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

5 years ago

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

Kabange Kasumbwe, Raquel M. Gleiser, Deepak Chopra, Subhrajyoti Bhandary, Bharti Odhav, Katharigatta N. Venugopala, Bhaskara D. Dharma Rao

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%. The title compounds were synthesized by a one-pot multi-component Hantzsch ester synthesis in aqueous medium under catalyst-free conditions. Larvicidal results revealed that the presence of different substituents, namely nitro, chloro, and methoxy groups, influenced the larvicidal activity when compared to the standard compound. A promising larvicidal compound from the series has been characterized using single crystal X-ray diffraction.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1111/cbdd.12957