1969 年 89 巻 8 号 p. 1119-1124
Forty-two kinds of compounds mainly related to 3-methoxy-4-phenoxybenzaldehyde thiosemicarbazone and 22 kinds of compounds similar to its demethylated compound, 3-hydroxy-4-phenoxybenzaldehyde, were synthesized and their antibacterial action against human tubercle bacilli, H37Rv sensitive strain, was tested, using a Tween-albumin medium. Against the control growth-inhibitory values of 0.0313 μg/ml for isonicotinoyl hydrazide (INH) and 0.625 μg/ml for tibione (TBI), 3-methoxy-4-phenoxybenzaldehyde (p-tolyl) thiosemicarbazone and 4-(o-methoxyphenyl) thiosemicarbazone showed the value of 3.13 μg/ml, and 4-allyl-, 4-propyl-, 4-butyl-, 4-(p-methoxyphenyl)-, 4-(o-ethoxyphenyl)-, and 4-(p-iso-butoxyphenyl)-thiosemicarbazones and amidinohydrazone hydrochloride all showed growth inhibition in a concentration of 6.25 μg/ml. 3-Hydroxy-4-phenoxybenzaldehyde derivatives all failed to show any antibacterial activity and this fact indicated that the presence of a methoxyl group was significant in the appearance of antibacterial activity against this strain of tubercle bacilli. 3-Methoxy-4-phenoxybenzaldehyde isonicotinoylhydrazone inhibited the growth of tubercle bacilli at a concentration of 0.078 μg/ml, but it was found to have cross-resistance with INH.