The synthesis of 5-hetarylamino-3-aryl-1H-indazoles as inhibitors of protein kinase CK2

Abstract

Aim. Basing on our earlier finding of inhibitory activity of 5-(4-quinazolylamino)-3-arylinda-zoles against human protein kinase CK2, the synthesis of new nitrogen containing heterocyclic derivatives was performed in order to find novel inhibitors of this kinase. Methods. Organic synthesis, NMR spectroscopy. Results. A series of 4-chloroquinazolines, 4-chloroquinolines, 4-chloropyrazolo[3,4-d]pyrimidines and 4-chlorothieno[2,3-d]pyrimidine was synthesized. Reaction of these intermediates with 5-amino-3-(3,4-dichlorophenyl)-indazole gave us a series of 14 novel heterоcyclic derivatives of 5-amino-3-arylindazole. Conclusions. Besides new quinazoline derivatives – the quinoline and thieno[2,3-d]pyrimidine derivatives of similar structure but different polarity were obtained. Also a series of 1-methylpyrazolo[3,4-d]py-rimidine derivatives with decreased lipophilicity was synthesized.