Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: Facile synthesis of PARP14 inhibitors

Pingyuan Wang; Jian Li; Xue Jiang; Zhiqing Liu; Na Ye; Youjun Xu; Guangfu Yang; Yechun Xu; Ao Zhang

doi:10.1016/j.tet.2014.06.064

Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: Facile synthesis of PARP14 inhibitors

Pingyuan Wang, Jian Li, Xue Jiang, Zhiqing Liu, Na Ye, Youjun Xu, Guangfu Yang, Yechun Xu, Ao Zhang

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

13 Scopus citations

Abstract

We have developed a palladium-catalyzed N-arylation of the biologically interesting, but synthetically rather challenging 2-arylaminobenzothiazoles bearing multiple functionalities. This protocol was successfully used to readily synthesize our initial PARP14 inhibitor followed by a limited structural optimization. A more potent PARP14 inhibitor with an IC₅₀ value of 1.69 μM was identified, and the interaction was ascertained by the X-ray co-crystal structure of the catalytic domain of PARP14 in complex with compound 8.

Original language	English (US)
Pages (from-to)	5666-5673
Number of pages	8
Journal	Tetrahedron
Volume	70
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2014.06.064
State	Published - Sep 2 2014
Externally published	Yes

Keywords

2-Arylaminobenzothiazoles
C-N coupling
N-arylation
PARP14
Pd(dba)

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.06.064

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title = "Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: Facile synthesis of PARP14 inhibitors",

abstract = "We have developed a palladium-catalyzed N-arylation of the biologically interesting, but synthetically rather challenging 2-arylaminobenzothiazoles bearing multiple functionalities. This protocol was successfully used to readily synthesize our initial PARP14 inhibitor followed by a limited structural optimization. A more potent PARP14 inhibitor with an IC50 value of 1.69 μM was identified, and the interaction was ascertained by the X-ray co-crystal structure of the catalytic domain of PARP14 in complex with compound 8.",

keywords = "2-Arylaminobenzothiazoles, C-N coupling, N-arylation, PARP14, Pd(dba)",

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year = "2014",

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T1 - Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides

T2 - Facile synthesis of PARP14 inhibitors

AU - Wang, Pingyuan

AU - Li, Jian

AU - Jiang, Xue

AU - Liu, Zhiqing

AU - Ye, Na

AU - Xu, Youjun

AU - Yang, Guangfu

AU - Xu, Yechun

AU - Zhang, Ao

PY - 2014/9/2

Y1 - 2014/9/2

N2 - We have developed a palladium-catalyzed N-arylation of the biologically interesting, but synthetically rather challenging 2-arylaminobenzothiazoles bearing multiple functionalities. This protocol was successfully used to readily synthesize our initial PARP14 inhibitor followed by a limited structural optimization. A more potent PARP14 inhibitor with an IC50 value of 1.69 μM was identified, and the interaction was ascertained by the X-ray co-crystal structure of the catalytic domain of PARP14 in complex with compound 8.

AB - We have developed a palladium-catalyzed N-arylation of the biologically interesting, but synthetically rather challenging 2-arylaminobenzothiazoles bearing multiple functionalities. This protocol was successfully used to readily synthesize our initial PARP14 inhibitor followed by a limited structural optimization. A more potent PARP14 inhibitor with an IC50 value of 1.69 μM was identified, and the interaction was ascertained by the X-ray co-crystal structure of the catalytic domain of PARP14 in complex with compound 8.

KW - 2-Arylaminobenzothiazoles

KW - C-N coupling

KW - N-arylation

KW - PARP14

KW - Pd(dba)

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DO - 10.1016/j.tet.2014.06.064

M3 - Article

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SN - 0040-4020

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SP - 5666

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JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: Facile synthesis of PARP14 inhibitors

Abstract

Keywords

ASJC Scopus subject areas

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