7-(2-Aminomethyl-1-azetidinyl)-4-oxoquinoline-3-carboxylic Acids as Potent Antibacterial Agents : Design, Synthesis, and Antibacterial Activity

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概要

• 論文の詳細を見る

• 2-Aminomethyl-1-azetidinyl, -1-pyrrolidinyl, and -1-piperidinyl groups were designed as novel C-7 substituents for potential antibacterial quinolone agents. Of the three substituents, the 2-aminomethyl-1-azetidinyl group (compound 12a) was found to be the most favorable for enhancing the activity of the 6,8-difluoroquinoline molecule 12. Therefore the 2-aminomethyl-1-azetidinyl group was introduced into a variety of quinolines (giving 24-26a, and 28a) and naphthyridines (giving 31a and 32a). Through optical resolution of 1-benzylazetidine-2-carboxamide (19) and chiral synthesis of its R-isomer, both enantiomers of 2-aminomethyl-1-azetidinyl quinolines 12a and 24-26a were also prepared. The most active of all the compounds was 5-amino-6,8-difluoroquinoline (R)-26a. The activity of (R)-26a was more potent than those of the corresponding 1-piperazinyl derivative (3) and sparfloxacin (1), and was comparable to those of the corresponding 3-amino-1-pyrrolidinyl (4), 3-aminomethyl-1-pyrrolidinyl (5), and 3-amino-1-azetidinyl (6) derivatives.

• 公益社団法人日本薬学会の論文
• 1998-05-15

著者

• Chiba K

  Discovery Research Laboratories Ii Dainippon Pharmaceutical Company Ltd.

• Tominaga Y

  Discovery Research Laboratories Ii Dainippon Pharmaceutical Company Ltd.

• FUJITA Masahiro

  Discovery Research Laboratories II, Dainippon Pharmaceutical Company, Ltd.,

• CHIBA Katsumi

  Discovery Research Laboratories II, Dainippon Pharmaceutical Company, Ltd.,

• TOMINAGA Yukio

  Discovery Research Laboratories II, Dainippon Pharmaceutical Company, Ltd.,

• Chiba K

  Laboratory Of Bio-organic Chemistry Tokyo University Of Agriculture And Technology

• Hino K

  Discovery Research Laboratories Ii Dainippon Pharmaceutical Company Ltd.

• HINO Katsuhiko

  Discovery Research Laboratories II, Dainippon Pharmaceutical Company, Ltd.,

• Fujita M

  Vlsi Design And Education Center (vdec) The University Of Tokyo

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