Sequential analysis for identification of byproduct from N-benzylation reaction: wound healing and anti-inflammatory potential of the byproduct 4-chlorobenzyl 2-((4-chlorobenzyl)amino)benzoate

Abstract

A very common reaction, N-benzylation of isatoic anhydride in the presence of sodium hydride base, produces byproducts. The yield of one of the byproducts was greater than that of the desired product; therefore, we identified the anonymous undisclosed structure of the byproduct using sequential spectroscopy methods and SC-XRD. This byproduct was found to be effective as a wound-healing and anti-inflammatory agent. The 10% formulation of byproduct and standard (nitrofurazone) showed complete wound closure with a large number of cell migrations within 16 days. Hydroxyproline contents of 5% and 10% formulations were found to be slightly increased as compared with that of the standard. The byproduct also had anti-inflammatory potential. It was effective in inhibiting COX-2, heat-induced albumin denaturation, and formalin-induced paw edema.