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• Hirashima, A
• Morimoto, M
• Ohta, H
• Kuwano, E
• Taniguchi, E
• Eto, M
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• Hirashima, A
• Morimoto, M
• Ohta, H
• Kuwano, E
• Taniguchi, E
• Eto, M
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• Hirashima, A
• Morimoto, M
• Ohta, H
• Kuwano, E
• Taniguchi, E
• Eto, M

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Int. J. Mol. Sci. 2002, 3(2), 56-68; doi:10.3390/i3020056

Article

Three-Dimensional Common-Feature Hypotheses for Octopamine Agonist 1-Arylimidazolidine-2-Thiones

Akinori Hirashima ^1,* , Masako Morimoto ² , Hiroto Ohta ² , Eiichi Kuwano ¹ , Eiji Taniguchi ³  and Morifusa Eto ⁴

¹ Department of Applied Genetics and Pest Management, Faculty of Agriculture, Graduate School, Kyushu University, 6-10-1 Hakozaki, Fukuoka 812-8581, Japan ² Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, 6-10-1 Hakozaki, Fukuoka 812-8581, Japan ³ School of Agriculture, Kyushu Tokai University, Kumamoto 869-1404, Japan ⁴ Kyushu Women’s University, 1-1 Jiyugaoka, Yahatanishi-ku, Kita-Kyushu, Fukuoka 807-8586, Japan

* Author to whom correspondence should be addressed.

Received: 4 October 2001 / Accepted: 22 January 2002 / Published: 28 February 2002

Download PDF Full-Text [129 KB, uploaded 28 August 2008 16:06 CEST]

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-Et₂ AIT mapped well onto all the HpAr, HpAl and HBAl features of the hypothesis. On the other hand, inactive compound 2,6-Et₂ 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.

Keywords: Octopamine agonist; Common-feature hypothesis; Periplaneta americana; Pharmacophore; HipHop

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