Synthesis and Octopaminergic-Agonist Activity of 2-(Arylimino)oxazolidines and 2-(Substituted Benzylamino)-2-oxazolines

Akinori Hirashima, Canping Pan, Yumiko Katafuchi, Eiji Taniguchi, Morifusa Eto

研究成果: Contribution to journalArticle査読

16 被引用数 (Scopus)

抄録

2-(Arylimino)oxazolidines (AIOs) and 2-(substituted benzylamino)-2-oxazolines (SBOs) were obtained by cyclodesulfurizing the corresponding thiourea with yellow mercuric oxide. The activity for stimulating adenylate cyclase prepared from thoracic nerve cords of the American cockroach Periplaneta americana L. was examined by these compounds. Greater enzyme activation appeared to result from alkyl substitution at the 2, 6-positions or 2-alkyl 4-halogen at the phenyl ring of AIOs. A halogen in the m- and/or p-position, or methyl group at p-position seems to be a favorable substituent on the phenyl ring of SBO compounds for octopaminergic-agonist activity. SBO with a 3, 4-dichlorophenyl group (36) was less active than its thiazoline derivative, 2-(3, 4-dichlorophenylamino)-2-thiazoline (CBT) in terms of Ka and Vmax: Ka and Vmax of 36 were 2.3 µm and 29% relative to OA, whereas those of CBT have been 0.40 µm and 53% relative to OA, respectively. Superimposition of energy-minimized OA and CBT revealed structural and conformational similarities that might account for the high activity of CBT.

本文言語英語
ページ(範囲)419-424
ページ数6
ジャーナルJournal of Pesticide Science
21
4
DOI
出版ステータス出版済み - 1996

All Science Journal Classification (ASJC) codes

  • 昆虫科学
  • 健康、毒物学および変異誘発

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