A Stereospecific Synthesis and In Vitro Anti-Influenza H1N1 Properties of Lithocholic Acid-Based <i>Spiro</i>-1,2,4-trioxolane.

ABSTRACT: Bile acids provide a versatile platform for the design of biologically active compounds due to their amphiphilic structure, biocompatibility, and capacity for diverse chemical modifications. Among them, lithocholic acid is a promising scaffold for designing and revealing new antiviral agents. A novel lithocholic acid-based 3-spiro-1,2,4-trioxolane was synthesized by Griesbaum co-ozonolysis of methyl 3-O-methyl-oximino-lithocholate and 4-(trifluoromethyl)-cyclohexanone, and its structure was confirmed by 2D NMR and X-ray crystallographic analysis. Lithocholic acid derivatives were evaluated for cytotoxicity and anti-influenza activity against A/Puerto Rico/8/34 (H1N1), showing that steroid 1,2,4-trioxolane 3 exhibited the highest potency (IC₅₀ 4.3 µM, SI 11)

SUBMITTER: Smirnova I 

PROVIDER: S-EPMC12693687 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature