Issue

Vol. 36 No. 12 (2024): Vol 36 Issue 12, 2024

Copyright (c) 2024 Ganesh N. Yallappa, Laliteshwar Pratap Singh, Nerella Mounika, V.S. Cisma, Hemalatha Sattu, Uttam Prasad Panigrahy, V. Rajeshwar, Venugopal Muralidharan

Creative Commons License

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

Ionic Liquid Catalyzed Microwave Assisted Synthesis, Characterization and Anticancer Activity of Novel Pyrazolo[3,4-d]pyrimidine Derivatives

https://doi.org/10.14233/ajchem.2024.32811
Ganesh N. Yallappa
Department of Medicinal Chemistry Jain Institute of Technology (Affiliated to Visvesvarayya Technological University, Belagavi), Davangere-577005, India
https://orcid.org/0000-0002-7403-1884
Laliteshwar Pratap Singh
Department of Pharmaceutical Chemistry, Narayan Institute of Pharmacy, Gopal Narayan Singh University, Jamuhar, Sasaram (Rohtas)-821305, India
https://orcid.org/0000-0002-5594-6229
Nerella Mounika
Department of Pharmacology, Anurag University, Hyderabad-500088, India
V.S. Cisma
Karpagam College of Pharmacy, Othakalmandapam, Coimbatore-641032, India
Hemalatha Sattu
Department of Pharmaceutical Chemistry. S.N. Vanita Pharmacy Mahavidyalaya, Tarnaka, Secunderabad-500017, India
https://orcid.org/0000-0003-3721-6705
Uttam Prasad Panigrahy
Faculty of Pharmaceutical Science, Assam Downtown University, Panikhaiti, Guwahati-781026, India
https://orcid.org/0000-0002-8142-044X
V. Rajeshwar
Department of Pharmaceutics, Anurag University, Hyderabad-500088, India
https://orcid.org/0000-0002-4251-5550
Venugopal Muralidharan
Department of Pharmaceutical Chemistry, Vishnu Institute of Pharmaceutical Education and Research, Narsapur, Hyderabad-502313, India
https://orcid.org/0000-0002-2479-8374

Corresponding Author(s) : Venugopal Muralidharan

vmd1213@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 12 (2024): Vol 36 Issue 12, 2024

Abstract

A rapid and efficient method has been developed for the synthesis of pyrazolo[3,4-d]pyrimidines (5a-j) via microwave assisted method as well as conventional method using four components system in the presence of ionic liquid 2-methyl-imidazolium thiocyanate as a green catalyst. It was found that ionic liquid showed better reactivity than p-toluene-sulfonic acid (p-TSA) and L-proline. All the synthesized pyrazolo-pyrimidine derivatives were characterized by FT-IR, 1H NMR, 13C NMR spectral and elemental analysis. Further, the in vitro anti-breast cancer activity was evaluated by performing cytotoxicity studies against MCF-7 cell lines at different concentrations of synthesized compounds ranging from 100 to 500 µg/mL. Among the series of compounds, compounds 5a and 5d showed significant cytotoxic effect at the lowest concentration. However, all the synthesized compounds proved to be efficient against inhibiting breast cancer cells.

Keywords

Pyrazolo[3,4-d]-pyrimidines Microwave method Ionic liquid p-TSA L-Proline MCF-7 Breast cancer cell lines
Yallappa, G. N., Singh, L. P., Mounika, N., Cisma, V., Sattu, H., Panigrahy, U. P., … Muralidharan, V. (2024). Ionic Liquid Catalyzed Microwave Assisted Synthesis, Characterization and Anticancer Activity of Novel Pyrazolo[3,4-d]pyrimidine Derivatives. Asian Journal of Chemistry, 36(12), 2972–2976. https://doi.org/10.14233/ajchem.2024.32811
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. T. Chandra, N. Garg, S. Lata, K.K. Saxena and A. Kumar, Eur. J. Med. Chem., 45, 1772 (2010); https://doi.org/10.1016/j.ejmech.2010.01.009
  2. J.S. Chao, P.X. Hui, S. Li, Z.-Z. Qiu, P.-F. Xu, Z.-Y. Zhang, Q. Wang and Z.-W. Guan, J. Chinese Chem. Soc., 52, 539 (2005); https://doi.org/10.1002/jccs.200500079
  3. Q. Chen, X.-L. Zhu, L.-L. Jiang, Z.-M. Liu and G.-F. Yang, Eur. J. Med. Chem., 43, 595 (2008); https://doi.org/10.1016/j.ejmech.2007.04.021
  4. R.N. Rao and K. Chanda, Bioorg. Chem., 99, 103801 (2020); https://doi.org/10.1016/j.bioorg.2020.103801
  5. N.N. Makhova, M.I. Pleshchev, M.A. Epishina and A.S. Kulikov, Chem. Heterocycl. Comp., 50, 634 (2014); https://doi.org/10.1007/s10593-014-1516-1
  6. S. Zangade and P. Patil, Curr. Org. Chem., 23, 2295 (2019); https://doi.org/10.2174/1385272823666191016165532
  7. M.-Y. Li, A. Gu, J. Li and Y. Liu, Green Synth. Catal. (2024); https://doi.org/10.1016/j.gresc.2024.11.001
  8. G. Graziano, A. Stefanachi, M. Contino, R. Prieto-Díaz, A. Ligresti, P. Kumar, A. Scilimati, E. Sotelo and F. Leonetti, Int. J. Mol. Sci., 24, 6581 (2023); https://doi.org/10.3390/ijms24076581
  9. A. Adhikari, S. Bhakta and T. Ghosh, Tetrahedron, 126, 133085 (2022); https://doi.org/10.1016/j.tet.2022.133085
  10. M. Decker, Mini-Rev. Med. Chem., 7, 221 (2007); https://doi.org/10.2174/138955707780059817
  11. R. Morphy and Z. Rankovic, J. Med. Chem., 48, 6523 (2005); https://doi.org/10.1021/jm058225d
  12. Y. Zhang, C. Wu, N. Zhang, R. Fan, Y. Ye and J. Xu, Int. J. Mol. Sci., 24, 12724 (2023); https://doi.org/10.3390/ijms241612724
  13. C. Fraser, J.C. Dawson, R. Dowling, D.R. Houston, J.T. Weiss, A.F. Munro, M. Muir, L. Harrington, S.P. Webster, M.C. Frame, V.G. Brunton, E.E. Patton, N.O. Carragher and A. Unciti-Broceta, J. Med. Chem., 59, 4697 (2016); https://doi.org/10.1021/acs.jmedchem.6b00065
  14. K. Kandhasamy, R.R. Surajambika and P.K. Velayudham, Med. Chem., 20, 293 (2023); https://doi.org/10.2174/0115734064251256231018104623
  15. S. Dhawan, N. Kerru, P. Awolade, A. Singh-Pillay, S.T. Saha, M. Kaur, S.B. Jonnalagadda and P. Singh, Bioorg. Med. Chem., 26, 5612 (2018); https://doi.org/10.1016/j.bmc.2018.10.006
  16. T.S. Reddy, H. Kulhari, V. Ganga Reddy, V. Bansal, A. Kamal and R. Shukla, Eur. J. Med. Chem., 101, 790 (2015); https://doi.org/10.1016/j.ejmech.2015.07.031
  17. A.M. El-Morsy, M.S. El-Sayed and H.S. Abulkhair, Open J. Med. Chem., 7, 1 (2017); https://doi.org/10.4236/ojmc.2017.71001
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0