〔Prolyl-U-14C〕 Alaceprilおよび関連化合物の合成

景本 昭; 中尾 全志; 根来 利行; 関根 豊; 橋本 昌久

doi:10.3769/radioisotopes.34.8_408

Syntheses of [Prolyl-U-¹⁴C] Alacepril and Its Related Compounds

Akira KAGEMOTO, Masashi NAKAO, Toshiyuki NEGORO, Yutaka SEKINE, Masahisa HASHIMOTO

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Keywords: anti-hypertensive agent, [prolyl-U-¹⁴C] alacepril, [prolyl-U-¹⁴C] DU-1227, [prolyl-U-¹⁴C] captopril, [prolyl-U-¹⁴C] captopril-cysteine, synthesis

JOURNAL FREE ACCESS

1985 Volume 34 Issue 8 Pages 408-413

DOI https://doi.org/10.3769/radioisotopes.34.8_408

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Abstract

In order to study the metabolic fate of alacepril, an anti-hypertensive agent, the ¹⁴C-labeled compound of alacepril and its related compounds were synthesized.
[Prolyl-U-¹⁴C] alacepril was synthesized in over-all yield of 32.7-38. 0% by the mixed anhydride condensation of L phenylalanine with [prolyl-U-¹⁴C] DU-1163, which had been prepared from L- [U-¹⁴C] proline and N (S 3-acetylthio-2-methylpropanoyloxy) succinimide. [Prolyl-U-¹⁴C] captopril and [prolyl-U-¹⁴C] DU-1227 were prepared in high yields by hydrolysis of [prolyl-U-¹⁴C] DU-1163 and [prolyl-U-¹⁴C] alacepril, respectively. [Prolyl-U-¹⁴C] captorilcysteine was synthesized by condensation of [prolyl-U-¹⁴C] captopril with cystine S-monoxide in 55.0% yield.

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