Structural Chemistry

, Volume 28, Issue 3, pp 567–576 | Cite as

Structural analysis and antitumor potential of novel 5,6-disubstituted-17a-homo-17-oxa-androstane derivatives

  • Ivana Kuzminac
  • Olivera R. Klisurić
  • Dušan Škorić
  • Dimitar Jakimov
  • Marija Sakač
Original Research

Abstract

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 24, 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.

Keywords

D-homoandrostane lactone Halogen derivatives NMR studies X-ray structural analysis Antiproliferative activity 

Notes

Acknowledgments

We thank the Ministry of Education, Science and Technological Development of the Republic of Serbia for financial support (Grant No. 172021).

Supplementary material

11224_2016_815_MOESM1_ESM.pdf (627 kb)
Supplementary material 1 (PDF 626 kb)

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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Department of Chemistry, Biochemistry and Environmental Protection, Faculty of SciencesUniversity of Novi SadNovi SadSerbia
  2. 2.Department of Physics, Faculty of SciencesUniversity of Novi SadNovi SadSerbia
  3. 3.Oncology Institute of VojvodinaSremska KamenicaSerbia

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