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

• Published in: RSC advances Vol. 13; no. 37; pp. 25904 - 25911
• Main Authors: Verma, Ekta, Patil, Shailendra, Gajbhiye, Asmita
• Format: Journal Article
• Language: English
• Published: Cambridge Royal Society of Chemistry 29-08-2023; The Royal Society of Chemistry
• Subjects: Benzoates; Byproducts; Chemistry; Denaturation; Edema; Sequential analysis; Sodium hydrides; Wound healing
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/d3ra03720g

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.