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

ABSTRACT

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 H[2]SO[4]. 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 [1]H-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