Synthesis of 3-(1,2,3-triazol-1-yl)- and 3-(1,2,3-triazol-4-yl)-substituted pyrazolo[3,4-d]pyrimidin-4-amines via click chemistry: potential inhibitors of the Plasmodium falciparum PfPK7 protein kinase

Klein, M., Dinér, P., Dorin-Semblat, D., Doerig, C. and Grøtli, M. (2009) Synthesis of 3-(1,2,3-triazol-1-yl)- and 3-(1,2,3-triazol-4-yl)-substituted pyrazolo[3,4-d]pyrimidin-4-amines via click chemistry: potential inhibitors of the Plasmodium falciparum PfPK7 protein kinase. Organic and Biomolecular Chemistry, 17, pp. 3421-3429. (doi: 10.1039/B906482F)

Abstract

Efficient routes to 3-(1,2,3-triazol-1-yl)- and 3-(1,2,3-triazol-4-yl)pyrazolo[3,4-d]pyrimidin-4-amines using a one-pot two-step reaction are presented. The two routes give easy access to two different isomers of 1,4-disubstituted triazoles and the target compounds are obtained from a variety of readily available aromatic and aliphatic halides without isolation of potentially unstable organic azide intermediates. Two compounds show activity towards the PfPK7 kinase (IC₅₀ 10–20 µM) of P. falciparum, the organism responsible for the most virulent form of malaria, and can be regarded as hits useful for further development into lead compounds.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Doerig, Dr Christian
• Authors: Klein, M., Dinér, P., Dorin-Semblat, D., Doerig, C., and Grøtli, M.
• College/School: College of Medical Veterinary and Life Sciences > School of Infection & Immunity
• Journal Name: Organic and Biomolecular Chemistry
• Journal Abbr.: Org. Biomol. Chem.
• ISSN: 1477-0520
• ISSN (Online): 1477-0539
• Published Online: 09 July 2009