The Synthesis and Characterization of New Asymmetrical Dihydropyridine Derivatives Containing a 2,4-Dichloro-5-Thiazolyl Substituent

Abstract

Dihydropyridines (DHP) having a heterocyclic aryl substituent at position-4 are calcium channel antagonists. In this report a new group of DHP derivatives with different esters at the C ₃ and C ₅ position (asymmetrical diesters) containing 2,4-dichloro-5-thiazolyl at position-4 were synthesized by a condensation reaction of alkyl, cycloalkyl, and aryl acetoacetate in the presence of ammonium acetate in a new shorter pathway. The structure of all compounds was confirmed by IR, ¹ H NMR, and mass spectrometry. The calcium channel antagonist activity of compounds 6a–6f demonstrated that the compound 6a was the most active compound.

Keywords:

• 1,4-dihydropyridines
• Ca²⁺-channel-antagonist
• heterocyclic compounds
• thiazole

Acknowledgments

This research was supported by grants from the research council of Tehran University of Medical Sciences and Iran National Science Foundation (INSF), Tehran, Iran.