Synthesis, crystal structure and antiaromatase activity of 17-halo-16,17-seco-5-androstene derivatives

Penov-Gaši Katarina M.; Stojanović Srđan Z.; Sakač Marija N.; Đurendić Evgenija A.; Jovanović-Šanta Suzana S.; Stanković S.; Andrić Nebojša L.; Popsavin Mirjana M.

doi:10.2298/JSC0310707P

Journal of the Serbian Chemical Society (Jan 2003)

Synthesis, crystal structure and antiaromatase activity of 17-halo-16,17-seco-5-androstene derivatives

Penov-Gaši Katarina M.,
Stojanović Srđan Z.,
Sakač Marija N.,
Đurendić Evgenija A.,
Jovanović-Šanta Suzana S.,
Stanković S.,
Andrić Nebojša L.,
Popsavin Mirjana M.

Affiliations

Penov-Gaši Katarina M.: Department of Chemistry, Faculty of Science, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 3
Stojanović Srđan Z.: Department of Chemistry, Faculty of Science, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 3
Sakač Marija N.: Department of Chemistry, Faculty of Science, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 3
Đurendić Evgenija A.: Department of Chemistry, Faculty of Science, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 3
Jovanović-Šanta Suzana S.: Department of Physics, Faculty of Science, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 4
Stanković S.: nema
Andrić Nebojša L.: Department of Biology, Faculty of Science University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 2, Serbia and Montenegro
Popsavin Mirjana M.: Department of Chemistry, Faculty of Science, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 3

DOI: https://doi.org/10.2298/JSC0310707P
Journal volume & issue: Vol. 68, no. 10
pp. 707 – 714

Abstract

Read online

Starting from 3β-acetoxy-15-cyano-17-oxo-16,17-seco-5-androstene (2) and 3β-acetoxy- 15-cyano-17-hydroxy-17-methyl-16,17-seco-5-androstene (11), new 17-halo-derivatives (5–10 and 13) were obtained. The fluoro derivative 5 was obtained from 17-tosylate 4 in reaction with tetrabutylammonium fluoride. The structure of the 17-iodo-devitive 10 was unambiguously proved by the appropriate X-ray structural analysis. Compounds5–10, as well as 12 and 13 were tested for possible anti-aromatase activity, whereby only compound 9 with bromine as the C-17 substituent, induced 19.4 % inhibition of aromatase activity compared to the control.

Published in Journal of the Serbian Chemical Society

ISSN: 0352-5139 (Print); 1820-7421 (Online)
Publisher: Serbian Chemical Society
Country of publisher: Serbia
LCC subjects: Science: Chemistry
Website: http://www.shd-pub.org.rs/index.php/JSCS

About the journal

Abstract

Keywords