An approach towards the development of progesterone antagonists: synthesis of 7 alpha/7 beta-aryl androstene derivatives.
Synthesis of 3 beta,17 beta-dihydroxy-7 alpha/7 beta-(4-hydroxyphenyl)-androst-5-ene 3,17-diacetate (4 and 5, R = H) and 3 beta,17 beta-dihydroxy-7 alpha/7 beta-(4-methoxyphenyl)-androst-5-ene 3,17-diacetate (4 and 5, R = Me) have been carried out by Friedel-Crafts reaction on 3 beta,7,17 beta-trihydroxy-androst-5-ene 3,17-diacetate (3, R = H) with phenol and anisole, respectively. Compounds 4 (R = H) and 5 (R = H) have been separated and their stereochemistry assigned on the basis of COSY and NOE experiments.
Negi
A S
AS
Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India.
Dwivedy
I
I
Roy
R
R
Ray
S
S
D000737:Androstenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000840:Anisoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011374:Progesterone / Q000037:antagonists & inhibitors*; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C095627:3,17-dihydroxy-7-(4-hydroxyphenyl)-androst-5-ene 3,17-diacetate; D000737:Androstenols; D000840:Anisoles; D010636:Phenols; C095628:3,17-dihydroxy-7-(4-methoxyphenyl)-androst-5-ene 3,17-diacetate; D011374:Progesterone