477904-23-7

Upstream product

• 24967-14-4 (3aS,9aS,9bS)-3a-Methyl-1,2,4,6,8,9,9a,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione 
• 62-53-3 aniline 

Downstream Products

• 477904-26-0 (3S,3aS,5aS,7R,9aS,9bS)-3-(Benzoyl-phenyl-amino)-7-ethoxy-3a-methyl-dodecahydro-6-aza-cyclopenta[a]naphthalene-6-carboxylic acid tert-butyl ester 
• 477904-25-9 (3S,3aS,5aS,9aS,9bS)-3-(Benzoyl-phenyl-amino)-3a-methyl-7-oxo-dodecahydro-6-aza-cyclopenta[a]naphthalene-6-carboxylic acid tert-butyl ester 
• 477904-27-1 (3S,3aS,5aS,7R,9aS,9bS)-7-Ethoxy-3a-methyl-3-phenylamino-dodecahydro-6-aza-cyclopenta[a]naphthalene-6-carboxylic acid tert-butyl ester 
• 477904-31-7 (+)-17β-(N-phenylamino)-(5β)-10-azaestr-1-en-3-one 
• 477904-19-1 (-)-17β-(N-phenylamino)-(5α)-10-azaestr-1-en-3-one 
• 477904-24-8 (3S,3aS,5aS,9aS,9bS)-3a-Methyl-7-oxo-3-phenylamino-dodecahydro-6-aza-cyclopenta[a]naphthalene-6-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of 17beta-N-substituted 19-Nor-10-azasteroids as inhibitors of human 5alpha-reductases I and II.

The synthesis of 17beta-[N-(phenyl)methyl/phenyl-amido] substituted 10-azasteroids has been accomplished by either the TiCl4- or TMSOTf-catalysed reaction of carbamates 11 and 12 with Danishefsky's diene. The reaction provided 5alpha-H isomers 3a-5a and 5beta-H isomers 3b-5b depending on the reaction conditions. Both epimers of each compound were tested against human 5alpha-reductase types I and II. Unexpectedly, 5beta-H compounds were found more active than their 5alpha-H counterparts, the best inhibitors being 3b (IC50=279 and 2000 nM toward isoenzyme I and II, respectively) and 5b (IC50=913 and 247 nM toward isoenzymes I and II, respectively).