Synthesis and in vitro biological evaluation of ring B abeo-sterols as novel inhibitors of Mycobacterium tuberculosis

摘要

A series of 3β-hydroxy steroid analogues possessing a contracted cyclopentane B-ring were prepared based on the initial activity screening of a recently reported naturally occurring marine 5(6 →7)abeo-sterol against Mycobacterium tuberculosis. All of the novel ring B abeo-sterols synthesized showed good inhibitory activity, whereas none of the starting steroids based on the common 3β-hydroxy-Δ⁵-cholestane nucleus, proved to be active. Therefore, the 5(6 →7)abeo-sterol nucleus present in compounds >3, >5, >7, >9, and >11 represents a novel scaffold for the development of new antitubercular agents.