Syntheses and Antimicrobial Activities of N-Heterocyclic-β-mercaptocinnamamides and Related Compounds

概要

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In order to obtain useful antimicrobial compounds, a number of N-heterocyclic-β-mercaptocinnamamides (IIIa-i) and related compounds were prepared. N-Heterocyclic phenylpropiolamides (I) were obtained by the reaction of heterocyclic amines with phenylpropioloyl chloride. The addition of thiourea to I gave the isothiuronium salts (II), which were converted into the mercapto compounds (III) with aqueous sodium hydroxide. In the reaction of 2-aminothiazole or 2-amino-4-methylthiazole with phenylpropioloyl chloride in the presence of triethylamine, thiazolo [3,2-α] pyrimidines (V, VII and VIII) were given together with the expected amides (If and Ig). The hydrolysis of S-[2-(3-methyl-1-phenyl-5-pyrazolyl) carbamoyl-1-phenylvinyl]-isothiourea p-toluenesulfonate (IIe) with aqueous sodium hydroxide at 90° gave 6,7-dihydro-1,4-diphenyl-3-methyl-6-oxopyrazolo [3,4-b] pyridine (IX) and a small amount of the mercapto compound (IIIe). Acyl migration from S to N was found in the acylthio derivatives of N-(2-thiazolyl)-(IIIf) and N-(4-methyl-2-thiazolyl)-β-mercaptocinnamamide (IIIg). Most of the compounds synthesized were considerably active in vitro against various gram-positive bacteria and fungi. However, only three of them were effective against Trichophyton in the in vivo tests.
公益社団法人日本薬学会の論文
1972-08-25