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

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)419-424
Number of pages6
JournalJournal of Pesticide Science
Volume21
Issue number4
DOIs
Publication statusPublished - Jan 1 1996

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Periplaneta
halogens
Halogens
Periplaneta americana
agonists
Thoracic Nerves
thiourea
Thiourea
enzyme activation
adenylate cyclase
Enzyme Activation
synthesis
chest
Adenylyl Cyclases
oxides
nerve tissue
chemical derivatives
energy
oxazolidine
mercuric oxide

All Science Journal Classification (ASJC) codes

  • Insect Science
  • Health, Toxicology and Mutagenesis

Cite this

Synthesis and Octopaminergic-Agonist Activity of 2-(Arylimino)oxazolidines and 2-(Substituted Benzylamino)-2-oxazolines. / Hirashima, Akinori; Pan, Canping; Katafuchi, Yumiko; Taniguchi, Eiji; Eto, Morifusa.

In: Journal of Pesticide Science, Vol. 21, No. 4, 01.01.1996, p. 419-424.

Research output: Contribution to journalArticle

Hirashima, Akinori ; Pan, Canping ; Katafuchi, Yumiko ; Taniguchi, Eiji ; Eto, Morifusa. / Synthesis and Octopaminergic-Agonist Activity of 2-(Arylimino)oxazolidines and 2-(Substituted Benzylamino)-2-oxazolines. In: Journal of Pesticide Science. 1996 ; Vol. 21, No. 4. pp. 419-424.
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