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![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
22-Oxocholestane oximes as potential anti-inflammatory drug candidates
Reyna Zeferino-Díaz1, Leticia Olivera-Castillo2, Alberto Dávalos3
1Departamento de Fisica Aplicada, Centro de Investigacion y de Estudios Avanzados, Unidad Merida, Km 6 Antigua Carretera a Progreso. Apdo. Postal 73, Cordemex, 97310, Merida, Yuc., Mexico; Facultad de Ciencias Quimicas, Benemerita Universidad Autonoma de Puebla, Ciudad Universitaria, 72570, Puebla, Pue., Mexico.
Abstract:
22-Oxocholestanes bearing the oxime functionality in the side chain have been synthesized from diosgenin and evaluated in vivo as anti-inflammatory agents in an acute inflammation mouse ear model, against the commercial glucocorticoid dexamethasone. The final compounds were all regioselectively obtained with an E configuration at the oxime double bond. The title compounds reduced ear-induced inflammation and edema. The most active oximes repressed the expression of proinflammatory genes TNF-α, COX-2, and IL-6; including macrophage migration inhibitory factor. Overall, our data suggest that 22-oxocholestane oximes exert a strong in vivo anti-inflammatory activity.
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