Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues

[Image: see text] Two novel 23-fluorinated 25-hydroxyvitamin D(3) analogues were synthesized using Inhoffen–Lythgoe diol as a precursor of the CD-ring, efficiently. Introduction of the C23 fluoro group was achieved by the deoxy-fluorination reaction using N,N-diethylaminosulfur trifluoride or 2-pyri...

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Detalles Bibliográficos
Autores principales: Kawagoe, Fumihiro, Yasuda, Kaori, Mototani, Sayuri, Sugiyama, Toru, Uesugi, Motonari, Sakaki, Toshiyuki, Kittaka, Atsushi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648426/
https://www.ncbi.nlm.nih.gov/pubmed/31460236
http://dx.doi.org/10.1021/acsomega.9b01500
Descripción
Sumario:[Image: see text] Two novel 23-fluorinated 25-hydroxyvitamin D(3) analogues were synthesized using Inhoffen–Lythgoe diol as a precursor of the CD-ring, efficiently. Introduction of the C23 fluoro group was achieved by the deoxy-fluorination reaction using N,N-diethylaminosulfur trifluoride or 2-pyridinesulfonyl fluoride (PyFluor). Kinetic studies on the CYP24A1-dependent metabolism of these two analogues revealed that (23S)-23-fluoro-25-hydroxyvitamin D(3) was more resistant to CYP24A1-dependent metabolism than its 23R isomer.

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