Construction of 3-oxo-3H-spiro[benzofuran-2,1'-cyclopentane] carboxylic acid derivatives via phosphine-catalyzed [4 + 1] annulations and their biological evaluation against fibrosis

  • Bioorg Med Chem. 2025 Jul 1:124:118192. doi: 10.1016/j.bmc.2025.118192.
Sheng-Hong Li  1 ,  Feng-Yi Lu  1 ,  Muralikrishna Katta  1 ,  Yun-Yun Liu  1 ,  Danling Huang  2 ,  Yong-Xian Cheng  3
Affiliations
  • 1. Institute for Inheritance-Based Innovation of Chinese Medicine, Guangdong Provincial Key Laboratory of Chinese Medicine Ingredients and Gut Microbiomics, School of Pharmacy, Shenzhen University Medical School, Shenzhen 518060, PR China.
  • 2. Institute for Inheritance-Based Innovation of Chinese Medicine, Guangdong Provincial Key Laboratory of Chinese Medicine Ingredients and Gut Microbiomics, School of Pharmacy, Shenzhen University Medical School, Shenzhen 518060, PR China. Electronic address: [email protected].
  • 3. Institute for Inheritance-Based Innovation of Chinese Medicine, Guangdong Provincial Key Laboratory of Chinese Medicine Ingredients and Gut Microbiomics, School of Pharmacy, Shenzhen University Medical School, Shenzhen 518060, PR China. Electronic address: [email protected].
PMID: 40252564 DOI: 10.1016/j.bmc.2025.118192
Abstract

A novel phosphine-catalyzed [4 + 1] cyclization reaction was developed to construct the 3-oxo-3H-spiro[benzofuran-2,1'-cyclopentane] scaffold. Utilizing this innovative method, twenty diverse 3-oxo-3H-spiro[benzofuran-2,1'-cyclopentane] carboxylic acid derivatives were synthesized and evaluated for their anti-fibrotic activities. Compound L10-P1 possessed potential anti-fibrotic activity by inhibiting the expression of fibronectin, Collagen I, and α-SMA. This study presents a new synthetic route for 3H-spiro[benzofuran-2,1'-cyclopentan]-3-one derivatives, contributing valuable insights into the chemical and biological diversity of these compounds.

Keywords
Anti-fibrotic activity; Spirocyclic benzofuranones; [4+1] Cyclization.
Products