{
  "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.",
  "abstract_shown": true,
  "affiliations": [],
  "article_type": null,
  "arxiv": null,
  "author_total": 5,
  "authors": [
    {
      "name": "Yuto Suganuma"
    },
    {
      "name": "Hiromasa Uchiyama"
    },
    {
      "name": "Yuichi Tozuka"
    },
    {
      "name": "Akira Yada"
    },
    {
      "name": "Yoshinari Sawama"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/3qbgr3vvzxx5k.bib",
  "cited_by": 0,
  "doi": "10.1248/cpb.c26-00415",
  "fulltext_url": "https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00415/_article",
  "id": "3qbgr3vvzxx5k",
  "issns": [
    "1347-5223",
    "0009-2363"
  ],
  "landing_url": "https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00415/_article",
  "language": null,
  "licence": "CC-BY-NC",
  "licence_label": "CC BY-NC",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by-nc/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "jstage-journal",
      "chemistry/medicinal"
    ],
    [
      "openalex",
      "3003|Chemical Reactions and Isotopes"
    ]
  ],
  "openalex": "W7215046682",
  "pdf_url": "https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00415/_pdf",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-02",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/3qbgr3vvzxx5k.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:34Z",
      "native_id": "10.1248/cpb.c26-00415",
      "source": "jstage",
      "url": "https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00415/_article"
    }
  ],
  "subjects": [
    {
      "field": "medicine",
      "origin": "openalex:3003|Chemical Reactions and Isotopes",
      "subfield": "pharmacology-toxicology"
    }
  ],
  "title": "Synthesis of Deuterated Cycrimine Based on Multiple Deuteration of Cycloalkane Carboxylic Acid",
  "title_text": "Synthesis of Deuterated Cycrimine Based on Multiple Deuteration of Cycloalkane Carboxylic Acid",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:17:34Z",
  "url": "https://research.draconitic.com/paper/3qbgr3vvzxx5k",
  "venue": "Chemical and Pharmaceutical Bulletin",
  "versions": []
}