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Short Paper | Regular issue | Vol 94, No. 9, 2017, pp.1748-1758
Published online, 14th July, 2017
DOI: 10.3987/COM-17-13745
■ Novel C2-Symmetrical Phenylboronic Acid Pinacol Esters with a Few Types of Linkers and Their Biological Activities

Makoto Furutachi, Toshiaki Gondo, Saho Goto, Saho Fuchigami, Kenta Ako, Yuki Oowada, Kazumi Yokomizo, Jian-Rong Zhou, Tomohiro Ishizaki, Takahiro Koga, 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 the preparation of new C2-symmetrical cyclic phenylboronic acid derivatives and their biological activities. New targeted C2-symmetrical molecules (1) were obtained in good to excellent yields by a primitive amide bond formation reaction using the reported method starting with amino-substituted phenylboronic acid pinacol esters 2. A few C2-symmetrical phenylboronic acid ester analogues such as 5 and 7 that have two urea groups in the linker junction were also prepared in order to evaluate antibacterial and antiviral activities. The results of a structure-activity relationship study are also described.