Novel pyrazolo, isoxazolo, and thiazolo steroidal systems and model analogs containing dimethoxylaryl (or dihydroxylaryl) groups and derivatives. Synthesis, spectral properties, and biological activity

Abstract

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.