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

8 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)5666-5673
Number of pages8
JournalTetrahedron
Volume70
Issue number35
DOIs
StatePublished - Sep 2 2014
Externally publishedYes

Fingerprint

Bearings (structural)
Structural optimization
Palladium
Inhibitory Concentration 50
Catalytic Domain
Crystal structure
X-Rays
X rays

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides : Facile synthesis of PARP14 inhibitors. / Wang, Pingyuan; Li, Jian; Jiang, Xue; Liu, Zhiqing; Ye, Na; Xu, Youjun; Yang, Guangfu; Xu, Yechun; Zhang, Ao.

In: Tetrahedron, Vol. 70, No. 35, 02.09.2014, p. 5666-5673.

Research output: Contribution to journal › Article

Wang, P, Li, J, Jiang, X, Liu, Z, Ye, N, Xu, Y, Yang, G, Xu, Y & Zhang, A 2014, 'Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: Facile synthesis of PARP14 inhibitors', Tetrahedron, vol. 70, no. 35, pp. 5666-5673. https://doi.org/10.1016/j.tet.2014.06.064
Wang P, Li J, Jiang X, Liu Z, Ye N, Xu Y et al. Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: Facile synthesis of PARP14 inhibitors. Tetrahedron. 2014 Sep 2;70(35):5666-5673. https://doi.org/10.1016/j.tet.2014.06.064
Wang, Pingyuan ; Li, Jian ; Jiang, Xue ; Liu, Zhiqing ; Ye, Na ; Xu, Youjun ; Yang, Guangfu ; Xu, Yechun ; Zhang, Ao. / Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides : Facile synthesis of PARP14 inhibitors. In: Tetrahedron. 2014 ; Vol. 70, No. 35. pp. 5666-5673.
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AU - Liu, Zhiqing

AU - Ye, Na

AU - Xu, Youjun

AU - Yang, Guangfu

AU - Xu, Yechun

AU - Zhang, Ao

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