Synthesis and Biological Activity of 2-Aminothiazolines and 2-Mercaptothiazolines as Octopaminergic Agonists

Akinori Hirashima, Yutaka Yoshii, Morifusa Eto

Research output: Contribution to journalArticle

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Abstract

2-Aminothiazoline derivatives were synthesized by both hydrochloric acid-catalyzed cyclization of thiourea and by cyclization of β-aminoalkyl hydrogen sulfate with isothiocyanate in the presence of sodium hydroxide. Substituted 2-mercaptothiazoline derivatives were prepared by alkylation or acylation of the sodium salt of 2-mercaptothiazoline, which was obtained from β-aminoalkyl hydrogen sulfate with carbon disulfide. 2-(4-Chloro-o-toluidino)-2-thiazoline (III-16) was 33% as effective as octopamine at 100 µM in stimulating adenylate cyclase of Periplaneta americana ventral-nerve-cord homogenates. Its activity was nonadditive to the activity of octopamine. Stimulation of nerve-cord adenylate-cyclase activity by III-16 was inhibited by several antagonists, including mianserin, cyproheptadine, chlorpromazine and gramine. The rank-order ability of these antagonists to block the activation by III-16 was identical to the rank-order ability of the same antagonists to block enzyme activation by octopamine. The β-adrenergic antagonist propranolol was less potent. These data suggest that III-16 is a potent and selective agonist of octopamine-activated adenylate cyclase. Aminothiazolines which activated adenylate cyclase by 10-87% relative to octopamine also had acaricidal activity at 300 ppm, indicating a correlation between the in vitro octopaminergic-agonist activity and in vivo acaricidal activity of aminothiazolines.

Original languageEnglish
Pages (from-to)2537-2545
Number of pages9
JournalAgricultural and Biological Chemistry
Volume55
Issue number10
DOIs
Publication statusPublished - Jan 1 1991

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Octopamine
octopamine
Bioactivity
adenylate cyclase
agonists
bioactive properties
Adenylyl Cyclases
synthesis
antagonists
Cyclization
Sulfates
hydrogen
Hydrogen
sulfates
gramine
chemical derivatives
adrenergic antagonists
Chemical activation
cyproheptadine
carbon disulfide

All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)
  • Agricultural and Biological Sciences(all)

Cite this

Synthesis and Biological Activity of 2-Aminothiazolines and 2-Mercaptothiazolines as Octopaminergic Agonists. / Hirashima, Akinori; Yoshii, Yutaka; Eto, Morifusa.

In: Agricultural and Biological Chemistry, Vol. 55, No. 10, 01.01.1991, p. 2537-2545.

Research output: Contribution to journalArticle

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