem. Commun. contributor: fullname: Zhang – volume: 473 start-page: 72 year: 2019 end-page: 81 ident: bib18 publication-title: Carbohydr. Res. contributor: fullname: Liu – volume: 9 start-page: 1904 year: 2019 end-page: 1910 ident: bib23 publication-title: Chem. J. Chin. Univ. contributor: fullname: Zhang – volume: 211 year: 2021 ident: bib11 publication-title: Eur. J. Med. Chem. contributor: fullname: Li – start-page: 4525 year: 2005 end-page: 4528 ident: bib22 publication-title: Eur. J. Org. Chem. contributor: fullname: Klepetářová – volume: 1 start-page: 245 year: 2023 end-page: 260 ident: bib26 publication-title: J. Org. Chem. contributor: fullname: Sarmah – volume: 205 year: 2020 ident: bib13 publication-title: Eur. J. Med. Chem. contributor: fullname: Qi – volume: 154 start-page: 9 year: 2000 end-page: 22 ident: bib20 publication-title: J. Mol. Catal. A Chem. contributor: fullname: Tropper – volume: 93 start-page: 110 year: 2019 end-page: 122 ident: bib12 publication-title: Chem. Biol. Drug Des. contributor: fullname: Li – volume: 1644 start-page: 98 year: 2016 end-page: 106 ident: bib3 publication-title: Brain Res. contributor: fullname: Lou – volume: 845 start-page: 56 year: 2018 end-page: 64 ident: bib1 publication-title: Eur. J. Pharmacol. contributor: fullname: Jiang – volume: 2018 start-page: 2214 year: 2018 ident: WOS:000433497300008 article-title: Glycosylations of Simple Acceptors with 2-O-Acyl l-Idose or l-Iduronic Acid Donors Reveal Only a Minor Role for Neighbouring-Group Participation publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201800318 contributor: fullname: Mohamed, S – volume: 88 start-page: 245 year: 2023 ident: WOS:000903298300001 article-title: Influence of Various Silyl Protecting Groups on Stereoselective 2-Deoxyrhamnosylation publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.2c02285 contributor: fullname: Mukherji, A – volume: 58 start-page: 168 year: 2010 ident: WOS:000274007200006 article-title: Neuritogenic Activities of 1-Alkyloxygenipins publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: Suzuki, H – volume: 44 start-page: 5807 year: 2003 ident: WOS:000184220600010 article-title: A short and efficient synthesis of 2′-deoxybenzo- and pyridoimidazole C-nucleosides publication-title: TETRAHEDRON LETTERS doi: 10.1016/S0040-4039(03)01401-1 contributor: fullname: Jazouli, M – volume: 205 start-page: ARTN 112508 year: 2020 ident: WOS:000578986400003 article-title: Synthesis and biological evaluation of geniposide derivatives as potent and selective PTPlB inhibitors publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2020.112508 contributor: fullname: Lei, SW – volume: 17 start-page: 1237 year: 2001 ident: WOS:000171855500021 article-title: Simultaneous estimation of geniposide and genipin in mouse plasma using high-performance liquid chromatography publication-title: ANALYTICAL SCIENCES contributor: fullname: Ueno, K – volume: 473 start-page: 72 year: 2019 ident: WOS:000456706500009 article-title: Recent advances in reagent-controlled stereoselective/stereospecific glycosylation publication-title: CARBOHYDRATE RESEARCH doi: 10.1016/j.carres.2018.10.006 contributor: fullname: Yao, H – volume: 169 start-page: ARTN 105616 year: 2023 ident: WOS:001048870600001 article-title: Synthesis and neuroprotective effects of new genipin derivatives against glutamate-induced oxidative damage publication-title: FITOTERAPIA doi: 10.1016/j.fitote.2023.105616 contributor: fullname: Luo, LP – volume: 119 start-page: 1232 year: 2011 ident: WOS:000297948800008 article-title: Neuritogenic activity of a genipin derivative in retinal ganglion cells is mediated by retinoic acid receptor β expression through nitric oxide/S-nitrosylation signaling publication-title: JOURNAL OF NEUROCHEMISTRY doi: 10.1111/j.1471-4159.2011.07533.x contributor: fullname: Koriyama, Y – volume: 78 start-page: 6609 year: 2013 ident: WOS:000321605900024 article-title: Nucleophilic Addition to Silyl-Protected Five-Membered Ring Oxocarbenium Ions Governed by Stereoelectronic Effects publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo400945j contributor: fullname: Tran, VT – volume: 7 start-page: 1180 year: 2019 ident: 001249874400001.17 publication-title: Med. Chem. Commun. contributor: fullname: Zhang, Z.Z. – volume: 9 start-page: 1397 year: 2014 ident: WOS:000338991100008 article-title: Stereoselective Reduction of 1-O-Isopropyloxygenipin Enhances Its Neuroprotective Activity in Neuronal Cells from Apoptosis Induced by Sodium Nitroprusside publication-title: CHEMMEDCHEM doi: 10.1002/cmdc.201400051 contributor: fullname: Wang, RK – volume: 1644 start-page: 98 year: 2016 ident: WOS:000379105300012 article-title: Geniposide reduces α-synuclein by blocking microRNA-21/lysosome-associated membrane protein 2A interaction in Parkinson disease models publication-title: BRAIN RESEARCH doi: 10.1016/j.brainres.2016.05.011 contributor: fullname: Su, CH – volume: 66 start-page: 1341 year: 2018 ident: WOS:000425474000006 article-title: Discovery of Glycosylated Genipin Derivatives as Novel Antiviral, Insecticidal, and Fungicidal Agents publication-title: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY doi: 10.1021/acs.jafc.7b05861 contributor: fullname: Xia, Q – volume: 40 start-page: 1904 year: 2019 ident: WOS:000492677600016 article-title: β-Stereoselectivity of Glucuronic Acid Analogues Mediated by 2-Cyanobenzyl Group publication-title: CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE doi: 10.7503/cjcu20190140 contributor: fullname: Zhang, YY – volume: 127 start-page: 12090 year: 2005 ident: WOS:000231605900058 article-title: A general strategy for stereoselective glycosylations publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja052548h contributor: fullname: Kim, JH – volume: 16 start-page: 3026 year: 2018 ident: WOS:000433441700026 article-title: Design and synthesis of novel monoterpenoid indole alkaloid-like analogues and their antitumour activities in vitro publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c8ob00677f contributor: fullname: Fang, JQ – volume: 17 start-page: ARTN 117 year: 2016 ident: WOS:000374583800111 article-title: Genipin Derivatives Protect RGC-5 from Sodium Nitroprusside-Induced Nitrosative Stress publication-title: INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES doi: 10.3390/ijms17010117 contributor: fullname: Wang, RK – volume: 93 start-page: 110 year: 2019 ident: WOS:000456793700002 article-title: Design, synthesis, and evaluation of genipin derivatives for the treatment of Alzheimer's Disease publication-title: CHEMICAL BIOLOGY & DRUG DESIGN doi: 10.1111/cbdd.13194 contributor: fullname: Huang, WJ – volume: 211 start-page: ARTN 113067 year: 2021 ident: WOS:000639375500025 article-title: Conjugation of tacrine with genipin derivative not only enhances effects on AChE but also leads to autophagy against Alzheimer's disease publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2020.113067 contributor: fullname: Lin, RT – volume: 113 start-page: 5705 year: 2000 ident: WOS:000089524400013 article-title: The reaction of BF3 with H2O:: Infrared spectrum of BF2OH trapped in solid neon publication-title: JOURNAL OF CHEMICAL PHYSICS contributor: fullname: Jacox, ME – year: 2000 ident: 001249874400001.9 – volume: 34 start-page: 2752 year: 2013 ident: WOS:000329081400013 article-title: Synthesis, Characterization and Antidiabetic Activities of Novel Genipin Derivatives publication-title: CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE doi: 10.7503/cjcu20130284 contributor: fullname: Li, ZW – volume: 2005 start-page: 4525 year: 2005 ident: WOS:000233144000004 article-title: A new modular and practical methodology for the synthesis of 4-or 3-substituted phenyl C-nucleosides publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200500607 contributor: fullname: Hocek, M – volume: 89 start-page: 175 year: 2015 ident: WOS:000347597600017 article-title: Multi-faced neuroprotective effects of geniposide depending on the RAGE-mediated signaling in an Alzheimer mouse model publication-title: NEUROPHARMACOLOGY doi: 10.1016/j.neuropharm.2014.09.019 contributor: fullname: Lv, C – volume: 845 start-page: 56 year: 2019 ident: WOS:000456771100008 article-title: Genipin protects against cerebral ischemia-reperfusion injury by regulating the UCP2-SIRT3 signaling pathway publication-title: EUROPEAN JOURNAL OF PHARMACOLOGY doi: 10.1016/j.ejphar.2018.12.028 contributor: fullname: Zhao, BS – volume: 2013 year: 2013 ident: 001249874400001.4 publication-title: Evid. base Compl. Alternative Med. contributor: fullname: Ding, Y. – volume: 68 start-page: 2559 year: 2010 ident: WOS:000286352700010 article-title: Theoretical Study on the Reaction of Boron Trifluoride with Water by Density Functional Theory publication-title: ACTA CHIMICA SINICA contributor: fullname: Yan, H – volume: 154 start-page: 9 year: 2000 ident: WOS:000086257200003 article-title: Phase transfer catalysis toward the synthesis of O-, S-, Se- and C-glycosides publication-title: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL contributor: fullname: Carrière, D |
SSID | ssj0001123 |
Score | 2.500104 |
Snippet | The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S-isomers; however, the challenge lies in the selective synthesis of... The 1R-alkoxygenipins exhibit significantly enhanced bioactivity in comparison to their S -isomers; however, the challenge lies in the selective synthesis of... |
Source | Web of Science |
SourceID | webofscience elsevier |
SourceType | Enrichment Source Index Database Publisher |
SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | A minimalist approach to the stereoselective synthesis of 1R-alkoxygenipins |
URI | https://dx.doi.org/10.1016/j.tet.2024.134064 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001249874400001 |
Volume | 161 |
WOS | 001249874400001 |
WOSCitedRecordID | wos001249874400001 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3JasMwEB2yHNpL6UrTJeiQqxMvkpdjMA1pAzmUBnIzliVDusShdqG59Ns74yU00EPpxWAhg5gZZrHevAEYCJ1IjdZrKF-kBhcyNeLEkgZXgZv4gaDfhIS2mLvTBX9YimULwqYXhmCVte-vfHrpreuVUS3N0Wa1oh5fblL1QyhIDFJ-G7oYjjjvQHd8P5vOdw4ZU4odeI4-aC43S5hXoQlRafOh5WBs43sx6ZdQVIadyTEc1fkiG1dHOoGWXp_CQdiMaTuD2ZgRPcgbERkWrKEIZ0XGMLVjRIOgs7wcdoN-jeXbNS7nq5xlKbMejfj1JfvcohGVI6zPYTG5ewqnRj0hwdCW4xX4lGbgu54kli1pOnZgJUq4sTSpDDBtZaMutCvsFFOp2A48W3FTCkth2qVQJ84FdNbZWl8C05pLzYUnReBzW2HRHPDUT5LAlDKVjuwBbwQT7SkoQt8bNVix5wjlGZE8o0qePRj8FGK0qTg0CEqHhR9x75f3Cz2w_rItrHnLqV-_uPrfia7hkN6MkhzzBjrF-4e-xcSikH1oD7-sfm0-37HvzHY |
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/eLvHCXMwnV07T8MwED6VMpQF8RTl6aFr2jzsPMYqoiq0dECt1C2KE0cqj6QiQaILv527PHhIDIglg-PBOp_uvrM_fwfQEyqSCr1Xi12RaFzIRAsjQ2o89uzI9QQdExLbYmaPF_x2KZYt8Ju3MESrrGN_FdPLaF2PDGprDtarFb3x5TpVP8SCxCTlbsE2oQHidfXfv3geCCg-qXM0vbnaLElehSI-pcn7hoWZjf_ISL8kojLpjPZgt0aLbFgtaB9aKj2Ajt80aTuEyZCROMgzyRgWrBEIZ0XGENgxEkFQWV62usGoxvJNisP5KmdZwox7LXx6zN426EJlA-sjWIyu5_5Yq_sjaMqwnAK_Uvdc25GksSV1y_SMKBZ2KHUqAnQzNnEnlC3MBIFUaHqOGXNdCiNG0BXjjljH0E6zVJ0AU4pLxYUjhedyM8aS2eOJG0WeLmUiLdkF3hgm-LE9AUbeoGGKPQRoz4DsGVT27ELvuxGDdaWgQUQ6LPtIeb-8XeiC8Zdpfq1aTq_1i9P_regKOuP53TSY3swmZ7BDf7RSJvMc2sXLq7pAiFHIy9KFPgB72M1L |
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=A+minimalist+approach+to+the+stereoselective+synthesis+of+1R-alkoxygenipins&rft.jtitle=Tetrahedron&rft.au=He%2C+Yi-Fan&rft.au=Meng%2C+Fan-cui&rft.au=Cai%2C+Tian-Tian&rft.au=Yin-Liu&rft.date=2024-07-17&rft.pub=Elsevier+Ltd&rft.issn=0040-4020&rft.eissn=1464-5416&rft.volume=161&rft_id=info:doi/10.1016%2Fj.tet.2024.134064&rft.externalDocID=S0040402024002448 |
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 |