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.
Similar content being viewed by others
REFERENCES
Ahaluwalia, V.K., Dutta, U., Sharma, H.R., Indian J. Chem. Sect. B, 1987, vol. 26, p. 88.
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
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
Behalo, M.S., Mele, G., J. Hetercycl. Chem., 2017, vol. 54, pp. 295–300. https://doi.org/10.1002/jhet.2581
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
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
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
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
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
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.
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.
Khokhani, K., Khatri, T., Ram, V., and Patel, P., Chem. Biol. Int., 2013, vol. 3, no. 3, pp. 192–200.
Suresh, M., Lavanya, P., Vasu, K., Sudhakar, D., Rao, C.V., J. Chem. Pharm. Res., 2010, vol. 2, no. 2, pp. 82–89.
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
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
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
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
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.
Robins, R.K. and Hitchings, G.H.J., Am. Chem. Soc., 1958, vol. 80, pp. 3449–3457.
Madkour, H.M.F., Saleem, M.A.I., Abdel-Rahman, T.M., and Azab, M.E., Heterocycles, 1994, vol. 38, pp. 57–69.
Lowe, J.A., Chem. Abstr. 112, 1990, 21008 Austrian At. 388378 (1989) 378.
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
Iwamura, H., Murakami, S., Koshimizu, K., and Matsabura, S., J. Med. Chem., 1985, vol. 28, pp. 577–583.
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
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
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
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
Perez, C., Paul, M., and Bazerque, P., Acta. Bio. Med. Exp., 1990, vol. 15, pp. 113–115.
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
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
NCCLS, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, Which Grow Aerobically, 5th ed., Approved Standard M7-A5, NCCLS, Villanova, PA, 2000.
ACKNOWLEDGMENTS
The authors would like to acknowledge Dr. Doaa Ghareeb, Biochemistry Department, Faculty of Science, Alexandria University for her help in biological activity work.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
COMPLIANCE WITH ETHICAL STANDARDS
This article does not contain any research involving humans or animals as research subjects.
Conflict of Interests
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1068162021020114