Synthesis of 5-O-4-Chlorobenzoylpinostrobin as a New Anti-Inflammatory Drug Candidate
نویسندگان
1 Department of Pharmaceutical Sciences, Faculty of Pharmacy, Airlangga University, Campus C Unair, Mulyorejo, Surabaya 60115, Indonesia
2 Diploma III Study Program of Pharmaceutical and Food Analysis, Faculty of Pharmacy, Institut Ilmu Kesehatan Bhakti Wiyata, Kediri 64114, Indonesia
3 National Research and Innovation Agency, CPOTB Building KST BJ Habibie, Puspitek Setu Serpong Area, Muncul, Setu District, South Tangerang City, Banten 15314, Indonesia
4 Faculty of Pharmacy, Institut Ilmu Kesehatan Bhakti Wiyata, Kediri 64114, Indonesia
5 Diploma III Study Program of Pharmaceutical and Food Analysis, Faculty of Pharmacy, Institut Ilmu Kesehatan Bhakti Wiyata, Kediri 64114, Indonesia
6 Research Center for Computing, Research Organization of Electronics and Informatics, National Research and Innovation Agency (BRIN), Soekarno Science & Technology Park, Cibinong - Bogor, Km. 46, West Java, Indonesia
7 Research Center for Computing, Research Organization of Electronics and Informatics, National Research and Innovation Agency (BRIN), Soekarno Science & Technology Park, Cibinong - Bogor, Km. 46, West Java, Indonesia
doi
10.48309/AJGC.2025.516007.1726چکیده
Background and Objective: The rhizome of temu kunci (Boesenbergia pandurata Roxb.) contains pinostrobin (5-hydroxy-7-methoxyflavanone), which is acknowledged for its anti-inflammatory properties. This study aims to predict the anti-inflammatory activity of 5-O-4-Chlorobenzoylpinostrobin in silico and to synthesize the target compound from pinostrobin derivatives. Method: Pinostrobin, isolated from temu kunci, was modified with 4-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 5-O-4-Chlorobenzoylpinostrobin exhibits stronger anti-inflammatory activity than pinostrobin by inhibiting the COX-2 receptor. FTIR analysis indicated the formation of a C=O ester group and the disappearance of the -OH group at C5. 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 5-O-4-Chlorobenzoylpinostrobin has promising anti-inflammatory activity. The synthesis was successfully validated by spectroscopic and spectrometric analysis, confirming the formation of a novel compound.
