Steroid derivatives of cysteamine and cysteine

Abstract

A number of androstenone, estrone, and pregnenone derivatives of cysteamine have been prepared by reacting the steroid amines with ethylene monothiolcarbonate. The amides of androstenone carboxylic acid with mercaptoethylamine and cysteine have also been prepared.

Synthesis of Estradiol-Cinnamide Conjugates

“…22 3-O-Methyl-17β-aminoestra-1,3,5(10)-triene-3-ol (5b) and 17βaminoestra-1,3,5(10)-triene-3-ol (5a) were prepared from the corresponding steroidal oximes 23 by reduction with sodium in refluxing propanol. 24 The synthesis of steroids 1b-1e has been described earlier. 12 3 3-O-Methyl-17β-aminoestra-1,3,5 (10),6-tetraene-3-ol (5c): Aluminium powder (297 mg, 11 mmol) was added to a solution of estrone oxime 4c (320 mg, 1.07 mmol) in EtOH (10 mL).…”

Simple amidation of unprotected phenol-containing 2-alkenoic acids

“…19,20,21 All the amines were liquids, except the 4-hydroxy-3-methoxybenzylamine hydrochloride (11d), the 3-O-methyl-17β-aminoestra-1,3,5(10)-trien-3-ol (11g) and the 17β-aminoestra-1,3,5(10)-trien-3-ol (11h). Dioxan was dried and distilled from Na under inert atmosphere.…”

“…3-O-Methyl-17βaminoestra-1,3,5( 10)-trien-3-ol (11g) was prepared from the corresponding 17-oxime by reduction with Na in refluxing n-propanol analogous to a known procedure, the non-protected 17β-aminoestra-1,3,5( 10)-trien-3-ol (11h) was prepared by the same procedure or by reduction with LiAlH 4 . 19,20,21 All the amines were liquids, except the 4-hydroxy-3-methoxybenzylamine hydrochloride (11d), the 3-O-methyl-17β-aminoestra-1,3,5( 10)-trien-3-ol (11g) and the 17β-aminoestra-1,3,5( 10)-trien-3-ol (11h). The reaction with these last amines was performed using an aliquot of dioxan and with microwave cycles of 1 minute each.…”