Acta Pharm. 58 (2008) 29-42

full paper

Original research paper


Synthesis of progesterone heterocyclic derivatives of potential antimicrobial activity



1Department of Organic Chemistry, Faculty of Pharmacy, University of Modern Sciences and Arts (MSA), October City, Giza, Egypt

2Hormone Department, National Research Centre, Dokki, Giza, Egypt

Accepted February 5, 2008


The aim of this work was to synthesize steroidal heterocycles and to elucidate the potential role of these compounds as antimicrobial agents. The synthesis of steroidal heterocycles containing the pyrazole, isoxazole, thiazole, pyrane, pyridine, pyridazine, or benzopyrane ring attached to the pregnene nucleus is reported. Progesterone (1) reacts with dimethyl formamide dimethyl acetal to form enamine 2. Heterocyclization of 2 with hydrazines, hydroxylamine, glycine, ethylacetoacetate or cyanomethylene afforded novel steroidal heterocyclic derivatives. The in vitro antimicrobial evaluation showed that all synthesized compounds show activity against the used strains of Gram positive bacteria and fungi.


Keywords: progesterone, enamine, pyrazole, pyrane, antimicrobial