Synthesis of New 5-Substituted Hydantoins and Symmetrical Twin-Drug Type Hydantoin Derivatives

Fumiko Fujisaki; Hatsumi Aki; Ayumi Naito; Enko Fukami; Nobuhiro Kashige; Fumio Miake; Kunihiro Sumoto

doi:10.1248/cpb.c14-00017

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Synthesis of New 5-Substituted Hydantoins and Symmetrical Twin-Drug Type Hydantoin Derivatives

Fumiko Fujisaki, Hatsumi Aki, Ayumi Naito, Enko Fukami, Nobuhiro Kashige, Fumio Miake, Kunihiro Sumoto

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Keywords: hydantoin, regioselective, antibacterial activity, isothermal titration calorimetry, bivalent twin-drug, sulfated glycosaminoglycan

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2014 Volume 62 Issue 5 Pages 429-438

DOI https://doi.org/10.1248/cpb.c14-00017

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Abstract

In connection with our studies on hydantoin derivatives, a conventional regioselective chemical transformation of 5-methylene hydantoins 4a–c to 5-aminomethyl-substituted hydantoins 5–10 or to 5-amino-5-methyl-disubstituted hydantoins 11–14 is described. Synthesis of bivalent twin-drug type hydantoin derivatives 19–24 and the binding property of a bivalent symmetrical hydantoin derivative 24b to sulfated glycosaminoglycans are also described.

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