A versatile strategy for the synthesis of crown ether-bearing heterocycles: Discovery of calcium-selective fluoroionophore

Yuko Aoki, Naoki Umezawa, Yuko Asano, Keiichiro Hatano, Yuki Yano, Nobuki Kato, Tsunehiko Higuchi

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

Heterocycles have been modified in various ways in the search for new functions, but few examples are known of crown ethers incorporating heterocycles in macro-ring systems. Here we report a simple and versatile synthesis of crown ether-bearing heterocycles. An acylurea moiety in the heterocycles is efficiently transformed to 'crown ether' of various ring sizes. The products included a Ca2+-selective fluoroionophore. Our simple methodology is expected to provide many novel functional heterocyclic compounds, including fluoroionophores and candidate pharmaceuticals.

Original languageEnglish
Pages (from-to)7108-7115
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume15
Issue number22
DOIs
Publication statusPublished - 2007 Nov 15

Keywords

  • Acylurea
  • Calcium
  • Cesium effect
  • Coordination
  • Crown ether
  • Crystal structure
  • Fluorescence
  • Fluoroionophore
  • Heterocycle
  • Lumazine
  • Lumichrome
  • Magnesium
  • Metal sensor
  • One-step synthesis
  • Phenobarbital
  • Phenytoin
  • Selectivity
  • Uracil

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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