Work

Synthesis, NMR and X-ray characterization of dibenzoannulated dimeric steroid spiroketals. Evaluation of cytotoxicity and anti-inflammatory activity

Year: 2025

Type: article

Abstract: • Two dibenzoannulated dimeric steroid spiroketals were obtained. • NMR experiments provided enough evidence on the obtained structures. • X-Ray Diffraction corroborated the proposed structures. • The dimers obtained show potential anti-inflammatory activity. Two dibenzoannulated dimeric steroid spiroketals were obtained from cholesterol and 1,4-phenylenedimethanol. The key step in synthetic protocol is a Pd-catalyzed double spiroketalization in an adduct obtained from the double Sonogashira coupling of the 5α and 5β diastereomers of 4,5-secocholestan-5-ol. A detailed NMR characterization supported by Single Crystal X-ray Diffraction studies corroborated the obtained structures. While no cytotoxic effect was observed, the obtained compounds produced a significant reduction in the production of nitric oxide in macrophages stimulated with Lipopolysaccharide (LPS), indicating a potential anti-inflammatory activity.

Source: Steroids

DOI: 10.1016/j.steroids.2025.109614