

HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
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e-Journal
Abstract
Published online: 15th May, 2018
■ Preparation of Novel Bivalent Linker Mode Phenylboronic Acid Derivatives and Their Biological Evaluation
Makoto Furutachi, Ayaka Matsumoto, Tetsuya Tamenaga, Aya Sugita, Misato Kuroiwa, Kazumi Yokomizo, Jian-Rong Zhou, Nobuhiro Kashige, Fumio Miake, and Kunihiro Sumoto*
*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan
Abstract
We report a new route to the preparation of C2-symmetrical bivalent phenylboronic acids having alkyl linker groups in the molecule and results of biological evaluation of their biological activity and cytotoxic activity against Vero cells. Among the tested compounds, C2-symmetrical bivalent meta-oriented phenylboronic acid 2f (n=7) showed high cytotoxic activity (CC50=5.43 μM) against Vero cells. The results of an SAR study suggested that the presence of a C7-methylene linker group in the molecule is an important structural factor for expression of potential cytotoxic activities. A sugar recognition property of this C2-symmetrical geometric molecule was suggested by NMR analysis of compound 2f with methyl α-D-glucopyranoside 6.
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