Synthesis, characterization and enzyme inhibition study of O-substituted derivatives of chlorinated coumarin

Coumarins have much importance in dyes, drugs, perfumes and pesticides. In the demonstrated research work, a benignant series of chlorinated coumarins was synthesized and screened against different enzymes. First, 6-Chloro-7- hydroxy-4-methyl-2H-chromen-2-one (3) was geared up by the reaction of 4-chlororesorcinol (1) and ethyl acetoacetate (2) in the presence of concentrated H2SO4. Second, various O-substituted derivatives of chlorinated coumarins, 5a-j, were set up by pairing different alkyl/aralkyl halides, 4a-j, with 3 in the presence of NaH in DMF as solvent. The structures of all the synthesized compounds were clarified through spectral analysis using EI-MS, IR and 1H-NMR. The different enzymes used for the evaluation of bioactivity of all the synthesized compounds were acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase (LOX). The most proficient activity was shown against both cholinesterase enzymes.