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

Access to Document

10.1016/j.bmc.2012.06.046

Fingerprint Dive into the research topics of 'Click-based synthesis of triazolobithiazole Δf508-CFTR correctors for cystic fibrosis'. Together they form a unique fingerprint.

Cite this

@article{2d2fef0e603b4e41940758d999b44735,

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",

author = "Donald, {Michael B.} and Rodriguez, {Kevin X.} and Hannah Shay and Phuan, {Puay Wah} and Verkman, {A. S.} and Kurth, {Mark J.}",

year = "2012",

month = sep,

day = "1",

doi = "10.1016/j.bmc.2012.06.046",

language = "English (US)",

volume = "20",

pages = "5247--5253",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "17",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84864984030&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84864984030&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2012.06.046

DO - 10.1016/j.bmc.2012.06.046

M3 - Article

C2 - 22841006

AN - SCOPUS:84864984030

VL - 20

SP - 5247

EP - 5253

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 17

ER -