Synthesis and characterization of a novel series of 1,4-dihydropyridine analogues for larvicidal activity against Anopheles arabiensis

DHARMA RAO, BHASKARA D.; BHANDARY, SUBHRAJYOTI; CHOPRA, DEEPAK; VENUGOPALA, KATHARIGATTA N.; GLEISER, RAQUEL M.; KASUMBWE, KABANGE; ODHAV, BHARTI

CHEMICAL BIOLOGY & DRUG DESIGN

WILEY-BLACKWELL PUBLISHING, INC

Año: 2017 vol. 90 p. 397 - 405

1747-0277

The new-fangled bis(4-substituted benzyl) 4-(4-substitued phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate derivatives were synthesized by the union of substituted aryl aldehyde, tert-butyl acetoacetate, ammonium carbonate with 4-substituted benzyl alcohol via Hantzsch ester synthesis in aqueous medium under catalyst-free conditions. The newly synthesized compounds were characterized by spectroscopic techniques such as IR, NMR (1H and 13C), ESI mass, elemental analysis, and single-crystal X-ray diffraction. The characterized title compounds were evaluated for the larvicidal activity against Anopheles arabiensis by standard WHO larvicidal assay method using Temephos as standard at 4 μg/ml. The title compounds bis(4-methoxybenzyl) 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and bis(4-chlorobenzyl) 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate exhibited promising larvicidal activity at 65.6% and 72.2%, respectively, when compared with the standard compound at 98.9%.