Three-dimensional common-feature hypotheses for octopamine agonist1-arylimidazolidine-2-thiones

Akinori Hirashima, Masako Morimoto, Hiroto Ohta, Eiichi Kuwano, Eiji Taniguchi, Morifusa Eto

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10 Citations (Scopus)

Abstract

Three-dimensional pharmacophore hypotheses were built from a set of 10 octopamine (OA) agonist 1-arylimidazole-2(3H)-thiones (AIHTs) and 1-arylimidazolidine-2-thiones (AITs). Among the ten common-featured models generated by program Catalyst/HipHop, a hypothesis including a hydrophobic aromatic (HpAr), three hydrophobic aliphatic (HpAl) and a hydrogen-bond acceptor lipid (HBAl) features was considered to be (important in evaluating the OA-agonist activity. Active OA agonist 2,6-Et)2 AIT mapped well onto all the HpAr, HpAl and HBAl features of the hypothesis. On the other hand, inactive compound (2,6-Et)2 AIHT was shown to be difficult to achieve the energetically favorable conformation which is found in the active molecules in order to fit the 3D common-feature pharmacophore models. The present studies on OA agonists demonstrate that an HpAr, three HpAls and an HBAl sites located on the molecule seem to be essential for OA-agonist activity.

Original languageEnglish
Pages (from-to)56-68
Number of pages13
JournalInternational journal of molecular sciences
Volume3
Issue number2
DOIs
Publication statusPublished - Feb 2002

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Molecular Biology
  • Spectroscopy
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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