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 | |
| State | Published - Sep 2 2014 |
| Externally published | Yes |
Keywords
- 2-Arylaminobenzothiazoles
- C-N coupling
- N-arylation
- PARP14
- Pd(dba)
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Fingerprint Dive into the research topics of 'Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: Facile synthesis of PARP14 inhibitors'. Together they form a unique fingerprint.
Cite this
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, 70(35), 5666-5673. https://doi.org/10.1016/j.tet.2014.06.064