Synthesis of Deuterated Cycrimine Based on Multiple Deuteration of Cycloalkane Carboxylic Acid
Abstract
In recent years, deuterated pharmaceuticals (heavy drugs) have attracted significant attention as novel drug discovery modalities. While the stronger C-D bonds, as compared to C-H bonds, result in improved metabolic stability, the introduction of multiple deuterium atoms alters the physicochemical properties. Among the various methods developed for the synthesis of deuterated compounds, H/D exchange reactions are regarded as the most straightforward and useful. Herein, we developed a direct method for the multiple deuteration (H/D exchange reactions) of sodium cycloalkanecarboxylates bearing cyclopentane and cyclobutane rings using deuterium oxide, the most inexpensive deuterium source, in the presence of a Pt/C catalyst. Furthermore, deuterated cycrimine was synthesized from the deuterated sodium cyclopentanecarboxylate, and the effect of deuteration on lipophilicity was evaluated by a parallel artificial membrane permeability assay. Although no significant difference in lipophilicity was observed between the deuterated and hydrogenated forms, this study provides a useful method for the synthesis of deuterated compounds and a new synthetic approach to deuterated pharmaceuticals.
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BibTeX
@article{suganuma2026synthesis,
title = {{Synthesis of Deuterated Cycrimine Based on Multiple Deuteration of Cycloalkane Carboxylic Acid}},
author = {Yuto Suganuma and Hiromasa Uchiyama and Yuichi Tozuka and Akira Yada and Yoshinari Sawama},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2026},
month = oct,
doi = {10.1248/cpb.c26-00415},
url = {https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00415/_article},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - Synthesis of Deuterated Cycrimine Based on Multiple Deuteration of Cycloalkane Carboxylic Acid
AU - Yuto Suganuma
AU - Hiromasa Uchiyama
AU - Yuichi Tozuka
AU - Akira Yada
AU - Yoshinari Sawama
PY - 2026
DA - 2026/10/02
JO - Chemical and Pharmaceutical Bulletin
DO - 10.1248/cpb.c26-00415
UR - https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00415/_article
AB - In recent years, deuterated pharmaceuticals (heavy drugs) have attracted significant attention as novel drug discovery modalities. While the stronger C-D bonds, as compared to C-H bonds, result in improved metabolic stability, the introduction of multiple deuterium atoms alters the physicochemical properties. Among the various methods developed for the synthesis of deuterated compounds, H/D exchange reactions are regarded as the most straightforward and useful. Herein, we developed a direct method for the multiple deuteration (H/D exchange reactions) of sodium cycloalkanecarboxylates bearing cyclopentane and cyclobutane rings using deuterium oxide, the most inexpensive deuterium source, in the presence of a Pt/C catalyst. Furthermore, deuterated cycrimine was synthesized from the deuterated sodium cyclopentanecarboxylate, and the effect of deuteration on lipophilicity was evaluated by a parallel artificial membrane permeability assay. Although no significant difference in lipophilicity was observed between the deuterated and hydrogenated forms, this study provides a useful method for the synthesis of deuterated compounds and a new synthetic approach to deuterated pharmaceuticals.
SN - 1347-5223
SN - 0009-2363
ER -