Quantitative structure-activity studies of insect growth regulators xiv. Three-dimensional quantitative structure-activity relationship of ecdysone agonists including dibenzoylhydrazine analogs

✍ Scribed by Nakagawa, Yoshiaki; Hattori, Kazunari; Shimizu, Bun-ichi; Akamatsu, Miki; Miyagawa, Hisashi; Ueno, Tamio

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 326 KB
• Volume: 53
• Category: Article
• ISSN: 1526-498X
• DOI: 10.1002/(sici)1096-9063(199808)53:4<267::aid-ps765>3.0.co;2-u

✦ Synopsis

N-tert-Butyl-N,N@-dibenzoylhydrazines such as tebufenozide (RH-5992) mimic the action of a molting hormone, 20-hydroxyecdysone, and cause premature molting of larvae leading to their death. Previously, it was shown that one of the benzoyl moieties in dibenzoylhydrazines plays a role similar to that of the aliphatic side chain at the C-17 position of ecdysones. In the present study, N-benzoyl-N@-benzylhydrazine, N,N@-dibenzylhydrazine, and N-alkanoyl-N@-benzoylhydrazine analogs have been synthesized to compare the e †ects of two carbonyl groups as well as two benzene rings of dibenzoylhydrazine. The quantitative structureÈactivity relationship of ecdysone agonists including dibenzoylhydrazine analogs was analyzed three-dimensionally using the CoMFA (comparative molecular Ðeld analysis) procedure. The CoMFA results suggested that the two carbonyl oxygen atoms of the diacylhydrazine skeleton probably correspond to the oxygens of the 20-and 22-OH groups of ecdysones, and that the benzoyl moiety located closer to the tert-butyl group is important for retaining high activity.

1998 SCI (