Total synthesis of 1,11- and 3,11-diazasteroids.
The 2- and 6-methoxy derivatives of 8-aminoquinoline, as well as 5-aminoisoquinoline, condensed with 2-ethoxycarbonylcyclopentanone to give tricyclic intermediates in 86-90% yield. These secosteroids were cyclized in 35-69% yield with polyphosphoric acid to 2-methoxy-1,11-diaza-, 7-methoxy-1,11-diaza-, and 3,11-diaza-1,3,5,7,9,13-gonahexaen-12-ones, respectively. The latter exhibits slight antileukemic activity.
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000627:therapeutic use; D001378:Azasteroids / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D007942:Leukemia, Experimental / Q000188:drug therapy; D051379:Mice; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis*
D000970:Antineoplastic Agents; D001378:Azasteroids; D013260:Steroids, Heterocyclic