Synthesis and antimicrobial studies of chalconyl pregnenolones

An efficient and facile synthesis of 17-chalconyl derivatives of pregnenolone and their evaluation as antimicrobial agents against various microbial strains is reported. The scheme involves the transformation of the starting pregnenolone acetate into pregnenolone, conversion of pregnenolone to the corresponding chalcone derivatives. The compounds 3a–3j showed significant antimicrobial activity against all microbial strains used for testing.

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► D-ring substituted chalconyl pregnenolones synthesized.
► Almost all compounds possess promising antimicrobial activity.
► The results are of importance as this opens a new field of research.
► The study will initiate new insights into the development of steroidal antimicrobials.