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

doi:10.1016/j.bmc.2007.07.035

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

SCI - Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	7108-7115
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	15
Issue number	22
DOIs	https://doi.org/10.1016/j.bmc.2007.07.035
Publication status	Published - 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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A versatile strategy for the synthesis of crown ether-bearing heterocycles : Discovery of calcium-selective fluoroionophore. / Aoki, Yuko; Umezawa, Naoki; Asano, Yuko; Hatano, Keiichiro; Yano, Yuki; Kato, Nobuki; Higuchi, Tsunehiko.

In: Bioorganic and Medicinal Chemistry, Vol. 15, No. 22, 15.11.2007, p. 7108-7115.

Research output: Contribution to journal › Article › peer-review

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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.",

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author = "Yuko Aoki and Naoki Umezawa and Yuko Asano and Keiichiro Hatano and Yuki Yano and Nobuki Kato and Tsunehiko Higuchi",

note = "Funding Information: This research was supported in part by a Grant-in-Aid for University and Society Collaboration (No. 12793009) from the Ministry of Education, Science, Sports and Culture, Japan.",

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AU - Yano, Yuki

AU - Kato, Nobuki

AU - Higuchi, Tsunehiko

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