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New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities
dc.creator | Krstić, Natalija M. | |
dc.creator | Bjelaković, Mira S. | |
dc.creator | Pavlović, Vladimir D. | |
dc.creator | Robeyns, Koen | |
dc.creator | Juranić, Zorica D. | |
dc.creator | Matić, Ivana Z. | |
dc.creator | Novaković, Irena T. | |
dc.creator | Sladić, Dušan | |
dc.date.accessioned | 2018-11-22T00:21:02Z | |
dc.date.available | 2018-11-22T00:21:02Z | |
dc.date.issued | 2012 | |
dc.identifier.issn | 0039-128X | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/1282 | |
dc.description.abstract | The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity. (C) 2012 Elsevier Inc. All rights reserved. | en |
dc.publisher | Elsevier Science Inc, New York | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172055/RS// | |
dc.rights | restrictedAccess | |
dc.source | Steroids | |
dc.subject | Phosphorus heterocycle | en |
dc.subject | 17 alpha-Hydroxyprogesterone | en |
dc.subject | Lawesson's reagent | en |
dc.subject | X-ray analysis | en |
dc.subject | 17-Spiro-androstene derivatives | en |
dc.subject | Biological activity | en |
dc.title | New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Сладић, Душан; Матиц, Ивана; Робеyнс, Коен; Павловиц, Владимир Д.; Крстиц, Наталија М.; Бјелаковиц, Мира С.; Јураниц, Зорица Д.; Новаковиц, Ирена; | |
dc.citation.volume | 77 | |
dc.citation.issue | 5 | |
dc.citation.spage | 558 | |
dc.citation.epage | 565 | |
dc.identifier.wos | 000303084000028 | |
dc.identifier.doi | 10.1016/j.steroids.2012.01.021 | |
dc.citation.other | 77(5): 558-565 | |
dc.citation.rank | M22 | |
dc.identifier.pmid | 22342468 | |
dc.type.version | publishedVersion | en |
dc.identifier.scopus | 2-s2.0-84858335299 |