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Synthesis and Biological Activity Studies of Novel Pyrido[2,3-d]pyrimidines and Pyrido[2,3-d]triazines

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Abstract

Novel derivatives of pyrido[2,3-d]pyrimidin-2,4(1H,3H)-dithione, 2,3-dimethylpyrido[2,3-d]pyrimidin-4-one, 4-chloro-2-methypyrido[2,3-d]pyrimidine and pyrido[2,3-d]1,2,3 triazin-4-one were synthesized and screened for their anti-microbial and cytoxic activities. 5,7-diphenyl-pyrido[2,3-d]pyrimidin-2,4(1H,3H)-dithione, 5-(4-methoxyphenyl)-7-phenyl-pyrido[2,3-d]pyrimidin-2,4(1H,3H)–dithione, 5,7-diphenyl-2,3-dimethylpyrido[2,3-d]pyrimidin-4-one, 4-chloro-5,7-diphenyl-2-methypyrido[2,3-d]pyrimidine, 4-chloro-7-(4-chlorophenyl)-5-phenyl-2-methypyrido[2,3-d]pyrimidine, 5,7-diphenyl-3,4-dihydropyrido[2,3-d]1,2,3-triazin-4-one, 5-(4-methoxyphenyl)-7-phenyl-3,4-dihydropyrido[2,3-d]1,2,3-triazin-4-one and 7-(4-chlorophenyl)-5-phenyl-3,4-dihydropyrido[2,3-d]1,2,3-triazin-4-one showed excellent anti-microbial activities against all the tested bacteria and fungi compared to the reference drugs. Furthermore, they exhibited high safety profile in cytotoxicity test except 5,7-diphenyl-2,3-dimethylpyrido[2,3-d]pyrimidin-4-one and 4-chloro-7-(4-chlorophenyl)-5-phenyl-2-methypyrido[2,3-d]pyrimidine. The structures of the newly synthesized compounds were confirmed by spectral data and elemental analysis.

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REFERENCES

  1. Ahaluwalia, V.K., Dutta, U., Sharma, H.R., Indian J. Chem. Sect. B, 1987, vol. 26, p. 88.

    Google Scholar 

  2. Abbas, S.E., George, R.F., Samir, E.M., Aref, M.M., and Abdel-Aziz, H.A., Future Med. Chem., 2019, vol. 11, no. 18, pp. 2395–2414. https://doi.org/10.4155/fmc-2019-0050

    Article  CAS  PubMed  Google Scholar 

  3. Elzahabi, H.S., Nossier, E.S., Khalifa, N.M., Alasfoury, R.A., El-Manawaty, M.A., J. Enz. Inhib. Med. Chem., 2018, vol. 33, no. 1, pp. 546–557. https://doi.org/10.1080/14756366.2018.1437729

    Article  CAS  Google Scholar 

  4. Behalo, M.S., Mele, G., J. Hetercycl. Chem., 2017, vol. 54, pp. 295–300. https://doi.org/10.1002/jhet.2581

    Article  CAS  Google Scholar 

  5. Kurumurthy, C., Rao, P.S., Swamy, B.V., Kumar, G.S., Rao, P.S., Narsaiah, B., Velatooru, L.R., Pamanji, R., and Rao, J.V., Eur. J. Med. Chem., 2011, vol. 46, no. 8, pp. 3462–3468. https://doi.org/10.1016/j.ejmech.2011.05.011

    Article  CAS  PubMed  Google Scholar 

  6. Elagamey, A.G., Abdel Sattar, S., El-Taweel, F., and Said, S., J. Heterocycl. Chem., 2016, vol. 53, no. 6, pp. 1801–1806. https://doi.org/10.1002/jhet.2487

    Article  CAS  Google Scholar 

  7. Narayana, B.L., Rao, A.R., Rao, P.S., Eur. J. Med. Chem., 2009, vol. 44, no. 3, pp. 1369–1376. https://doi.org/10.1016/j.ejmech.2008.05.025

    Article  CAS  Google Scholar 

  8. Kanth, S.R., Reddy, G.V., Kishore, K.H., Rao, P.S., Narsaiah, B., and Murthy, U.S.N., Eur. J. Med. Chem., 2006, vol. 41, no. 8, pp. 1011–1016. https://doi.org/10.1016/j.ejmech.2006.03.028

    Article  CAS  Google Scholar 

  9. Tiwari, S., Yadav, A.K., and Mishra, A.K., E.-J. Chem., 2010, vol. 7, no. S1, pp. S85–S92. https://doi.org/10.1155/2010/812567

    Article  CAS  Google Scholar 

  10. Kumar, N., Tiwari, S., and Yadav, A.K., Indian J. Chem., 2007, vol. 46B, pp. 702–706. http://nopr.niscair.res.in/handle/123456789/664.

    CAS  Google Scholar 

  11. Shanmugasundaram, P., Harikrishnan, N., Aanandini, M.V., Kumar M.S., and Sateesh, J.N., Indian J. Chem., 2011, vol. 50B, no. 3, pp. 284–289. http://nopr.niscair.res.in/handle/123456789/11178.

    CAS  Google Scholar 

  12. Khokhani, K., Khatri, T., Ram, V., and Patel, P., Chem. Biol. Int., 2013, vol. 3, no. 3, pp. 192–200.

  13. Suresh, M., Lavanya, P., Vasu, K., Sudhakar, D., Rao, C.V., J. Chem. Pharm. Res., 2010, vol. 2, no. 2, pp. 82–89.

  14. Hanafy, F.I., Eur. J. Chem., 2011, vol. 2, no. 1, pp. 65–69. https://doi.org/10.5155/eurjchem.2.1.65-69.303

    Article  CAS  Google Scholar 

  15. Ibrahim, D.A. and Ismail, N.S.M., Eur. J. Med. Chem., 2011, vol. 46, no. 12, pp. 5825–5832. https://doi.org/10.1016/j.ejmech.2011.09.041

    Article  CAS  PubMed  Google Scholar 

  16. Gfesser, G.A., Bayburt, E.K., Cowart, M., DiDomenico, S., Gomtsyan, A., Lee, C., Stewart, A.O., Jarvis, M.F., Kowaluk, E.A., and Bhagwat, S.S., Eur. J. Med. Chem., 2003, vol. 38, no. 3, pp. 245–252. https://doi.org/10.1016/S0223-5234(03)00019-9

    Article  CAS  PubMed  Google Scholar 

  17. Zhang, H.J., Wang, S.B., Wen, X., Li, J.Z., and Quan, Z.S., Med. Chem. Res., 2016, vol. 25, pp. 1287–1298. https://doi.org/10.1007/s00044-016-1559-1

    Article  CAS  Google Scholar 

  18. Piper, J.R., Mc Calab, G.S., Montgomery, J.A., Kishiuk, R.L., Gamount, Y., and Sirotnak, F.M., J. Med. Chem., 1986, vol. 29, pp. 1080–1087.

    Article  CAS  Google Scholar 

  19. Robins, R.K. and Hitchings, G.H.J., Am. Chem. Soc., 1958, vol. 80, pp. 3449–3457.

    Article  CAS  Google Scholar 

  20. Madkour, H.M.F., Saleem, M.A.I., Abdel-Rahman, T.M., and Azab, M.E., Heterocycles, 1994, vol. 38, pp. 57–69.

    Article  CAS  Google Scholar 

  21. Lowe, J.A., Chem. Abstr. 112, 1990, 21008 Austrian At. 388378 (1989) 378.

  22. Gangjee, A., Adair, O.O., and Queener, S.F., J. Med. Chem., 2003, vol. 46, no. 23, pp. 5074–5082. https://doi.org/10.1021/jm030312n

    Article  CAS  PubMed  Google Scholar 

  23. Iwamura, H., Murakami, S., Koshimizu, K., and Matsabura, S., J. Med. Chem., 1985, vol. 28, pp. 577–583.

    Article  CAS  Google Scholar 

  24. Malagu, K., Duggan, H., Menear, K., Hummersone, M., Gomez, S., Bailey, C., Edwards, P., Drzewiecki, J., Leroux, F., Quesada, M.J., Hermann, G., Maine, S., Molyneaux, C., Gall, A.L., Pullen, J., Hickson, I., Smith, L., Maguire, S., Martin, N., Smith, G., and Pass, M., Bioorg. Med. Chem. Lett., 2009, vol. 19, no. 20, pp. 5950–5953. https://doi.org/10.1016/j.bmcl.2009.08.038

    Article  CAS  PubMed  Google Scholar 

  25. Moreno, E., Plano, D., Lamberto, I., Font, M., Encío, I., Palop, J.A., and Sanmartín, C., Eur. J. Med. Chem., 2012, vol. 47, pp. 283–298. https://doi.org/10.1016/j.ejmech.2011.10.056

    Article  CAS  PubMed  Google Scholar 

  26. Sanmartin, C., Echeverría, M., Mendívil, B., Cordeu, L., Cubedo, E., Foncillas, J.G., Font, M., and Palop, J.A., Bioorg. Med. Chem., 2005, vol. 13, no. 6, pp. 2031–2044. https://doi.org/10.1016/j.bmc.2005.01.008

    Article  CAS  PubMed  Google Scholar 

  27. Elsaedany, S.K., Zein, M.A.E, Abedel-Rehim, E.M., and Keshk, R.M., J. Heterocycl. Chem., 2016, vol. 53, pp. 1534–1543. https://doi.org/10.1002/jhet.2460

    Article  CAS  Google Scholar 

  28. Perez, C., Paul, M., and Bazerque, P., Acta. Bio. Med. Exp., 1990, vol. 15, pp. 113–115.

    Google Scholar 

  29. Dos Santos, K.S., Coelho, J.F., Ferreira, P., Pinto, I., Lorenzetti, S.G., Ferreira, E.I., Higa, O.Z., and Gil, M.H., Int. J. Pharm., 2006, vol. 310, pp. 37–45. https://doi.org/10.1016/j.ijpharm.2005.11.019

    Article  CAS  PubMed  Google Scholar 

  30. Yadav, A.K. and Gupta, M., Indian J. Chem., 2014, vol. 53B, no. 10, pp. 1247–1254. http://nopr.niscair.res.in/handle/123456789/29469

  31. NCCLS, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, Which Grow Aerobically, 5th ed., Approved Standard M7-A5, NCCLS, Villanova, PA, 2000.

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ACKNOWLEDGMENTS

The authors would like to acknowledge Dr. Doaa Ghareeb, Biochemistry Department, Faculty of Science, Alexandria University for her help in biological activity work.

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Correspondence to Reda Mohammed Keshk.

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Elsaedany, S.K., AbdEllatif zein, M., AbdElRehim, E.M. et al. Synthesis and Biological Activity Studies of Novel Pyrido[2,3-d]pyrimidines and Pyrido[2,3-d]triazines. Russ J Bioorg Chem 47, 552–560 (2021). https://doi.org/10.1134/S1068162021020114

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