新型四唑并[1',5'-c]融合 3-氮杂-A-类固醇的合成、结构和细胞毒性

IF 1.8 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Mendeleev Communications Pub Date : 2024-07-01 DOI:10.1016/j.mencom.2024.06.011

Evgenii I. Rodionov , Alina A. Rodionova , Alla D. Zorina , Olesya V. Khoroshilova , Vitalii V. Suslonov , Elizaveta V. Lider , Yuliya A. Golubeva , Lyubov S. Klyushova , Yuri B. Porozov , Nikolay N. Kuzmich , Rostislav E. Trifonov

{"title":"新型四唑并[1',5'-c]融合 3-氮杂-A-类固醇的合成、结构和细胞毒性","authors":"Evgenii I. Rodionov , Alina A. Rodionova , Alla D. Zorina , Olesya V. Khoroshilova , Vitalii V. Suslonov , Elizaveta V. Lider , Yuliya A. Golubeva , Lyubov S. Klyushova , Yuri B. Porozov , Nikolay N. Kuzmich , Rostislav E. Trifonov","doi":"10.1016/j.mencom.2024.06.011","DOIUrl":null,"url":null,"abstract":"<div>A series of new 1’H-tetrazolo[1’,5’-c]-fused 3-aza-A- homosteroids were synthesized by azidation of progesterone, testosterone and hydrocortisone acetate in the presence of silicon tetrachloride. According to NMR spectroscopy and X-ray analysis, two double bond positional isomers (double bond in ring A or in ring B) are formed in various ratios; according to quantum chemical calculations, their energies are close within 0.4 kcal mol-1. Only low cytotoxic activity against Hep-2, MCF-7, HepG2, and Hek293 cell lines was determined in vitro for the compounds obtained.</div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":null,"pages":null},"PeriodicalIF":1.8000,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids\",\"authors\":\"Evgenii I. Rodionov , Alina A. Rodionova , Alla D. Zorina , Olesya V. Khoroshilova , Vitalii V. Suslonov , Elizaveta V. Lider , Yuliya A. Golubeva , Lyubov S. Klyushova , Yuri B. Porozov , Nikolay N. Kuzmich , Rostislav E. Trifonov\",\"doi\":\"10.1016/j.mencom.2024.06.011\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>A series of new 1’H-tetrazolo[1’,5’-c]-fused 3-aza-A- homosteroids were synthesized by azidation of progesterone, testosterone and hydrocortisone acetate in the presence of silicon tetrachloride. According to NMR spectroscopy and X-ray analysis, two double bond positional isomers (double bond in ring A or in ring B) are formed in various ratios; according to quantum chemical calculations, their energies are close within 0.4 kcal mol-1. Only low cytotoxic activity against Hep-2, MCF-7, HepG2, and Hek293 cell lines was determined in vitro for the compounds obtained.</div>\",\"PeriodicalId\":18542,\"journal\":{\"name\":\"Mendeleev Communications\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-07-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Mendeleev Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0959943624001883\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Mendeleev Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0959943624001883","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

在四氯化硅存在下，通过对黄体酮、睾酮和醋酸氢化可的松进行叠氮化反应，合成了一系列新的 1'H-四唑并[1',5'-c]-融合 3-aza-A- 同甾类化合物。根据核磁共振光谱和 X 射线分析，以不同比例形成了两种双键位置异构体（双键位于 A 环或 B 环）；根据量子化学计算，它们的能量接近 0.4 kcal mol-1。所获得的化合物在体外对 Hep-2、MCF-7、HepG2 和 Hek293 细胞株的细胞毒性较低。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

摘要图片

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids

A series of new 1’H-tetrazolo[1’,5’-c]-fused 3-aza-A- homosteroids were synthesized by azidation of progesterone, testosterone and hydrocortisone acetate in the presence of silicon tetrachloride. According to NMR spectroscopy and X-ray analysis, two double bond positional isomers (double bond in ring A or in ring B) are formed in various ratios; according to quantum chemical calculations, their energies are close within 0.4 kcal mol^-1. Only low cytotoxic activity against Hep-2, MCF-7, HepG2, and Hek293 cell lines was determined in vitro for the compounds obtained.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Mendeleev Communications 化学-化学综合

CiteScore

3.00

自引率

21.10%

发文量

226

审稿时长

4-8 weeks

期刊介绍： Mendeleev Communications is the journal of the Russian Academy of Sciences, launched jointly by the Academy of Sciences of the USSR and the Royal Society of Chemistry (United Kingdom) in 1991. Starting from 1st January 2007, Elsevier is the new publishing partner of Mendeleev Communications. Mendeleev Communications publishes short communications in chemistry. The journal primarily features papers from the Russian Federation and the other states of the former USSR. However, it also includes papers by authors from other parts of the world. Mendeleev Communications is not a translated journal, but instead is published directly in English. The International Editorial Board is composed of eminent scientists who provide advice on refereeing policy.

期刊最新文献

Editorial Board Symmetry relationships between hybrid lead halide perovskite-derived phases: vacancy ordering as a key classification factor Fluorene-based π-conjugated polymers for OLEDs: advances, opportunities, and challenges Electrochemical oxidation of furans into 2,5-dimethoxy-2,5-dihydrofurans N-Vinylation of lactams with calcium carbide water system