フェニルプロピオン酸誘導体の重水素標識化合物の合成

森 幸雄; 柴田 正芳; 酒井 淑行; 横家 房志; 豊吉 一美; 馬場 茂雄

doi:10.3769/radioisotopes.32.11_533

Syntheses of Deuterated Phenylpropionic Acid Derivatives

Yukio MORI, Masayoshi SHIBATA, Yoshiyuki SAKAI, Fusayuki YOKOYA, Kazumi TOYOSHI, Shigeo BABA

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Keywords: 2- (4- (2-thienylcarbonyl) phenyl) propionic acid metabolism, mass fragmentography, 2- (4- (2-thienylhydroxymethyl) phenyl) propionic acid, 2- (4-carboxyphenyl) propionic acid, 2- (4- (5-hydroxy-2-thienylcarbonyl) phenyl) propionic acid, multiple-deuterium labeling, mass spectrometry

JOURNAL FREE ACCESS

1983 Volume 32 Issue 11 Pages 533-538

DOI https://doi.org/10.3769/radioisotopes.32.11_533

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Abstract

2- (4- (2-Thienylhydroxymethyl) phenyl) propionic acid (I), 2- (4-carboxyphenyl) propionic acid (II), 2- (4- (5-hydroxy-2-thienylcarbonyl) phenyl) propionic acid (III) were labeled with multiple-deuterium for the purpose of using as internal standards in studies on the metabolism of 2- (4- (2-thienylcarbonyl) phenyl) propionic acid (suprofen, IV), anti-inflammatory agent, in man and animals by the mass fragmentography. I-d₄ was obtained in a 93%yield from IV-d₄ by reduction with sodium borohydride, and its deuterium content was 99 atom%. On the other hand, II-d₄ (99 atom%D) was obtained by four-step synthesis from 2- ( (4-bromophenyl-d₄) 1, 1-ethyleneglycol) propane (V) in a 43% yield and III-d₄ (98.4 atom% D) by five-step synthesis from V in a 12% yield.

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