使用手性衍生化试剂1-氟茚-1-羧酸测定萘丁美酮代谢物4-(6-甲氧基-2-萘基)丁-2-醇的绝对构型

Determination of the Absolute Configuration of the Nabumetone Metabolite 4-(6-Methoxy-2-naphthyl)butan-2-ol Using the Chiral Derivatizing Agent, 1-Fluoroindan-1-carboxylic Acid.

作者信息

Kamei Tomoyo, Kimura Yuta, Koyanagi Jyunichi, Matsumoto Kaori, Hasegawa Tetsuya, Akimoto Masayuki, Takahashi Tamiko

机构信息

Faculty of Pharmaceutical Sciences, Josai International University.

出版信息

Chem Pharm Bull (Tokyo). 2019;67(1):75-78. doi: 10.1248/cpb.c18-00694.

DOI:10.1248/cpb.c18-00694

PMID:30606953

Abstract

The absolute configuration of (+)-4-(6-methoxy-2-naphthyl)butan-2-ol ((+)-MNBO), a nabumetone metabolite, was determined using 1-fluoroindan-1-carboxylic acid (FICA). Both enantiomers of the FICA methyl esters were derivatized to diastereomeric esters of (+)-MNBO by an ester exchange reaction. The results of H- and F-NMR spectroscopy of the diastereomeric FICA esters of (+)-MNBO confirmed the absolute configuration of (+)-MNBO was (S).

摘要

萘丁美酮代谢物（+）-4-（6-甲氧基-2-萘基）丁-2-醇（（+）-MNBO）的绝对构型通过1-氟茚-1-羧酸（FICA）确定。FICA甲酯的两种对映体通过酯交换反应衍生化为（+）-MNBO的非对映体酯。（+）-MNBO的非对映体FICA酯的氢谱和氟谱结果证实（+）-MNBO的绝对构型为（S）型。