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Design, Synthesis, and Anticancer Activity of New Quinazoline Derivatives Containing Acetylhydrazide Moiety as EGFR Inhibitors and Apoptosis Inducers

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Abstract

Novel fuoryl quinazoline compounds were synthesized and assessed for anti-cancer efficacy. To varying degrees, all drugs exhibited cytotoxic effect against the test strains. Compound (VIIIc) had the highest IC50 values on MCF7 and HCT116 cell lines, with 25.43 to 23.69 µM, respectively. Compound (VIIIc) shows potent inhibitory activity towards EGFR. Flow cytometric studies revealed that compound (VIIIc) was capable of inducing G2/M arrest with a strong apoptotic effect.

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REFERENCES

  1. WHO Report on Cancer, 2020, pp. 1–160. https://apps.who.int/iris/rest/bitstreams/1267643/ retrieve.

  2. Zhan, Z., Wang, M., Zhang, C., Zhang, Z., Lu, J., and Wang, F., Chem. Commun., 2015, vol. 51, pp. 9205–9207. https://doi.org/10.1039/C5CC02785C

    Article  CAS  Google Scholar 

  3. Madhavi, S., Sreenivasulu, R., Yazala, J.P., and Raju, R.R., Saudi Pharm. J., 2017, vol. 25, pp. 275–279. https://doi.org/10.1016/j.jsps.2016.06.005

    Article  PubMed  Google Scholar 

  4. Conconi, M.T., Marzaro, G., Urbani, L., Zanusso, I., Di Liddo, R., Castagliuolo, I., Brun, P., Tonus, F., Ferrarese, A., Guiotto, A., and Chilin, A., Eur. J. Med. Chem., 2013, vol. 67, pp. 373–383. https://doi.org/10.1016/j.ejmech.2013.06.057

    Article  CAS  PubMed  Google Scholar 

  5. Alafeefy, A.M., Kadi, A.A., Al-Deeb, O.A., El-Tahir, K.E., and Al-Jaber, N.A., Eur. J. Med. Chem., 2010, vol. 45, pp. 4947–4952. https://doi.org/10.1016/j.ejmech.2010.07.067

    Article  CAS  PubMed  Google Scholar 

  6. Wang, H.J., Wei, C.X., Deng, X.Q., Li, F.L. and Quan, Z.S, Arch. Pharm., 2009, vol. 342, pp. 671–675. https://doi.org/10.1002/ardp.200900119

    Article  CAS  Google Scholar 

  7. Georgey, H., Abdel-Gawad, N., and Abbas, S., Molecules, 2008, vol. 13, pp. 2557–2569. https://doi.org/10.3390/molecules13102557

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Kasibhatla, S., Baichwal, V., Cai, S.X., Roth, B., Skvortsva, I., Skvortsov, S., Lucas, P., English, N. M., Sirisoma, N., Drewe, J., Pervin, A., Tseng, B., Carlson, R.O., and Pleiman, C.M., Cancer Res., 2007, vol. 67, pp. 5865–5871. https://doi.org/10.1158/0008-5472.CAN-07-0127

    Article  CAS  PubMed  Google Scholar 

  9. Chandrika, P.M., Yakaiah, T., Rao, A.R.R., Narsaiah, B., Reddy, N.C., Srindar, V., and Rao, J.V., Eur. J. Med. Chem., 2008, vol. 43, pp. 846–852. https://doi.org/10.1016/j.ejmech.2007.06.010

    Article  CAS  PubMed  Google Scholar 

  10. Sirisom, N., Pervin, A., Zhan, H., Jiang, S., Willardsen, J. A., Anderson, M.B., Mather, G., Pleiman, C.M., Kasibhatla, S., Tseng, B., Drewe, J., and Cai, S. X., J. Med. Chem., 2009, vol. 52, pp. 2341–2351. https://doi.org/10.1021/jm801315b

    Article  CAS  Google Scholar 

  11. Al-Obaid, A. M., Abdel-Hamide, S.G.A., El-Kashef, H. A., Abdel-Aziz, A. A-M., El-Azad, A. S., Al-Khamee, H. A., and El-Subbagh, H. I., Eur. J. Med. Chem., 2009, vol. 44, pp. 2379–2391. https://doi.org/10.1016/j.ejmech.2008.09.015

    Article  CAS  PubMed  Google Scholar 

  12. Font, M., Gonzalez, A., Palop, J.A., and Sanmartin, C., Eur. J. Med. Chem., 2011, vol. 46, pp. 3887–2899. https://doi.org/10.1016/j.ejmech.2011.05.060

    Article  CAS  PubMed  Google Scholar 

  13. Noolvi, M.N., Patel, H.M., Bhardwaj, V., and Chauhan, A., Eur. J. Med. Chem., 2011, vol. 46, pp. 2327–2346. https://doi.org/10.1016/j.ejmech.2011.03.015

    Article  CAS  PubMed  Google Scholar 

  14. Ahmed, M.F. and Belal, A., Res. Chem. Intermed., 2016, vol. 42, pp. 659–671. https://doi.org/10.1007/s11164-015-2048-8

    Article  CAS  Google Scholar 

  15. Ahmed, M.F., Belal, A., and Youns, M., Med. Chem. Res., 2015, vol. 24, pp. 2993–3007. https://doi.org/10.1007/s00044-015-1357-1

    Article  CAS  Google Scholar 

  16. Ahmed, M.F. and Hashim, A.A.A., Res. Chem. Intermed., 2016, vol. 42, pp. 1777–1789. https://doi.org/10.1007/s11164-015-2117-z

    Article  CAS  Google Scholar 

  17. Ahmed, M.F. and Belal, A., Arch. Pharm. Chem. Life Sci., 2015, vol. 348, pp. 487–497. https://doi.org/10.1002/ardp.201400468

    Article  CAS  Google Scholar 

  18. Alagarsamy, V., Solomon, V.R., Sheorey, R.V., and Jayakumar, R., Chem. Biol. Drug, Des., 2009, vol, 73, pp. 471–479. https://doi.org/10.1111/j.1747-0285.2009.00794.x

    Article  CAS  PubMed  Google Scholar 

  19. Smits, R.A., Adami, M., Istyastono, E.P., Zuiderveld, O.P., van Dam, C.M.E., de Kanter, F.J.J., Jongejan, A., Coruzzi, G., Leurs, R., and de Esch, I.J., J. Med. Chem., 2010, vol. 53, pp. 2390–2400. https://doi.org/10.1021/jm901379s

    Article  CAS  PubMed  Google Scholar 

  20. Held, F.E., Guryev, A.A., Fröhlich, T., Hampel, F., Kahnt, A., Hutterer, C., Steingruber, M., Bahsi, H., von Bojničić-Kninski, C., Mattes, D.S., and Foertsch, T.C., Nature Comm., 2017, vol. 8, pp. 1–9. https://doi.org/10.1038/ncomms15071

    Article  Google Scholar 

  21. Raghavendra, N.M., Thampi, P., Gurubasavarajaswamy, P.M., and Sriramm D., Chem. Pharm. Bull., 2007, vol. 55, pp. 1615–1619. https://doi.org/10.1248/cpb.55.1615

    Article  CAS  Google Scholar 

  22. Das, D. and Hong, J., Eur. J. Med. Chem., 2019, vol. 170, pp. 55–72. https://doi.org/10.1016/j.ejmech.2019.03.004

    Article  CAS  PubMed  Google Scholar 

  23. Ahmed, M. and Magdy, N., Acta Pol. Pharm., 2018, vol. 75, pp. 1321–1328. https://doi.org/10.32383/appdr/89488

    Article  CAS  Google Scholar 

  24. Ahmed, M. and Magdy, N., Acta Pol. Pharm., 2018, vol. 75. https://doi.org/10.32383/appdr/89488

  25. He, Y.Y., Huang, J.L., and Chignell, C.F., Oncogene, 2006, vol. 25, pp. 1521–1531. https://doi.org/10.1038/sj.onc.1209184

    Article  CAS  PubMed  Google Scholar 

  26. Bae, S.S., Choi, J.H., Oh, Y.S., Perry, D.K., Ryu, S.H., and Suh, P.G., FEBS Lett., 2001, vol. 491, pp. 16–20. https://doi.org/10.1016/S0014-5793(01)02167-6

    Article  CAS  PubMed  Google Scholar 

  27. Zhang, J., Ren, D., Ma, Y., Wang, W., Wu, H., Tetrahedron, 2014, vol. 70, pp. 5274–5282. https://doi.org/10.1016/j.tet.2014.05.059

    Article  CAS  Google Scholar 

  28. Manning, G., Whyte, D.B., Martinez, R., Hunter, T., and Sudarsanam, S., Science, 2002, vol. 298, pp. 1912–1934. https://doi.org/10.1126/science.1075762

    Article  CAS  PubMed  Google Scholar 

  29. Grant, S.K., Cell. Mol. Life Sci., 2009, vol. 66, pp. 1163–1177. https://doi.org/10.1007/s00018-008-8539-7

    Article  CAS  PubMed  Google Scholar 

  30. Wu, Q., Zheng, K., Huang, X., Li, L., and Mei, W., J. Med. Chem., 2018, vol. 61, pp. 10488–10501. https://doi.org/10.1021/acs.jmedchem.8b01018

    Article  CAS  PubMed  Google Scholar 

  31. Ahmed, M.F., Santali, E.Y., and El-Haggar, R., J. Enzyme Inhib. Med. Chem., 2021, vol. 36, pp. 307–318. https://doi.org/10.1080/14756366.2020.1861606

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, College of Pharmacy, Taif University, P.O. Box 11099, 21944, Taif, Saudi Arabia

    Reem I. Alsantali

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Correspondence to Reem I. Alsantali.

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ACKNOWLEDGMENT

The researchers would like to acknowledge Deanship of Scientific Research, Taif University for funding this work.

COMPLIANCE WITH ETHICAL STANDARDS

The author declares that he has no conflicts of interest.

This article does not contain any studies involving animals or human participants performed by any of the authors.

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Alsantali, R.I. Design, Synthesis, and Anticancer Activity of New Quinazoline Derivatives Containing Acetylhydrazide Moiety as EGFR Inhibitors and Apoptosis Inducers. Russ J Bioorg Chem 49, 645–654 (2023). https://doi.org/10.1134/S1068162023030044

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