YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Syntheses of Nitrogen-containing Heterocyclic Compounds. XXXII. On the Antimicrobial Activity of Diazaphenanthrenes and Syntheses of Triazaphenanthrenes related to Nalidixic Acid
ISAO TAKEUCHIISAO OZAWATOSHIRO OGAKIYOSHIKI HAMADATOMIYOSHI ITO
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1978 Volume 98 Issue 9 Pages 1279-1285

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Abstract

2-Aminoquinoline and 3-amino-1, 8-naphthyridine (XI) were cyclized by ethoxy methylenemalonate and both afforded an angular type products (II and XIII). Hydrolysis of II, ethyl 4-hydroxy-5-methyl-1, 6-phenanthroline-3-carboxylate, and XIII gave 2-aminoquinoline from II and carboxylic acid derivatives (III and XIV) from the others. N-Alkylation of III, ethyl carboxylate of III, and XIV gave IV, VII, and XV. The active methylene group in XVI was oxidized with selenium dioxide to the aldehyde derivative (XVII) and XVII was oxidized with hydrogen peroxide to obtain a carboxylic acid derivative (XVIII). Antibacterial test of the synthesized compounds, III to VII, XV to XVIII, and diazaphenanthrenes (XIX to XXXIII) indicated that these compounds have a slightly strong antibacterial activity against Pseudomonas aeruginosa.

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© by the PHARMACEUTICAL SOCIETY OF JAPAN
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