Analogues of androgen hormones with inverted configuration at carbons 5, 9, and 10.
On catalytic hydrogenation of Delta(9)-steroids (e.g. 3beta-hydroxy-5-methyl-19-nor-5beta-androst-9-en-17-one), four isomers were formed: 9alpha,10alpha-, 9alpha,10beta-, 9beta,10alpha- and 9beta,10beta-adducts. The product distribution was affected by the nature of the C-3 substituent. A chair conformation of A, B, and C rings was found in all of the products with the exception of the 9alpha,10alpha-adduct whose B ring adopts a twist boat conformation. The products were utilized for the synthesis of dihydrotestosterone analogues.
Kasal
Alexander
A
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming Square 2, CZ166 10 6 Dejvice, Prague, Czech Republic. kasal@uochb.cas.cz
Budesínský
Milos
M
Drasar
Pavel
P
D000728:Androgens / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D018736:DNA Adducts; D013196:Dihydrotestosterone / Q000138:chemical synthesis / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011487:Protein Conformation; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry*
D000728:Androgens; D018736:DNA Adducts; D013256:Steroids; D013196:Dihydrotestosterone; D002244:Carbon; D006859:Hydrogen