[17(20)E]- and [17(20)Z]-pregna-5,17(20)-dien-21-oylamides. Facile synthesis and primary evaluation for cancer cells proliferation

Sergey V Stulov; Maria G Zavialova; Arif R Mehtiev; Roman A Novikov; Yaroslav V Tkachev; Vladimir P Timofeev; Alexander Yu Misharin

doi:10.1016/j.bmcl.2010.07.075

[17(20)E]- and [17(20)Z]-pregna-5,17(20)-dien-21-oylamides. Facile synthesis and primary evaluation for cancer cells proliferation

Bioorg Med Chem Lett. 2010 Sep 15;20(18):5495-8. doi: 10.1016/j.bmcl.2010.07.075. Epub 2010 Jul 21.

Authors

Sergey V Stulov¹, Maria G Zavialova, Arif R Mehtiev, Roman A Novikov, Yaroslav V Tkachev, Vladimir P Timofeev, Alexander Yu Misharin

Affiliation

¹ V.N. Orekhovich Institute of Biomedical Chemistry RAMS, Moscow, Russia.

PMID: 20702093
DOI: 10.1016/j.bmcl.2010.07.075

Abstract

Reaction of 17alpha-bromo-21-iodo-3beta-acetoxypregn-5-en-20-one with ammonia, primary, and secondary amines is simple and convenient method for preparation of [17(20)E]- and [17(20)Z]-pregna-5,17(20)-dien-21-oylamides. Synthesis and characteristics of 12 related amides are presented. Primary testing on cells proliferation indicated differing effects of synthesized compounds on androgen insensitive MCF-7 cells and androgen sensitive LNCaP cells.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Androgens / metabolism
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology*
Breast Neoplasms / drug therapy
Carcinoma / drug therapy
Cell Line, Tumor
Cell Proliferation / drug effects*
Female
Humans
Male
Pregnenolone / analogs & derivatives*
Pregnenolone / chemical synthesis
Pregnenolone / pharmacology*
Prostatic Neoplasms / drug therapy

Substances

Androgens
Antineoplastic Agents
Pregnenolone