結核菌に対する化学療法剤の研究 (第18報)

2-Salicylidenehydrazono-4-thiazolidinone関連化合物の合成および抗菌作用 その9

抄録

2-Salicylidenehydrazono-4-thiazolidinone (I) and its 5-methylated derivative (II) possess strong anti-tubercular activity but have small solubility. Its derivative (III) substituted with a methyl in the position alpha to salicylidene group, prepared in order to increase the solubility, was found to have lost the anti-tubercular action. In the present series of work, derivatives of (III) possessing hydroxyl or methoxyl in the benzene ring were prepared in the form of 2-(2, 4(or 5)-dihydroxy-α-methyl-benzylidenehydrazono)-4-thiazolidinone and its 5-methyl derivative, and 2-(2-hydroxy-4(or 5)methoxy-α-methylbenzylidenehydrazono)-4-thiazolidinone and its 5-methyl derivative were prepared and submitted to antibacterial tests. It was thereby found that 4- or 5-methylated derivatives of the latter possessed antibacterial activity close to that of (I) or (II).
The preparation of these derivatives was made by the reaction of dihydroxyacetophenone and its monomethyl ether with thiosemicarbazide to form the corresponding thiosemicarbazones which were condensed with ethyl monochloroacetate or α-bromo-propionate, in the presence of sodium acetate.