Synthesis, molecular docking, antiproliferative and radical scavenging activities of vanillin derived 1,3,5-trisubstituted 2-pyrazolines

Abstract

Observing the good anticancer potential of 2-pyrazoline scaffold, a panel of 1,3,5- trisubstituted 2- pyrazolines namely, 5-(4-hydroxy-3-methoxyphenyl)-3-(4-substitutedphenyl)4,5-dihydro-1H-pyrazol-1 yl)(phenyl)methanones 2a-j and (5-(4-hydroxy-3-methoxyphenyl)-3-(4-substituted phenyl)4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanones 3a-j have been synthesized from the chalcone intermediates derived from the reaction between vanillin and substituted acetophenones, by condensing with benzhydrazide and isonicotinic acid hydrazide, respectively. The synthesized compounds have been characterized by spectral studies and screened for in vitro antiproliferative activity against human non small cell lung cancer cell line A549 by MTT assay and antioxidant activity by DPPH radical scavenging assay. The compound 2i has exhibited good antiproliferative activity followed by 2g and 2a. Compounds of both series 2a-j and 3a-j exhibited good radical scavenging activity. Molecular docking studies of 2h and 2j has revealed the good interaction with 3LCT (Crystal structure of anaplastic lymphoma kinase catalytic domain) receptor via hydrogen bonds, electrostatic and hydrophobic interactions. The drug-likeness properties of the compounds were also satisfactory leaving a good scope for further work.