Synthesis And Characterization Of Oxime-Linked Arylacetamide Derivative Of Benzo[f]Coumarins As Potential Anti-Proliferative Agent

Abstract

Coumarin derivatives are pharmacologically active compounds and are used as potential drug candidates. Several coumarin hybrids act as FDA approved drugs. In the present work, aryl acetamide derivatives of benzo[f]coumarins linked via oxime functionality were synthesized using multistep convergent synthesis with the aim to exhibit anti-proliferative activities. In the synthesis of the target molecule, 2-hydroxy naphthaldehyde (I) was used as a starting material, that was converted into 2-acetyl 3H-benzo[f]chromen-3-one (III) by the reaction of2-hydroxy naphthaldehyde (I) with ethyl acetoacetate (II). 2-Acetyl-3H-benzo[f]chromen-3-one (III) was converted to 2- (1-Hydroxyimino)ethyl)-3H-benzo[f]chromen-3-one (IV) by the oximation of its 3-oxo group. Subsequently, 2-chloro-N-aryl acetamides (VIIa-o) were prepared from differently substituted anilines and 2-chloroacetyl chloride (VI). Finally, 2-(1- hydroxyimino )ethyl)-3H-benzo[f]chromen-3-one (IV) was coupled with 2-chloro-N aryl acetamide (VIIa-o) derivatives to afford the target molecule (VIlla-o). All the synthesized compounds (VIIIa-o) were characterized using FT-IR, IH and 13C_ NMR spectroscopy. The synthesized compounds (VIIIa-o) will be further confirmed by using GC-MS/LC-MS and XRD (where applicable) analysis, and will be evaluated against various cancer cell lines.