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https://open.uns.ac.rs/handle/123456789/17258
Title: | Structural analysis and antitumor potential of novel 5,6-disubstituted-17a-homo-17-oxa-androstane derivatives | Authors: | Kuzminac Ivana Klisurić Olivera Škorić Dušan Jakimov D. Sakac Marija |
Issue Date: | 2017 | Journal: | Structural Chemistry | Abstract: | © 2016, Springer Science+Business Media New York. Starting from 3β-acetoxy-17a-homo-17-oxa-androst-5-en-16-one (1) and in the reaction with N-bromoacetamide (NBA) and perchloric acid, the 5α-bromo-6β-hydroxy (2), 5β,6β-epoxy (3) and 5α,6β-dibromo (4) derivatives were obtained. The structure of compounds 2–4, particularly stereochemistry at C5 and C6, is established by detailed NMR and X-ray analysis. The in vitro antiproliferative activity of newly synthesized compounds 2–4 against six human tumor cell lines was evaluated. All three compounds showed a significant toxicity toward hormone-independent breast adenocarcinoma MDA-MB-231 and cervical carcinoma cells HeLa, while dibromo derivative 4 was active toward five human cancer cell lines. These new 5,6-disubstituted-D-homolactone steroidal compounds have also displayed selectivity toward cancerous cell lines against inactivity found for noncancerous control cell line. This selectivity was not found for control compound, well-known chemotherapy drug cisplatin. | URI: | https://open.uns.ac.rs/handle/123456789/17258 | ISSN: | 1040-0400 1572-9001 |
DOI: | 10.1007/s11224-016-0815-9 |
Appears in Collections: | PMF Publikacije/Publications |
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