

HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
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51st Congress of Heterocyclic Chemistry will be held from September 15, 2022 to September 17, 2022. For more information see: http://www.chem.eng.osaka-u.ac.jp/~minakata-lab/hetero51/
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to 2 September 2022. The Congress website can be found here: https://ishc.chem.uci.edu/, and links to registration and housing are open.
June 6, 2022
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December 24, 2019
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e-Journal
Abstract
Published online: 20th July, 2018
■ Structure–Activity Relationship Study of Gatastatin Based on the Topliss Tree Approach
Ichiro Hayakawa,* Shuya Shioda, Takumi Chinen, Takeo Usui, and Hideo Kigoshi*
*Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan
Abstract
Various analogues of gatastatin, a γ-tubulin-specific inhibitor, were designed and synthesized by systematically optimizing the aromatic ring at the O7-benzyl group in accordance with an operational Topliss tree, and their biological activities were evaluated. Some derivatives showed stronger cytotoxicity against HeLa cells than gatastatin. Especially, the cytotoxicity of the meta-chloro derivative was about 18-fold stronger than that of gatastatin. However, these derivatives did not exhibit binding ability to the yeast γ-tubulin small complex or inhibitory activity against α,β-tubulin polymerization. These results suggested that γ-tubulin strongly recognized the unsubstituted phenyl ring of the O7-benzyl group in gatastatin.
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