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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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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-thiazolo[2,3-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.

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Authors and Affiliations

  1. Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo, Egypt

    Hatem A. Abdel-Aziz, Bakr F. Abdel-Wahab & Marwa A. M. Sh. El-Sharief

  2. Research Units, Hi-Care Pharmaceutical Co., Cairo, Egypt

    Mohamed M. Abdulla

Authors
  1. Hatem A. Abdel-Aziz
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  2. Bakr F. Abdel-Wahab
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  3. Marwa A. M. Sh. El-Sharief
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  4. Mohamed M. Abdulla
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Corresponding author

Correspondence to Marwa A. M. Sh. El-Sharief.

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Abdel-Aziz, H.A., Abdel-Wahab, B.F., El-Sharief, M.A.M.S. et al. 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. Monatsh Chem 140, 431–437 (2009). https://doi.org/10.1007/s00706-008-0053-y

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