Synthesis and Antitubercular Activity of 2‐(substituted phenyl/benzyl‐amino)‐6‐(4‐chlorophenyl)‐5‐(methoxycarbonyl)‐4‐methyl‐3,6‐dihydropyrimidin‐1‐ium Chlorides

Abstract

A series of 2-(substituted phenyl/benzyl-amino)-6-(4-chlorophenyl)-5-(methoxycarbonyl)-4-methyl-3,6-dihydropyrimidin-1-ium chlorides 7-13 and 15 was synthesized in their hydrochloride salt form. The title compounds were characterized by FT-IR, NMR ((1)H and (13)C) and elemental analysis. They were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv, multidrug resistance tuberculosis and extensively drug resistance tuberculosis by agar diffusion method and tested for the cytotoxic action on peripheral blood mononuclear cells by MTT assay. Among all the tested compounds in the series, compounds 7 and 11 emerged as promising antitubercular agents at 16 μg/mL against multidrug resistance tuberculosis and over 64 μg/mL against extensively drug resistance tuberculosis. The conformational features and supramolecular assembly of the promising compounds 7 and 11 were determined by single crystal X-ray study.

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>

“…As a continuing aspect of our earlier work6,37,51 and after much efforts over the years to develop efficient synthetic procedures for multicomponent reactions under greener conditions, there was a requirement to synthesize a huge library of diversified 1,2,3-triazole hybrids with DHPMs analogs with reduced time, outstanding yields, and excellent biological activities. The DHPMs with terminal alkynyl group were synthesized following a previously reported procedure 52.…”

“…In this communication and in continuation of our work on the development of pharmacologically active heterocyclic compounds6,34,35 and screening of heterocyclic compounds for properties of polymorphism,36–38 we have synthesized 1,2,3-triazole hybrid with DHPMs using aryl azide as well as DHPMs having a terminal alkynyl group, which was synthesized by the four component Biginelli-like cyclocondensation reaction ( tert -butyl β-ketoester, propargyl alcohol, aryl aldehyde, and urea) along with catalytic amount of Cu(OAc) 2 and sodium ascorbate in a 1:2 ratio of acetone and water as a solvent at room temperature as shown in Figure 1.…”

“…Natural and synthetic dihydropyrimidine derivatives have a wide range of pharmacological actions, such as anticancer,1 antiviral,2,3 antihypertensive,4 calcium channel blocking,5 antitubercular,6 antimicrobial,7,8 anti-inflammatory,9,10 and larvicidal and insecticide actions 11,12. 1,2,3-Triazoles, as a vital class of N -heterocyclic compounds, due to their unique chemical and structural properties, have received a great deal of attention over the past few decades and found broad application in medicinal chemistry13 and particularly as anticancer,14 antimicrobial,15 antitubercular,16 anti-HIV,17 and antifungal agents 18.…”

Heteroannelation of Cyclic Ketones: Synthesis, Characterization and Antitumor Evaluation of Some Condensed Azine Derivatives

“…The azines have been reported to have antibacterial, 1,2 analgesic, 3 antitubercular, 4,5 anti-inflammatory, 6,7 antioxidant, 8,9 and antiviral activities. 11-14 2-Oxo-1,2-dihydropyridine-3-carbonitrile derivatives were reported as inhibitors of the oncogenic serine/threonine kinase 15,16 and for the treatment of the congestive heart failure.…”

“…Furthermore, reaction of 2,6-bis(2-methoxybenzylidene)cyclohexanone (6) with different cyano nucleophiles yielded chromene and quinoline derivatives of promising antitumor activity.…”