Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1-b]Thiazole Moiety

合成及含咪唑并[2,1-b]噻唑部分的新型肼基硫代甲酰胺和4-噻唑烷酮的醛糖还原酶抑制作用

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Abstract

OBJECTIVES: To synthesize and characterize 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-alkyl/arylhydrazinecarbothioamide and 3-alkyl/aryl-2-[((6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl)acetyl)hydrazono]-5-nonsubstituted/methyl-4-thiazolidinone derivatives and evaluate them for their aldose reductase (AR) inhibitory effect. MATERIALS AND METHODS: 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-alkyl/arylhydrazinecarbothioamides (3a-f) and 3-alkyl/aryl-2-[((6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl)acetyl)hydrazono]-5-nonsubstituted/methyl-4-thiazolidinones (4a-j) were synthesized from 2-[6-(4-bromophenyl)imidazo[2,1-b]thiazole-3-yl]acetohydrazide (2). Their structures were elucidated by elemental analyses and spectroscopic data. The synthesized compounds were tested for their ability to inhibit rat kidney AR. RESULTS: Among the synthesized compounds, 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-benzoylhydrazinecarbothioamide (3d) showed the best AR inhibitory activity. CONCLUSION: The findings of this study indicate that the different derivatives of the compounds in this study may be considered interesting candidates for future research.

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