Inhibitive effects of structurally modified azasteroids and related nitrogen containing steroids on insect growth and development.
A number of azasteroids and other nitrogen containing steroids with a modified nucleus or side chain were prepared and tested for their inhibitory effects on the growth and development of several species of insects. Structure-activity studies showed that compounds with a structurally related steroid nucleus and side chain were approximately equal in inhibitory activity for a particular species. The replacement of the tertiary amino group in the side chain of the 5beta-steroid with other nitrogen substituents, such as nitro, cyano, acetylamino, or a quaternary ammonium salt, resulted in a considerable loss of inhibitive activity in the tobacco hornworm or the yellowfever mosquito. However, certain modifications of the azasteroid nucleus resulted in compounds that still retained high biological activity. As a result, a compound was synthesized that lacked the A and B rings of the steroid nucleus and that inhibited insect growth, molting, and metamorphosis and the delta24-sterol reductase enzyme system of the tobacco hornworm.
D000330:Aedes; D000818:Animals; D001378:Azasteroids / Q000138:chemical synthesis; D002757:Cholanes; D002770:Cholenes; D006793:Houseflies; D007313:Insecta / Q000201:enzymology / Q000254:growth & development; D007814:Larva; D007915:Lepidoptera; D008675:Metamorphosis, Biological / Q000187:drug effects; D010088:Oxidoreductases / Q000037:antagonists & inhibitors; D013256:Steroids / Q000138:chemical synthesis; D013260:Steroids, Heterocyclic; D013329:Structure-Activity Relationship; D014231:Tribolium
D001378:Azasteroids; D002757:Cholanes; D002770:Cholenes; D013256:Steroids; D013260:Steroids, Heterocyclic; D010088:Oxidoreductases