Synthesis of Polyheterocyclic Compounds and Their Antioxidant Protein Binding and Anticancer Activities

Abstract

N-Heterocyclic compounds are common to bioactive compounds and synthetic newlinematerials. Herein, we have synthesized various N-heterocyclic compounds and newlineinvestigated their bioactivities. A series of N-cinnamoyl phenothiazine (N-CPTZ) were newlinesynthesized, and their protein and ct-DNA binding affinities were evaluated. Both newlineexperimental and molecular docking studies show 1:1 binding with bovine serum newlinealbumin (BSA) and an intercalative binding mode with ct-DNA. Antioxidant studies newlineshow N-cinnamoyl phenothiazine with nitro substituent exhibited better hydroxy and newlineDPPH radicals scavenging activity (EC50 = 77:8 and#956;M and 85:0 and#956;M) among the other newlineN-CPTZs investigated. For all derivatives (SKS2and#1048576;8 ), moderate activity was observed newlinetowards the four bacterial strains, while phenothiazine exhibited no inhibitory action newlineup to 500 and#956;m. This suggests that the N-cinnamoyl unit added could have induced the newlineobserved activity. newlineTo synthesize poly-N-heterocyclic compounds, quinolinyl-1,4-dihydropyridines, newlineand pyrrole fused benzoxazine derivatives, a highly regioselective base/Lewis newlineacid promoted synthetic protocol was developed. A one-pot multicomponent newlineapproach was adopted for the synthesis of quinolinyl-1,4-dihydropyridines. newlineTetrazoloquinoline-carbaldehyde, _-enamine and 3-oxo-3-phenylpropanenitrile newlinewere reacted in presence of triethylamine to obtain quinolinyl-1,4-dihydropyridines. newlineThe formation of the product was confirmed by various spectroscopic techniques, and newlinethe structure of one of the derivatives is established by single-crystal XRD. Three newlinecompounds, SKS13, 19 and 20 were found to be most active with IC50 value of newline7:87 and#956;M 9:55 and#956;M among the other compounds assessed for cytotoxic activity against newlinebreast cancer cell line, MCF7. To identify possible molecular targets, the highly active newlinemolecules were docked with various breast cancer targets. Docking score suggests newlinethat the active compounds possess multiple receptors targeting potential against breast newlinecancer. Our results support quinolinyl-1,4-dihydropyridines as an important scaffold to