Acta Pharm. 58 (2008) 29-42
Original research paper
Synthesis of progesterone heterocyclic derivatives of potential
antimicrobial activity
RAFAT M. MOHAREB and HANAA Y. HANA
raafat_mohareb@yahoo.com
1Department of Organic Chemistry, Faculty of Pharmacy,
University of Modern Sciences and Arts (MSA), October City, Giza, Egypt
2Hormone Department, National Research Centre,
Dokki,
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