- Synthesis and Biological Activity of 2-Aminothiazolines and 2-Mercaptothiazolines as Octopaminergic Agonists
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2-Aminothiazoline derivatives were synthesized by both hydrochloric acid-catalyzed cyclization of thiourea and 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 33percent 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 of octopamine.The β-adrenergic antagonist propanolol was less potent.These data suggest that III-16 is a potent and selctive agonist of octopamine-activated adenylate cyclase.Aminothiazolines which activated adenylate cyclase by 10-87percent 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.
- Hirashima, Akinori,Yoshii, Yutuka,Eto, Morifusa
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p. 2537 - 2546
(2007/10/02)
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- On the Reaction of 2-Chloroethylisothiocyanate with Aromatic Amines
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The reaction of aromatic amines with 2-chloroethylisothiocyanate 2 to give 2-arylaminothiazolines 1 was investigated.The course of this reaction was found to depend on the electronic nature of the amine and the reaction conditions.With arylamines that are
- Outcalt, Russell J.
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p. 1425 - 1428
(2007/10/02)
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