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 journalArticle

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

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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