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  3. Benzenoid ring C-H olefination of Coumarins under Rh(III)-catalysis: Synthesis, anti-inflammatory evaluation and in silico studies

Benzenoid ring C-H olefination of Coumarins under Rh(III)-catalysis: Synthesis, anti-inflammatory evaluation and in silico studies

  • Bioorg Chem. 2026 Apr:171:109553. doi: 10.1016/j.bioorg.2026.109553.
Amardeep Singh 1,  Manjeet Chopra 2,  Archit Mukherjee 3,  Akshay Kamble 4,  Alok Jain 5,  Hemant Kumar 6,  Satyasheel Sharma 7
Affiliations

Affiliations

  • 1 Department of Natural Products, National Institute of Pharmaceutical Education and Research, Ahmedabad (NIPER-A), Gandhinagar, Gujarat 382355, India.
  • 2 Department of Pharmacology, National Institute of Pharmaceutical Education and Research, Ahmedabad (NIPER-A), Gandhinagar, Gujarat 382355, India.
  • 3 Advanced BioComputing Lab, Department of Bioengineering and Biotechnology, Birla Institute of Technology Mesra, Ranchi 835215, Jharkhand, India.
  • 4 Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Ahmedabad (NIPER-A), Gandhinagar, Gujarat 382355, India.
  • 5 Advanced BioComputing Lab, Department of Bioengineering and Biotechnology, Birla Institute of Technology Mesra, Ranchi 835215, Jharkhand, India. Electronic address: alokjain@bitmesra.ac.in.
  • 6 Department of Pharmacology, National Institute of Pharmaceutical Education and Research, Ahmedabad (NIPER-A), Gandhinagar, Gujarat 382355, India. Electronic address: hemant@niperahm.res.in.
  • 7 Department of Natural Products, National Institute of Pharmaceutical Education and Research, Ahmedabad (NIPER-A), Gandhinagar, Gujarat 382355, India; Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Ahmedabad (NIPER-A), Gandhinagar, Gujarat 382355, India. Electronic address: satyasheel.sharma@niperahm.res.in.
PMID: 41619438 DOI: 10.1016/j.bioorg.2026.109553
Abstract

The C-H functionalization of coumarin benzenoid ring has been underexplored. In this study, we have carried out the Rh(III)-catalyzed C-H olefination on the benzenoid ring of coumarin at C8 and C6 position using O-carbamate directing group. The method is successfully applied to diverse range of Coumarins and acrylates. Further, we have evaluated the synthesized compounds for their anti-inflammatory activity against tumor necrosis factor-alpha production in LPS-stimulated RAW264.7 macrophage cell line. Among the synthesized olefinated coumarin compounds, 4ea and 3ag were able to exhibit potent TNF-α expression inhibition, with IC50 values of 6.297 μM and 11.87 μM, respectively. Further, compound 4ea was also found to inhibit the NF-kB expression. In addition, the interaction of the most potent compound 4ea with TNF-α dimer (PDB ID: 2AZ5) was elucidated by molecular docking and molecular simulation studies.

Keywords

Anti-inflammatory; Carbamates; Coumarin; C–H Functionalization; Olefination; TNF-α.

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