Synthesis of Deuterated Cycrimine Based on Multiple Deuteration of Cycloalkane Carboxylic Acid
Year: 2026
Type: article
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.
Language: English
Subfield: Pharmaceutical Science
Domain: Life Sciences
Open Access status: diamond
OpenAlex ID: W7215046682