Synthesis and Liver Microsomal Metabolic Stability Studies of a Fluorine‐Substituted δ‐Tocotrienol Derivative | Zendy

Liu Xingui | Zendy; Poddar Saikat | Zendy; Song Lin | Zendy; Hendrickson Howard | Zendy; Zhang Xuan | Zendy; Yuan Yaxia | Zendy; Zhou Daohong | Zendy; Zheng Guangrong | Zendy

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Synthesis and Liver Microsomal Metabolic Stability Studies of a Fluorine‐Substituted δ‐Tocotrienol Derivative

Author(s) -

Liu Xingui,

Poddar Saikat,

Song Lin,

Hendrickson Howard,

Zhang Xuan,

Yuan Yaxia,

Zhou Daohong,

Zheng Guangrong

Publication year - 2020

Publication title -

chemmedchem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.817

H-Index - 100

eISSN - 1860-7187

pISSN - 1860-7179

DOI - 10.1002/cmdc.201900676

Subject(s) - derivative (finance) , allylic rearrangement , microsome , chemistry , hydrolysis , tocotrienol , double bond , metabolic stability , stereochemistry , in vitro , organic chemistry , biochemistry , antioxidant , tocopherol , catalysis , vitamin e , financial economics , economics

A fluoro‐substituted δ‐tocotrienol derivative, DT3‐F2, was synthesized. This compound was designed to stabilize the metabolically labile terminal methyl groups of δ‐tocotrienol by replacing one C−H bond on each of the two methyl groups with a C−F bond. However, in vitro metabolic stability studies using mouse liver microsomes revealed an unexpected rapid enzymatic C−F bond hydrolysis of DT3‐F2. To the best of our knowledge, this is the first report of an unusual metabolic hydrolysis of allylic C−F bonds.

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