Biopolym. Cell. 2020; 36(6):466-476.
http://dx.doi.org/10.7124/bc.000A44
Bioorganic Chemistry
The synthesis of 5-hetarylamino-3-aryl-1H-indazoles as inhibitors of protein kinase CK2
1Protopopov M. V., 1Vdovin V. S., 1Lukashov S. S., 1Ostrynska O. V., 1, 2Borysenko I. P., 1Borovykov O. V., 1Starosyla S. A., 3Bilokin Y. V., 1Kukharenko O. P., 1Bdzhola V. G., 1Yarmoluk S. M.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03143
  2. LLC “Scientific and service firm “Otava”
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03143
  3. OTAVA Ltd
    400 Applewood Crescent, Unit 100, Vaughan, Ontario, L4K 0C3 Canada

Abstract

Aim. Basing of our earlier finding of inhibitory activity of 5-(4-quinazolylamino)-3-arylindazoles against human protein kinase CK2, the synthesis of 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 hetarocyclic 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]pyrimidine derivatives with decreased lipophilicity was synthesized.
Keywords: synthesis, indazole, quinazoline, thieno[2,3-d]pyrimidine, pyrazolo[3,4-d]pyrimidine, protein kinase CK2 inhibitor
Full text: (PDF, in English)

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