Synthesis and anti-arrhythmic activity of some piperidine-based 1,3-thiazole, 1,3,4-thiadiazole, and 1,3-thiazolo[2,3-c]-1,2,4-triazole derivatives |
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Authors: | Hatem A Abdel-Aziz Bakr F Abdel-Wahab Marwa A M Sh El-Sharief Mohamed M Abdulla |
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Institution: | (1) Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo, Egypt;(2) Research Units, Hi-Care Pharmaceutical Co., Cairo, Egypt |
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Abstract: | Abstract The reaction of 1-4-(piperidin-1-yl)benzylidene]thiosemicarbazide with hydrazonoyl chlorides afforded 1,3-thiazole derivatives.
Cyclization of two compounds of the latter 1,3-thiazole by means of bromine in the presence of sodium acetate at room temperature
gave 1,3-thiazolo2,3-c]-1,2,4-triazole derivatives. The reaction of 2-cyano-3-(4-piperidin-1-ylphenyl)prop-2-enethioamide with hydrazonoyl chlorides
under reflux in ethanol in the presence of triethylamine yielded 1,3-thiazoles. Treatment of 3-oxo-3-(piperidin-1-yl)propanenitrile
with phenyl isothiocyanate in DMF, in the presence of KOH, at ambient temperature, resulted in the formation of 3-anilino-3-mercapto-2-(piperidin-1-ylcarbonyl)acrylonitrile
which was reacted with hydrazonoyl chlorides to yield the corresponding 1,3,4-thiadiazole derivatives. Some of the newly synthesized
compounds had significant anti-arrhythmic activity.
Graphical Abstract
![MediaObjects/706_2008_53_Figa_HTML.gif](/content/v271370u6860x178/MediaObjects/706_2008_53_Figa_HTML.gif) |
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Keywords: | Heterocycles Cyclizations 1 3-Thiazole 1 3 4-Thiadiazole Anti-arrhythmic activity |
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