The Structure-Activity Relationships of Antibacterial L-5-Alkylthiomethylhydantoin <i>S</i>-Oxides and Related Compounds

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  • MIURA Yuzo
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University Present address: Research Laboratories, Nihon Nohyaku Co., Ltd.
  • TAHARA Satoshi
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University
  • MIZUTANI Junya

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Other Title
  • 抗菌性L-5-AlKkylthiomethylhydantoin <i>S</i>-oxides および関連化合物の構造と活性の関係
  • Hydantoin Derivatives of <i>S</i>-Alkyl-and Alkenyl-L-cysteine-<i>S</i>-oxides (Part II)

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Abstract

The structure-activity relationships of antibacterial L-5-alkylthiomethylhydantoin S-oxides and related compounds prepared were examined. S-Propyl-L-cysteine-S-oxide, its N-carbamoyl derivative and dl-3-alkylthio-2-methylpropionamide S-oxides which do not have hydantoin ring exhibited far less activities. 5-Alkyl- and alkenylthiomethyl-5-methylhydantoin S-oxides and 5-alkylthioethylhydantoin S-oxides bearing hydantoin structure did not have either any appreciable activity. From these results, it has strongly been suggested that the structure required for antibacterial activity is summarized as follows: (1) Hydantoin ring and (2) sulfoxide function should be necessary, (3) the hydrogen atom on the 5-C of the hydantoin ring is essential, and (4) the methylene-unit between the sulfur atom and the hydantoin ring is not two (or more), but one.

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