Synthesis, antibacterial and antifungal activities of 6,5 fused steroidal oxazoles in cholestane series.
Herein, we report a convenient one-pot synthesis of 2'-amino-5alpha-cholest-6-eno [6,5-d] oxazole derivatives (4-6). The synthesis involves the reaction of cholestan-6-ones (1-3) with urea and iodine. The structural assignment of the products was confirmed on the basis of IR, (1)H NMR, (13)C NMR, and Mass spectra which find support from comparison with authentic samples. The antibacterial activity of all the synthesized compounds was tested in vitro by the disk diffusion assay against three Gram-positive and three Gram-negative strains of bacteria. All the synthesized compounds were also tested for their inhibitory action against five strains of fungus and then the minimum inhibitory concentration (MIC) of all the synthesized compounds were determined. Compounds (4-6) showed inhibitory action against both types of the bacteria (Gram-positive and Gram-negative) and five strains of fungi are good antimicrobial agents. Chloramphenicol (30 microg) was used as standard drug in case of bacteria and nystatin was used as a standard drug in case of fungi.
Shamsuzzaman
Department of Chemistry, Aligarh Muslim University, Aligarh 202 002, India. shams_chem@rediffmail.com
Khan
Mohd Shaheen
MS
Alam
Mahboob
M
Tabassum
Zishan
Z
Ahmad
Anis
A
Khan
Asad U
AU
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002776:Cholestanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D007455:Iodine / Q000737:chemistry; D013058:Mass Spectrometry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014508:Urea / Q000737:chemistry
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D002776:Cholestanes; D010080:Oxazoles; D013256:Steroids; D014508:Urea; D007455:Iodine