Synthesis of ۵-O-۴-Chlorobenzoylpinostrobin as a New Anti-Inflammatory Drug Candidate

Background and Objective: The rhizome of temu kunci (Boesenbergia pandurata Roxb.) contains pinostrobin (۵-hydroxy-۷-methoxyflavanone), which is acknowledged for its anti-inflammatory properties. This study aims to predict the anti-inflammatory activity of ۵-O-۴-Chlorobenzoylpinostrobin in silico and to synthesize the target compound from pinostrobin derivatives. Method: Pinostrobin, isolated from temu kunci, was modified with ۴-chlorobenzoyl chloride to enhance its activity. The compound was evaluated using in silico docking studies and synthesized via a modified Schotten–Baumann method under microwave irradiation. The structure was confirmed through UV-Vis spectroscopy, FTIR, ¹H-NMR, ¹³C-NMR, and LC-HRMS analyses. Results: Molecular docking using AutoDockTools predicted that ۵-O-۴-Chlorobenzoylpinostrobin exhibits stronger anti-inflammatory activity than pinostrobin by inhibiting the COX-۲ receptor. FTIR analysis indicated the formation of a C=O ester group and the disappearance of the -OH group at C۵. In the ¹H-NMR spectrum, the absence of aromatic protons suggested successful substitution. The ¹³C-NMR spectrum showed five peaks in the downfield region, confirming structural changes. LC-HRMS results matched the theoretical molecular weight of the synthesized compound. Conclusion: The in-silico study suggests that ۵-O-۴-Chlorobenzoylpinostrobin has promising anti-inflammatory activity. The synthesis was successfully validated by spectroscopic and spectrometric analysis, confirming the formation of a novel compound.

کلیدواژه ها:

anti-inflammatory activity ، ۵-O-۴-Chlorobenzoylpinostrobin ، In silico study ، Pinostrobin ، Chemical synthesis