Quantitative structure-activity studies of octopaminergic 2-(arylimino)thiazolidines and oxazolidines against the nervous system of Periplaneta americana L.

Akinori Hirashima, Jun Tomita, Canping Pan, Eiji Taniguchi, Morifusa Eto

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Abstract

The quantitative structure-activity relationship (QSAR) of octopaminergic 2-(arylimino)thiazolidines (AITs) and 2-(arylimino)oxazolidines (AIOs) against the thoracic nerve cord of the American cockroach, Periplaneta americana L., was analysed using reported physicochemical parameters and regression analysis. The more electron-donating, the less bulky at m-position, and the more hydrophobic the substituent, the greater the activity. The plots of observed log V(max) values against calculated log V(max) values having substituents on the m-position deviated downwards from those of compounds having substituents at the o- and/or p-positions. The more hydrophobic and the more electron-withdrawing the substituent, the greater the activity. AIO with a 2,3,4-trichlorophenyl group (58) was more active than its thiazolidine derivative, 2-(2,3,4-trichlorophenylimino)thiazolidine (38) in terms of V(max):V(max) of 58 was 30% relative to octopamine (OA), whereas that of 38 has been 9% relative to OA, respectively. Superimposition of energy-minimized OA and 58 revealed structural and conformational similarities that might account for the high activity of 58.

Original languageEnglish
Pages (from-to)2121-2128
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume5
Issue number12
DOIs
Publication statusPublished - Dec 1 1997

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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