O- and N-glycosides of pyrazolo[3,4-c]isoquinoline. Synthesis and structural investigation by NMR

Authors

DOI:

https://doi.org/10.15407/dopovidi2026.01.040

Keywords:

pyrazolo[3,4-c]isoquinolines, glycosylation, correlation spectroscopy, N,O-glucosides, oxazoline.

Abstract

The synthetic potential of polyfunctional derivatives of the condensed system of pyrazolo[3,4-c] isoquinoline has been investigated. For the first time, a series of derivatives with a glucosamine fragment has been obtained and their spectral properties have been described.

Downloads

Download data is not yet available.

References

Bogza, S. L., Kobrakov, K. I., Malienko, A. A., Sujkov, S. Yu., Perepichka, I. F., Bryce, M. R., Bogdan, N. M. & Dulenko, V. I. (2001). Convenient one pot synthesis of 5-unsubstituted pyrazolo[3,4-c]isoquinolines. J. Heterocyclic Chem., 38, No. 2, pp. 523-525. https://doi.org/10.1002/jhet.5570380238

Bogza, S. L., Kobrakov, K. I., Malienko, A. A., Perepichka, I. F., Sujkov, S. Yu., Bryce, M. R., Lyubchik, S. B., Batsanovc, A. S. & Bogdan, N. M. (2005). A versatile synthesis of pyrazolo[3,4-c]isoquinoline derivatives by reaction of 4-aryl-5-aminopyrazoles with aryl/heteroaryl aldehydes: the effect of the heterocycle on the reaction pathways. Org. Biomol. Chem., 3, No. 5, pp. 932-940. https://doi.org/10.1039/B417002D

Li R., Xue L., Zhu T., Jiang Q., Cui X., Yan Z., McGee D., Wang J., Gantla V. R., Pickens J. C., McGrath D., Chucholowski A., Morris S. W. & Webb T. R. (2006). Design and synthesis of 5-aryl-pyridone-carboxamides as inhibitors of anaplastic lymphoma kinase. J. Med. Chem., No. 49, No. 3, pp. 1006-1015. https://doi. org/10.1021/jm050824x

Lu, B., Cao, H., Cao, J., Huang, S., Hu, Q., Liu, D., Shen, R., Shen, X., Tao, W., Wan, H., Wang, D., Yan, Y., Yang, L., Zhang, J., Zhang, L., Zhang, L. & Zhang, M. (2016). Discovery of EBI-907: A highly potent and orally active B-RafV600E inhibitor for the treatment of melanoma and associated cancers. Bioorg. Med.

Chem. Lett., 26, No. 3, pp. 819-823. https://doi.org/10.1016/j.bmcl.2015.12.086

Milkiewicz, K. L. & Ott, G. R. (2010). Inhibitors of anaplastic lymphoma kinase: a patent review. Expert Opin. Ther. Pat., 20, No. 12, pp. 1653-1681. https://doi.org/10.1517/13543776.2010.527332

Kondratov, R. V., Komarov, P. G., Becker, Y., Ewenson, A. & Gudkov, A. V. (2001). Small molecules that dramatically alter multidrug resistance phenotype by modulating the substrate specificity of P-glycoprotein. PNAS, 98, No. 24, pp. 14078-14083. https://doi.org/10.1073/pnas.241314798

Nikoljukin, Yu. A., Zubrickij, M. Yu. & Dulenko, V. I. (1993). Synthesis of pyrrolo[3,4-c]isoquinolinediones and pyrrolo[3,4-c]-β-carbolinedione. Zhurn. org. himii, 29, No. 7, pp. 1480-1484 (in Russian).

Zinchenko, S. Yu., Efimenko, R. A., Suikov, S. Yu., Kobrakov, K. I. & Bogza, S. L. (2009). Acid cyclization of amino-substituted heterocycles. Synthesis of 1,3-dioxo-pyrrolo[3,4-c]- and thieno[3,4-c]isoquino-lines and cinnolines. Chem. Heterocycl. Comp., 45, pp. 365-369. https://doi.org/10.1007/s10593-009-0262-2

Zhong, H., Zou, H., Semenov, M. V., Moshinsky D., He X., Huang H., Li S., Quan J., Yanga Z. & Lin S. (2009). Characterization and development of novel small-molecules inhibiting GSK3 and activating Wnt signaling. Mol. BioSyst., 5, No. 11, pp. 1356-1360. https://doi.org/10.1039/B905752H

Teller, S., Eluwa, S., Koller, M., Uecker, A., Beckers, T., Baasner, S., Böhmer, F.-D. & Mahboobi, S. (2000). Pyrrolo[3,4-c]-β-carboline-diones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase. Eur. J. Med. Chem., 35, No. 4, pp0. 413-427. https://doi.org/10.1016/S0223-5234(00)00140-9

Wong, N. W. Y. & Forgione, P. (2012). A one-pot double C—H activation palladium catalyzed route to a unique class of highly functionalized thienoisoquinolines. Org. Lett., 14, No. 11, pp. 2738-2741. https://doi. org/10.1021/ol3009655

Kur’yanov, V. O., Chupakhina, T. A., Zemlyakov, A. E., Kotlyar, S. A., Kamalov, G. L. & Chirva, V. Ya. (2001). Synthesis of N-acetylglucosamine aryl β-glycosides catalyzed by crown compounds. Rus. J. Bioorg. Chem., 27, pp. 385-389. https://doi.org/10.1023/A:1012988719296

Kur’yanov, V. O., Priskoka, U. S., Chupakhina, T. A. & Chirva, V. Ya. (2005). A phase-transfer glucosamination of phenols catalyzed by polyethylene glycol. Rus. J. Bioorg. Chem., 31, pp. 301-304. https://doi.org/10.1007/ s11171-005-0042-4

Zinner, H. & Peseke, C. (1965). Benzazole, XIX. Glykoside des Benzthiazolthions. Chem. Ber., 98, No. 11, pp. 3508-3514. https://doi.org/10.1002/cber.19650981110

Nikolyukin, Yu. A., Dulenko, L. V. & Dulenko, V. I. (1990). Synthesis of azolo[5,4-c]isoquinolines. Chem. Heterocycl. Compd., 26, pp. 914-917. https://doi.org/10.1007/BF00480870

Downloads

Published

27.02.2026

How to Cite

Bohdan, N., Bohza, S., Bousta, D., Grafov, A., Holembiovska, O., Khairulin, A., & Suikov, S. (2026). O- and N-glycosides of pyrazolo[3,4-c]isoquinoline. Synthesis and structural investigation by NMR. Reports of the National Academy of Sciences of Ukraine, (1), 40–49. https://doi.org/10.15407/dopovidi2026.01.040