Design, synthesis, and characterization of (1-(4-aryl)-1<em>H</em>-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against <em>Mycobacterium tuberculosis</em>

Abstract

The novel (1-(4-aryl)-1H-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives were synthesized by the click reaction of the dihydropyrimidinones, bearing a terminal alkynyl group, with various substituted aryl azides at room temperature using a catalytic amount of Cu(OAc)2 and sodium ascorbate in a 1:2 ratio of acetone and water as a solvent. The newly synthesized compounds were characterized by a number of spectroscopic techniques, such as infrared, liquid chromatography-mass spectrometry, 1H, and 13C nuclear magnetic resonance along with single crystal X-ray diffraction. The current procedure for the synthesis of 1,2,3-triazole hybrids with dihydropyrimidinones is appropriate for the synthesis of a library of analogs 7a-l and the method accessible here is operationally simple and has excellent yields. The title compounds 7a-l were evaluated for their in vitro antitubercular activity against H37RV and multidrug-resistant strains of Mycobacterium tuberculosis by resazurin microplate assay plate method and it was found that compound 7d was promising against H37RV and multidrug-resistant strains of M. tuberculosis at 10 and 15 μg/mL, respectively.

Hantzsch Reaction: A Greener and Sustainable Approach to 1,4‐Dihydropyridines Using Non‐commercial β‐Ketoesters

“…As a part of our foregoing work and much endeavor over the years to develop an efficient synthetic procedures for multi‐component reactions under greener conditions , there was a requirement to construct a huge library of diversified 1,4‐dihydropyridine analogs with dropping time, outstanding yields, and exceptional biological activities. Initially, we examine the different common ammonium salts (nitrogen source) for the synthesis of 1,4‐dihydropyridine derivatives using non‐commercial β‐ketoesters that are generated by the reaction between tert ‐butylacetoacetate and corresponding alcohol via trans ‐esterification .…”

Synthesis, biological evaluation and molecular docking study of dihydropyrimidine derivatives as potential anticancer agents

“…The pyrimidine system is an important pharmacophore with abundant occurrence in nature. Natural and synthetic dihydropyrimidine derivatives have a wide range of pharmacological actions, such as antifungal, anticonvulsant, antitubercular, anti‐inflammatory, and antiviral . Several drugs have been developed from tetrahydropyrimidine derivatives like sildenafil, which is an inhibitor of phosphodiesterase.…”

Larvicidal study of tetrahydropyrimidine scaffolds against Anopheles arabiensis and structural insight by single crystal X‐ray studies

“…HPM molecules are generally synthesized by multicomponent reaction, which was discovered by Italian chemist Pietro Biginelli in 1893, known as Biginelli reaction, which is a simple combination of equal molar ratio of alkyl/aryl aldehyde, β‐keto ester, and urea or thiourea in the presence of acid as a catalyst in ethanol medium . Owing to hetero atom present on HPM scaffolds, these multicomponent products have shown various pharmacological properties such as antimicrobial, topoisomerase inhibitors, antimalarial, antitubercular, antimosquito, cardiovascular treatment as they act as potent calcium channel blockers, anti‐inflammatory, and pancreatic neuroendocrine neoplasm therapy . Copper complexes of HPM molecules are reported for the activity of human breast cancer cells .…”