Synthesis of progesterone heterocyclic derivatives of potential antimicrobial activity.
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, ethyl acetoacetate 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.
Mohareb
Rafat M
RM
Department of Organic Chemistry, Faculty of Pharmacy, University of Modern Sciences and Arts (MSA), October City, Giza, Egypt. raafat-mohareb@yahoo.com
Hana
Hanaa Y
HY
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D006090:Gram-Negative Bacteria / Q000187:drug effects / Q000254:growth & development; D006094:Gram-Positive Bacteria / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011374:Progesterone / Q000031:analogs & derivatives*; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D013260:Steroids, Heterocyclic; D011374:Progesterone