Synthesis of 17-(2-Methoxy-3-oxazolin-4-yl)-, 17-(3-Oxazolin-4-yl)-, and 17-(2-Oxazolin-4-ylidene) Substituted Steroids and Their Use as Precursors of Corticosteroids

Novel 17-Azolyl Steroids, Potent Inhibitors of Human Cytochrome 17α-Hydroxylase-C17,20-lyase (P45017α): Potential Agents for the Treatment of Prostate Cancer

“…Chemistry. Although a variety of C-17 azole androstane steroids are known − and the related Δ 16 -17 azole counterparts in which the azole is attached to the steroid nucleus through a carbon atom of the heterocycle have been prepared, ,, the isomeric compounds of this paper, in which the azole is attached to the steroid nucleus via a nitrogen of the azole, appear to constitute a new class of compounds. We have previously reported the synthesis of two of these compounds ( 6 and 17 ) .…”

Potent CYP17 inhibitors: improved syntheses, pharmacokinetics and anti-tumor activity in the LNCaP human prostate cancer model

“…Hitherto unreported 13 C NMR data of the VN/85-1 and VN/87-1, presented in Section 6, provide complete characterization of the two inhibitors. The 13 C NMR chemical shifts were assigned by comparison with reported values for closely related compound [20,21] and with the aid of their respective 1 H-13 C 2D NMR chemical shifts correlation spectra.…”

p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

“…Synthesis of oxazoles 30 from TosMIC and aldehydesEsters 33 also react with TosMIC in the presence of 2 equivalents of n-BuLi at À70 to 0 C to form 4-tosyloxazoles(34). The dianion of TosMIC is essential to act as a nucleophile during the course of its reaction with the ester carbonyl function [26] (Scheme 15).…”

“…The only exception is the reaction with pyrrole-2-carbaldehyde, leading to formation of 3-tosylpyrolo[1,2-c]pyrimidine[32]. TosMIC and monosubstituted TosMIC homologs (36) react with ,-unsaturated aldehydes (37) to form oxazoles 38[33] (Scheme 16).Similarly, the monosubstituted derivative of TosMIC (39) on reaction with formaldehyde forms oxazole 40[34] (Scheme 17). Substituted and 4,5-disubstituted oxazoles have recently been synthesized from the reaction of aryl-substituted TosMIC reagents with simple and multifunctional aldehydes[35].…”