Synthesis of a human urate transporter-1 inhibitor, an arginine vasopressin antagonist, and a 17β-hydroxysteroid dehydrogenase type-3 inhibitor, using ring-expansion of cyclic ketoximes with DIBALH

Hidetsura Cho, Yusuke Iwama, Kentaro Okano, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Synthesis of three clinical candidates for medicines, a human urate transporter-1 inhibitor, an arginine vasopressin antagonist, and a 17β-hydroxysteroid dehydrogenase type-3 inhibitor, is described. These compounds were synthesized via construction of their 3,4-dihydro-2H-benzo[b][1, 4]oxazine, dibenzodiazepine, and dibenzazocine skeletons, respectively, using the reductive ring-expansion reaction of the corresponding bicyclic or tricyclic oximes with diisobutylaluminum hydride.

Original languageEnglish
Pages (from-to)354-363
Number of pages10
JournalChemical and Pharmaceutical Bulletin
Volume62
Issue number4
DOIs
Publication statusPublished - 2014 Apr

Keywords

  • 17β-hydroxysteroid dehydrogenase type-3 (17β-HSD3) inhibitor
  • Arginine vasopressin (AVP) antagonist
  • Cyclic oxime
  • Diisobutylaluminum hydride
  • Ring-expansion rearrangement
  • Urate transporter-1 (URAT-1) inhibitor

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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