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Synthesis of Novel 1,3,4-Oxadiazole-functionalized Trifluoromethyl-pyrido[2,3-d]pyrimidine Derivatives and Their Anticancer Activity

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Abstract

Novel 1,3,4-oxadiazole-functionalized pyrido[2,3-d]pyrimidine derivatives were prepared starting from 2-amino-6-(thiophen-2-yl)-4-(trifluoromethyl)nicotinonitrile, which was reacted with trifluoroacetic acid in the presence of conc. H2SO4 and further with bromoethyl acetate to obtain ethyl 2-{4-oxo-7-(thiophen-2-yl)-2,5-bis(trifluoromethyl)pyrido[2,3-d]pyrimidin-3(4H)-yl}acetate. The reaction of the latter products with hydrazine hydrate gave 2-{4-oxo-7-(thiophen-2-yl)-2,5-bis(trifluoromethyl)pyrido[2,3-d]pyrimidin-3(4H)-yl}acetohydrazide. The subsequent treatment of the products with a series of aromatic acids resulted in the synthesis of 3-[(5-aryl-1,3,4-oxadiazol-2-yl)methyl]-7-(thiophen-2-yl)-2,5-bis(trifluoromethyl)pyrido[2,3-d]pyrimidin-4(3H)-ones and 2-aryl-5-({[7-(thiophen-2-yl)-2,5-bis(trifluoromethyl)pyrido[2,3-d]pyrimidin-4-yl]oxy}methyl)-1,3,4-oxadiazoles. All the synthesized final products were tested for anticancer activity against 4 human cancer cell lines: such as A549-Lung cancer (CCL-185), MCF7-Breast cancer (HTB-22), DU145-Prostate cancer (HTB-81), and HeLa-Cervical cancer (CCL-2). Some of the tested compounds showed promising anticancer activity.

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REFERENCES

  1. Puthiyapurayil, P., Poojary, B., Chikkanna, C., and Buridipad, S.K., Eur. J. Med. Chem., 2012, vol. 53, p. 203. https://doi.org/10.1016/j.ejmech.2012.03.056

    Article  CAS  PubMed  Google Scholar 

  2. Burova, O.A., Bystrykova, I.D., Smirnova, N.M., and Safonova, T.S., Chem Heterocycl. Compd., 1991, vol. 27, p. 394. https://doi.org/10.1007/BF00480837

    Article  Google Scholar 

  3. Rahman, L.K.A. and Chhabra, S.R., Med. Res. Rev., 1988, vol. 8, p. 95. https://doi.org/10.1002/med.2610080106

    Article  CAS  PubMed  Google Scholar 

  4. Gangjee, A., Vasudevan, A., Queener, F., and Kisliuk, R., J. Med. Chem., 1996, vol. 39, p. 1438. https://doi.org/10.1021/jm950786p

    Article  CAS  PubMed  Google Scholar 

  5. Zink, M., Lanig, H., and Troschutz, R., Eur. J. Med. Chem., 2004, vol. 39, p. 1079. https://doi.org/10.1016/j.ejmech.2004.09.001

    Article  CAS  PubMed  Google Scholar 

  6. Cordeu, L., Cubedo, E., and Bandres, E., Bioorg. Med. Chem., 2007, vol. 15, p. 1659. https://doi.org/10.1016/j.bmc.2006.12.010

    Article  CAS  PubMed  Google Scholar 

  7. Monge, V.A., Martinez, M.V., Sanmartin, G.C., and Simon, A.M.A., Spa. Patent ES 2056742 A1, 1994; Chem. Abstr., 1995, vol. 122, no. 105912q.

  8. Parmar, K., Suthar, B., Suthar, A., and Maheta, A., J. Heterocycl. Chem., 2009, vol. 46, p. 975. https://doi.org/10.1002/jhet.190

    Article  CAS  Google Scholar 

  9. Koeckkritz, P., Ruhmann, C., Fieblinger, D., Schroeder, C., Joksch, B., Heider, H., Weiher, B., and Liebscher, J., Ger. Patent no. DE 4117802 A1, 1992.

  10. Narayana, B., Ram Rao, A., and Shanthan Rao, P., Eur. J. Med. Chem., 2009, vol. 44, p. 1369. https://doi.org/10.1016/j.ejmech.2008.05.025

    Article  CAS  Google Scholar 

  11. Kashyap, D., Tuli, H.S., and Sharma, A.K., Life Sci., 2016, vol. 146, p. 201. https://doi.org/10.1016/j.lfs.2016.01.017

    Article  CAS  PubMed  Google Scholar 

  12. Salvador, J.A.R., Leal, A.S., Valdeira, A.S., Gonçalves, B.M.F., Alho, D.P.S., Figueiredo, S.A.C., Silvestre, S.M., and Mendes, V.I.S., Eur. J. Med. Chem., 2017, vol. 142, p. 95. https://doi.org/10.1016/j.ejmech.2017.07.013

    Article  CAS  PubMed  Google Scholar 

  13. Cháirez-Ramirez, M.H., Moreno-Jiménez, M.R., González-Laredo, R.F., Gallegos-Infante, J.A., and Rocha-Guzmán, N.E., EXCLI J., 2016, vol. 15, p. 758. https://doi.org/10.17179/excli2016-642

    Article  PubMed  PubMed Central  Google Scholar 

  14. Ma, X., Zhang, y., Wang, Z., Shen, Y., Zhang, M., Nie, Q., Hou, Y., and Bai, G., Mol. Nutr. Food Res., 2017, vol. 61, p. 1700332. https://doi.org/10.1002/mnfr.201700332

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Puthiyapurayil, P., Poojary, B., Chikkanna, C., and Buridipad, S.K., Eur. J. Med. Chem., 2012, vol. 53, p. 203. https://doi.org/10.1016/j.ejmech.2012.03.056

    Article  CAS  PubMed  Google Scholar 

  16. Song, M.X., Zheng, C.J., Deng, X.Q., Sun, L.P., Wu, Y., Hong, L., Li, Y.J., Liu, Y.Z., Wei, Y., Jin, M.J., and Piao, H.R., Eur. J. Med. Chem., 2013, vol. 60, p. 376. https://doi.org/10.1016/j.ejmech.2012.12.007

    Article  CAS  PubMed  Google Scholar 

  17. de Oliveira, C.S., Lira, B.F., Barbosa-Filho, J.M., Lorenzo, J.G.F., and de Athayde-Filho, P.F., Molecules, 2012, vol. 17, p. 10192. https://doi.org/10.3390/molecules170910192

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Liu, Z., Zhao, J., and Huang, X., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 1828. https://doi.org/10.1016/j.bmcl.2006.01.002

    Article  CAS  PubMed  Google Scholar 

  19. Porta, F., Facchetti, G., Ferri, N., Gelain, A., Meneghetti, F., Villa, S., Barlocco, D., Masciocchi, D., Asai, A., Miyoshi, N., and Marchianò, S., Eur. J. Med. Chem., 2017, vol. 131, p. 196. https://doi.org/10.1016/j.ejmech.2017.03.017

    Article  CAS  PubMed  Google Scholar 

  20. Mihailović, N., Marković, V., Matić, I.Z., Stanisavljević, N.S., Jovanović, Ž.S., Trifunović, S., and Joksović, L., RSC Adv., 2017, vol. 7, p. 8550. https://doi.org/10.1039/C6RA28787E

    Article  Google Scholar 

  21. Wang, P.Y., Zhou, L., Zhou, J., Fang, H.S., Wu, Z.B., Xue, W., Song, B.A., and Yang, S., Chem. Pap., 2017, vol. 71, p. 1013. https://doi.org/10.1007/s11696-016-0021-7

    Article  CAS  Google Scholar 

  22. Gan, X., Hu, D., Chen, Z., Wang, Y., and Song, B., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 4298. https://doi.org/10.1016/j.bmcl.2017.08.038

    Article  CAS  PubMed  Google Scholar 

  23. Rathore, A., Sudhakar, R., Ahsan, M.J., Ali, A., Subbarao, N., Jadav, S.S., Umar, S., and Yar, M.S., Bioorg. Chem., 2017, vol. 70, p. 107. https://doi.org/10.1016/j.bioorg.2016.11.014

    Article  CAS  PubMed  Google Scholar 

  24. Liu, Q., Zhu, R., Gao, S., Ma, S.H., Tang, H.J., Yang, J.J., Diao, Y.M., Wang, H.L., and Zhu, H.J., Pest Manag. Sci., 2017, vol. 73, p. 917. https://doi.org/10.1002/ps.4363

    Article  CAS  PubMed  Google Scholar 

  25. Patel, N.B., Patel, J.N., Purohit, A.C., Patel, V.M., Rajani, D.P., Moo-Puc, R., Lopez-Cedillo, J.C., Nogueda-Torres, B., and Rivera, G., Int. J. Antimicrob. Agents, 2017, vol. 50, p. 413. https://doi.org/10.1016/j.ijantimicag.2017.04.016

    Article  CAS  PubMed  Google Scholar 

  26. Narsaiah, B., Sivaprasad, A., and Venkataratnam, R.V., J. Fluorine Chem., 1994, vol. 67, p. 87. https://doi.org/10.1016/0022-1139(93)02936-9

    Article  CAS  Google Scholar 

  27. Mosmann, T., J. Immunol. Methods, 1983, vol. 65, p. 55. https://doi.org/10.1016/0022-1759(83)90303-4

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. GITAM (Deemed to be University), Department of Chemistry, 502329, Hyderabad, India

    M. M. Kumar, B. R. Reddy, K. Balakrishna & G. Rambabu

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  1. M. M. Kumar
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  2. B. R. Reddy
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  3. K. Balakrishna
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  4. G. Rambabu
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Correspondence to K. Balakrishna or G. Rambabu.

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Kumar, M.M., Reddy, B.R., Balakrishna, K. et al. Synthesis of Novel 1,3,4-Oxadiazole-functionalized Trifluoromethyl-pyrido[2,3-d]pyrimidine Derivatives and Their Anticancer Activity. Russ J Org Chem 59, 870–876 (2023). https://doi.org/10.1134/S1070428023050172

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