アンチピリン誘導体の合成および抗菌性 (第4報)

チアゾール系化合物 その1

抄録

A total of 36 kinds of new antipyrine derivatives were synthesized, including 3 kinds of 2-(4-antipyrinylamino)thiazoles (II to IV), 18 kinds of 4-(4-antipyrinyl)thiazoles (VI to XXIII), 5 kinds of 2-(4-antipyrinylamino)-4-(4-antipyrinyl)thiazoles (XXIV to XXVIII), two kinds of 2-(4-antipyrinyl)methylenehydrazinothiazoles (XXIX and XXXI), 3 kinds of 4-(4-antipyrinyl)-2-arylidenehydrazinothiazoles (XXXVII to XXXIX), two kinds of 2-(2-methyl-1-phenyl-5-pyrazolon-4-yl)methylmethylenehydrazinothiazoles (XXXIII and XXXIV), 2-(4-antipyrinyl)methylmethylenehydrazino-4-phenylthiazole (XXXVI), and the starting materials, 4-acetylantipyrine thiosemicarbazone (XXXV), and 1-phenyl-4-acetyl-2-methyl-5-pyrazolone thiosemicarbazone (XXXII), as well as the known 4-(4-antipyrinyl)-2-aminothiazole (V) and 2-(4-antipyrinyl)methylenehydrazino-4-phenylthiazole (XXX). Antibacterial test of these compounds using tubercle bacilli, Staphylococcus aureus, and Escherichia coli showed that compounds having arylidenehydrazino group (XXXIX, XXX, XXXVII to XXXIX, XXXIII, XXXIV, XXXVI) and the starting thiosemicarbazones (XXXV and XXXII) had weak activity against tubercle bacilli. With the gram-positive Staphylococcus aureus, 4-(4-antipyrinyl)-2-salicylidenehydrazinothiazole (XXXVIII) showed growth-inhibitory action at 160, 000 dilution (6.25γ/cc.). Antibacterial action of (XXXVIII) against other gram-positive bacteria such as Bacillus subtilis, Diplococcus pneumoniae, Streptococcus hemolyticus, Cl. tetanii, and Cl. perfrigens, showed that the compound had inhibitory action against D. pneumoniae in 6.25γ/cc. concentration and a weak activity against Strept. hemolyticus but was ineffective to all other bacteria. None of the compounds proved effective against the gram-negative coli bacilli.