Pyridone-carboxylic Acids as Antibacterial Agents. I. Synthesis and Antibacterial Activity of 1-Alkyl-1,4-dihydro-4-oxo-1,8-and 1,6-naphthyridine-3-carboxylic Acids

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概要

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• Condensation of 2-amino-6-chloropyridine (1) with diethyl ethoxymethylenemalonate gave the aminomethylenemalonate 2,which upon thermal cyclization (Gould-Jacobs reaction) afforded ethyl 7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (3). Alkylation of 3 produced the 1-alkyl derivative 4. Substitution of 4 with a cyclic amine gave ethyl 7-substituted 1-alkyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (5). The ester 5 was hydrolyzed to the corresponding carboxylic acid 6. 7-Substituted 1-alkyl-1,4-dihydro-4-oxo-1,6-naphthyridine-3-carboxylic acids (20) were also synthesized from 4-amino-2-chloropyridine (13) in a similar manner. The in vitro antibacterial activity was enhanced by the presence of a cyclic amine at position 7 on 6 and 20. In general, the 1,8-naphthyridine 6 was more active than the 1,6-naphthyrdine counterpart 20. 1-Ethyl-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid (6e) (an analog of both pipemidic acid and nalidixic acid) was comparable to pipemidic acid but superior to nalidixic acid in terms of activity in vitro against Pseudomonas aeruginosa.

• 公益社団法人日本薬学会の論文
• 1982-07-25

著者

• 廣瀬 徹

  大日本製薬株式会社 総合研究所

• 広瀬 徹

  Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• 松本 純一

  Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.

• 松本 純一

  Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• 廣瀬 徹

  Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• 三塩 晋作

  大日本製薬株式会社 総合研究所

• 三塩 晋作

  Research Laboratories, Dainippon Pharmaceutical Co., Ltd.

• 南 新作

  Research Laboratories, Dainippon Pharmaceutical Co., Ltd.

• 南 新作

  大日本製薬株式会社 総合研究所(現):帝国化学産業株式会社研究所

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