Synthesis and Biological Evaluation of 1,2,4-Triazoles and 1,3,4-Oxadiazoles Derivatives Linked to 1,4-Dihydropyridines Scaffold

Abstract

A series of diethyl-2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate derivative coupled to 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones moieties at C2,C6 positions of 1,4-dihydropyridine ring system was prepared. This linkage was carried out by the reaction of 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones with 2,6-dibromomethyl-3,5-diethoxycarbonyl-4-phenyl-1,4-dihydropyridine in the presence of potassium carbonate as a weak base and dry acetone as the solvent. The newly synthesized compounds were characterized by FT-IR, 1 H NMR, 13 C NMR spectral data, elemental analysis and FAB-MS. The synthesized compounds were tested for their antimicrobial and antifungal activity against Escherichia coli and Aspergillus fumigatus in vitro in comparison with Enrofloxacin and Amphotericin as the reference drugs which are normally used for treating such infections. The synthetic compounds showed different inhibition zones against tested bacteria and fungi. Compound 8d showed more antagonistic activity against E. coli and A. fumigatus.

Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

“…Schiff bases of triazolethiones [40] have played vital roles in organic synthesis and they are obtained from triazolethiones using simple procedures; also, sometimes their structures possess biological and pharmaceutical activities other than triazolethione itself such as anti-inflammatory and anti-oxidant [41], anticancer [42], fungicidal activities [43], antibacterial [44], antiparasitic [45], antidepressant and antimicrobial [46]. Furthermore, many transition metal complexes of 1,2,4-triazolethione Schiff bases and their bioactivities were reported [47][48][49] along with nickel complexes of triazolethiones [50] showing high catalytic activity towards the synthesis of tetrahydrobenzo[b]pyrans [47].…”

Efficient One-Pot Synthesis of 1,4-Dihydropyridines Catalyzed by Magnetic MnFe2O4 Nanoparticles

“…7 The Hantzsch reaction is a practical and useful synthetic tool for the preparation of 1,4-dihydropyridines by condensation of ethyl acetoacetate, an aldehyde, and a source of ammonia in the presence of an Moradi et al: Efficient One-Pot Synthesis of 1,4-Dihydropyridines ... alcoholic solvent. 8 In modern synthetic organic chemistry, 1,4-dihydropyridines are an important group of drugs [9][10][11] and calcium channel modulators for the treatment of hypertension, 1 2 tumors, 13,14 HIV, 15 cancer, 16 diabetes, 17 apoptosis, and 18 seizures. 19 For example, nifedipine (1), felodipine (2), diludin (3), amlodipine (4), nicardipine (5), nisodipine (6), and nimodipine (7) are synthesized and used worldwide (Figure 1).…”

Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

“…In our previous study, we reported the synthesis and antimicrobial assessment of 1,4-dihydropyridines with azole derivatives in the C2 and C6 positions of DHP ring. 22 Based on the abovementioned gap in the related literature, the present study focuses on synthesizing the novel 1,4-dihydropyridine derivative, which are linked to triazole and oxadiazole moieties, and evaluating their cytotoxic activities.…”