title: Synthesis and antimicrobial evaluation of some novel cholestane heterocyclic derivatives.
abstract: This study was performed to investigate the reactivity of 5alpha-cholestan-3-one (1) towards various chemical reagents to produce new steroidal heterocyclic derivatives. The aminothieno[2, 3:2, 3]cholestane derivative 2 was synthesized according to Gewald's conditions. The diazonium salt of compound 2 coupled with malononitrile to afford dicyanomethylenhydrazinothieno[2', 3':2, 3]cholestane derivative 5. The behavior of compound 5 towards nitrogen nucleophiles and several active methylene reagents was investigated. Additionally, a variety of steroidal heterocyclic derivatives like compounds 15a, b-22a, b were synthesized starting with 5alpha-cholestan-3-one (1). The structures of the compounds were established based on the analytical and spectral data. The in vitro antimicrobial activity of some newly synthesized compounds against bacteria and fungi was studied.
authors.affiliation: Hormone Department, National Research Centre, Dokki, Giza, Egypt. gamalae@hotmail.com
authors.forename: Gamal A
authors.initials: GA
authors.lastname: Elmegeed
authors.forename: Wagnat W
authors.initials: WW
authors.lastname: Wardakhan
authors.forename: Magdi
authors.initials: M
authors.lastname: Younis
authors.forename: Nadia A
authors.initials: NA
authors.lastname: Louca
mesh_terms: D000667:Ampicillin / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002776:Cholestanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D066298:In Vitro Techniques; D008826:Microbial Sensitivity Tests / Q000379:methods; D009761:Nystatin / Q000494:pharmacology
chemical_list: D000890:Anti-Infective Agents; D002776:Cholestanes; D006571:Heterocyclic Compounds; D009761:Nystatin; D000667:Ampicillin