Base Catalyzed Microwave Assisted Synthesis, Characterization of 6-Bromo-Pyrazolo-[1,5-a]-Pyrimidine-3-Ethyl-Carboxylate &amp; Its Biological Evaluation as CDKs Inhibitor

Ganesh N. Yallapa1; D. Nagaraja2; U. Ch

doi:10.14233/ajchem.2018.21357

Issue

Vol. 30 No. 8 (2018): Vol 30 Issue 8

Issue Published : June 30, 2018

This work is licensed under a Creative Commons Attribution 4.0 International License.

Base Catalyzed Microwave Assisted Synthesis, Characterization of 6-Bromo-Pyrazolo-[1,5-a]-Pyrimidine-3-Ethyl-Carboxylate & Its Biological Evaluation as CDKs Inhibitor

https://doi.org/10.14233/ajchem.2018.21357%20

Ganesh N. Yallapa1

1Department of Chemistry, VTU-RRC, Visvesvarayya Technological University, Belagavi-590 018, India 2Department of PG Studies in Chemistry, Govt. Science College, Chitradurga-577 501, India 3Department of Chemistry, University BDT College of Engineering, Visvesvarayya Technological University, Davangere-577 002, India *Corresponding author: E-mail: gindi.ny1988@gmail.com

D. Nagaraja2

U. Ch

Asian Journal of Chemistry, Vol. 30 No. 8 (2018): Vol 30 Issue 8
Article Published : June 30, 2018

Abstract

In this work, 5-amino-1H-pyrazole-4-ethyl-carboxylate is synthesized by treating ethyl cyanoacetate and hydrazine hydrate in presence of different nanometal-oxide catalysts under solvent free microwave conditions. The yield quantity of the synthesized compounds varies for specific catalysts. 6-Bromopyrazolo-[1,5-a]-pyrimidine-3-ethyl-carboxylate was synthesized by reaction of 5-amino-1H-pyrazole-4-ethyl-carboxylate with 2-bromo-malonaldehyde using different bases. The rate of reactions were found to be influenced on the strength of bases. The synthesized compounds were confirmed by FT-IR, ¹H NMR and LC-MS spectra. Then the compound 6-bromo-pyrazolo-[1,5-a]-pyrimidine-3-ethyl-carboxylate was tested for in vitro biological activity as CDKs inhibitor. It showed better IC₅₀ values for CDK4 and CDK6 than roscovitine. Thus, the synthesized compound is a selective inhibitor or acceptor for abnormal cancer cell line (CDKs).

Keywords

Pyrazolo-pyrimidines Nano metal-oxides Cyclin dependent kinase.

N. Yallapa1, G., Nagaraja2, D., & Ch, U. (2018). Base Catalyzed Microwave Assisted Synthesis, Characterization of 6-Bromo-Pyrazolo-[1,5-a]-Pyrimidine-3-Ethyl-Carboxylate & Its Biological Evaluation as CDKs Inhibitor. Asian Journal of Chemistry, 30(8), 1881–1884. https://doi.org/10.14233/ajchem.2018.21357

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References

D. Nagaraja and M.A. Pasha, Indian J. Chem., 40B, 1172 (2001).

G.N. Yallappa, D. Nagaraja and U. Chandrashekhar, Heterocycl. Lett., 8, 79 (2018).

A.M. Salaheldin, Z. Naturforsch. B, 64, 840 (2009); https://doi.org/10.1515/znb-2009-0712.

B.S. Holla, M.K. Shivananda, P.M. Akberali and M.S. Shenoy, Indian J. Chem., 39B, 440 (2000).

A.M. Salaheldin, A.M.F. Oliveira-Campos and L.M. Rodrigues, ARKIVOC, 180 (2008); https://doi.org/10.3998/ark.5550190.0009.e18.

R. Aggarwal, V. Kumar, R. Kumar and S.P. Singh, Beilstein J. Org. Chem., 7, 179 (2011); https://doi.org/10.3762/bjoc.7.25.

V. Polshettiwar and R.S. Varma, Tetrahedron, 66, 1091 (2010); https://doi.org/10.1016/j.tet.2009.11.015.

M. El Fal, Y. Ramli, A. Zerzouf, A. Talbaoui, Y. Bakri and E.M. Essassi, J. Chem., Article ID 982404 (2015); https://doi.org/10.1155/2015/982404.

S. Schenone, O. Bruno, M. Radi and M. Botta, Mini-Rev. Org. Chem., 6, 220 (2009); https://doi.org/10.2174/157019309788922739.s

S.R. Shejale, S.S. Awati, J.M. Gandhi, S.B. Satpute, S.S. Patil and M.S. Kondawar, Der Pharma Chem., 6, 75 (2014).

S.U. Tekale, S.S. Kauthale, K.M. Jadhav and R.P. Pawar, J. Chem., Article ID 840954 (2013); http://dx.doi.org/10.1155/2013/840954.

D.A. Heathcote, H. Patel, S.H.B. Kroll, P. Hazel, M. Periyasamy, M. Alikian, S.K. Kanneganti, A.S. Jogalekar, B. Scheiper, M. Barbazanges, A. Blum, J. Brackow, A. Siwicka, R.D.M. Pace, M.J. Fuchter, J.P. Snyder, D.C. Liotta, P.S. Freemont, E.O. Aboagye, R.C. Coombes, A.G.M. Barrett and S. Ali, J. Med. Chem., 53, 8508 (2010); https://doi.org/10.1021/jm100732t.

R. Jorda, K. Paruch and V. Krystof, Curr. Pharm. Des., 18, 2974 (2012); https://doi.org/10.2174/138161212800672804.

T. Gucký, R. Jorda, M. Zatloukal, V. Bazgier, K. Berka, E. Reznícková, T. Béres, M. Strnad and V. Krystof, J. Med. Chem., 56, 6234 (2013); https://doi.org/10.1021/jm4006884.