Synthesis and biological activity of several steroidal oximes

Abstract

Steroidal oximes and their derivatives are known to exhibit anti-inflammatory, anticancer, and other types of physiological activity [1, 2]. In continuation of structure–activity relationship studies of 5 -steroids [3], we synthesized steroidal oximes 1–7 and studied their antimicrobial and anti-inflammatory activity. The starting material for synthesizing 1–7 was 5 -pregnenolone acetate, which was prepared by the method developed previously by us [4]. Oximes 1–6 were synthesized by the known method [5] from the corresponding ketones whereas 5 -pregnen-2one-20 (7) was obtained for the first time from ketone 8 using its tosylation (9), dehydrotosylation (10) [6, 7], and reaction of 10 with hydroxylamine hydrochloride in Py (Scheme 1).