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Short Paper | Regular issue | Vol 89, No. 12, 2014, pp.2745-2759
Published online, 14th November, 2014
DOI: 10.3987/COM-14-13106
Reaction of 5-Methylenehydantoins and Their Chemical Modification to Twin-Drug Type Symmeteical Molecules

Fumiko Fujisaki, Ryou Fujiwara, Miriko Okabe, Ayumi Naito, Enko Fukami, Hatsumi Aki, 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 chemical modifications of 5-methylenehydantoins (3a-e) with various amine nucleophiles to 5-substituted hydantoins and transformations of the obtained hydantoins to new symmetrical twin-drug type bivalent molecules 12 and 13. We also report 5-methylenehydantoin derivatives (3a) with some symmetrical diamines such as piperadine, ethylene-1,2-diamine, and 1,2-phenylenediamine. From trials using diamines such as ethylene-1,2-diamine and 1,2-phenylenediamine, hydantoin ring-opened products 10 and 11 were isolated predominantly.