Synthesis and biological activity of some further cyclopenta[a]phenanthrenes.
16,17-Dihydro-11-methoxy-15H-cyclopenta[a]phenanthrene was synthesized by two different routes and tested for carcinogenicity in Tylers Original (TO) and SENCAR strain of mice by repeated application and initiation/promotion regime. 16,17-Dihydro-11-hydroxy-15H-cyclopenta[alpha]phenanthrene was also tested for carcinogenicity in the TO strain by repeated application. Surprisingly with both of these compounds, which lack conjugation in ring D, one of the ingredients essential for biological activity appears to be carcinogenic. It is tempting to speculate whether these compounds undergo metabolic oxidation in the skin at the benzylic C-17 position.
Bhatt
T S
TS
Joint Academic Unit of Obstetrics, Gynaecology and Reproductive Physiology, London Hospital Medical College, UK.
D000736:Androstenes / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002273:Carcinogens; D002277:Carcinoma / Q000139:chemically induced*; D051379:Mice; D010212:Papilloma / Q000139:chemically induced*; D012878:Skin Neoplasms / Q000139:chemically induced*; D013329:Structure-Activity Relationship
D000736:Androstenes; D002273:Carcinogens; C057010:16,17-dihydro-11-methoxy-15H-cyclopenta(a)phenanthrene