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":"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><p>A series of new 1<em>’H</em>-tetrazolo[1<em>’</em>,5<em>’</em>-<em>c</em>]-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<sup>-1</sup>. Only low cytotoxic activity against Hep-2, MCF-7, HepG2, and Hek293 cell lines was determined <em>in vitro</em> for the compounds obtained.</p></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 4","pages":"Pages 505-508"},"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}
引用次数: 0
Abstract
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.
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.
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