Click-based synthesis of triazolobithiazole Δf508-CFTR correctors for cystic fibrosis

Michael B. Donald; Kevin X. Rodriguez; Hannah Shay; Puay Wah Phuan; A. S. Verkman; Mark J. Kurth

doi:10.1016/j.bmc.2012.06.046

Click-based synthesis of triazolobithiazole Δf508-CFTR correctors for cystic fibrosis

Michael B. Donald, Kevin X. Rodriguez, Hannah Shay, Puay Wah Phuan, A. S. Verkman, Mark J. Kurth

Chemistry

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

13 Scopus citations

Abstract

Copper catalyzed azide-alkyne cycloaddition (CuAAC) chemistry is reported for the construction of previously unknown 5-(1H-1,2,3-triazol-1-yl)-4,5′- bithiazoles from 2-bromo-1-(thiazol-5-yl)ethanones. These novel triazolobithiazoles are shown to have cystic fibrosis (CF) corrector activity and, compared to the benchmark bithiazole CF corrector corr-4a, improved log P values (4.5 vs 5.96).

Original language	English (US)
Pages (from-to)	5247-5253
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	20
Issue number	17
DOIs	https://doi.org/10.1016/j.bmc.2012.06.046
State	Published - Sep 1 2012

Keywords

CF corrector
CuAAC
Cystic fibrosis
Triazolobithiazole

ASJC Scopus subject areas

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

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10.1016/j.bmc.2012.06.046

Cite this

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title = "Click-based synthesis of triazolobithiazole Δf508-CFTR correctors for cystic fibrosis",

abstract = "Copper catalyzed azide-alkyne cycloaddition (CuAAC) chemistry is reported for the construction of previously unknown 5-(1H-1,2,3-triazol-1-yl)-4,5′- bithiazoles from 2-bromo-1-(thiazol-5-yl)ethanones. These novel triazolobithiazoles are shown to have cystic fibrosis (CF) corrector activity and, compared to the benchmark bithiazole CF corrector corr-4a, improved log P values (4.5 vs 5.96).",

keywords = "CF corrector, CuAAC, Cystic fibrosis, Triazolobithiazole",

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T1 - Click-based synthesis of triazolobithiazole Δf508-CFTR correctors for cystic fibrosis

AU - Donald, Michael B.

AU - Rodriguez, Kevin X.

AU - Shay, Hannah

AU - Phuan, Puay Wah

AU - Verkman, A. S.

AU - Kurth, Mark J.

PY - 2012/9/1

Y1 - 2012/9/1

N2 - Copper catalyzed azide-alkyne cycloaddition (CuAAC) chemistry is reported for the construction of previously unknown 5-(1H-1,2,3-triazol-1-yl)-4,5′- bithiazoles from 2-bromo-1-(thiazol-5-yl)ethanones. These novel triazolobithiazoles are shown to have cystic fibrosis (CF) corrector activity and, compared to the benchmark bithiazole CF corrector corr-4a, improved log P values (4.5 vs 5.96).

AB - Copper catalyzed azide-alkyne cycloaddition (CuAAC) chemistry is reported for the construction of previously unknown 5-(1H-1,2,3-triazol-1-yl)-4,5′- bithiazoles from 2-bromo-1-(thiazol-5-yl)ethanones. These novel triazolobithiazoles are shown to have cystic fibrosis (CF) corrector activity and, compared to the benchmark bithiazole CF corrector corr-4a, improved log P values (4.5 vs 5.96).

KW - CF corrector

KW - CuAAC

KW - Cystic fibrosis

KW - Triazolobithiazole

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JO - Bioorganic and Medicinal Chemistry

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Click-based synthesis of triazolobithiazole Δf508-CFTR correctors for cystic fibrosis

Abstract

Keywords

ASJC Scopus subject areas

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