Synthesis of Benzannulated Spiroketals Derived From Stigmasterol and Sitosterol by Pd‐Catalyzed Spirocyclization. NMR and X‐ray Characterization. Evaluation of Cytotoxicity and Anti‐Inflammatory Activity
ABSTRACT Five new benzannulated steroid spiroketals were synthesized by Pd‐catalyzed spiroketalization of 5α and 5β‐alkynediols derived from stigmasterol and sitosterol. The detailed nuclear magnetic resonance (NMR) and X‐ray characterization of the newly obtained spiroketals are presented. While the obtained compounds showed null or very low cytotoxicity, two of them inhibited more than 60% of the nitrous oxide production in J774A.1 macrophages stimulated with LPS, showing promising properties as anti‐inflammatory agents.
Authors
- Martín A. Iglesias‐Arteaga (ORCID: https://orcid.org/0000-0003-4764-7664)
- Marcos Flores-Ãlamo (ORCID: https://orcid.org/0000-0002-2996-7616)
- Martha C. Mayorquín‐Torres (ORCID: https://orcid.org/0000-0002-2338-9755)
- William H. García‐Santos (ORCID: https://orcid.org/0000-0002-6981-2424)
- Nimsi Campos‐Xolalpa (ORCID: https://orcid.org/0000-0002-5499-5432)
- Salud Pérez‐Gutiérrez (ORCID: https://orcid.org/0000-0002-3152-4283)
Institutions
- Universidad Autónoma de la Ciudad de México (MX)
- Universidad Autónoma Metropolitana (MX)
- Universidad Nacional Autónoma de México (MX)
Publication Details
- Journal
- Journal of Heterocyclic Chemistry
- Published
- 2024-10-02
- DOI
- https://doi.org/10.1002/jhet.4900
- Citations
- 1
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México