Novel pyrazolo, isoxazolo, and thiazolo steroidal systems and model analogs containing dimethyoxylaryl (or dihydroxylaryl) groups and derivatives. Synthesis, spectral properties, and biological activity.
The total syntheses of a series of vicinal-substituted dimethoxy and dihydroxy heterosteroids of the equilenin type and model analogs are described. A novel class of pyrazolo steroidal N-glucosides has also been synthesized. Compounds prepared were screened in vitro for growth inhibition of different microorganisms. Of these, 1-alpha-d-glucopyranosyl-4,5-dihydro-7-methyoxy-1H-benz[g]indazole tetraacetate (3) was quite active. For example, N-glucoside 13 inhibited the growth of Bacillus subtilis, Pseudomonas fluorescens, Staphylococcus aureus, and KB cells at moderate concentrations.
D001412:Bacillus subtilis / Q000187:drug effects / Q000254:growth & development; D002478:Cells, Cultured; D003864:Depression, Chemical; D006801:Humans; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000138:chemical synthesis*; D011551:Pseudomonas fluorescens / Q000187:drug effects / Q000254:growth & development; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D007555:Isoxazoles; D010080:Oxazoles; D011720:Pyrazoles; D013260:Steroids, Heterocyclic; D013844:Thiazoles