Skip to main content
Log in

Synthesis and In Vitro Antitumor Activity of Novel Chromenones Bearing Benzothiazole Moiety

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

6-(Benzo[d]thiazol-2-yl)-4-oxo-(4H)-chromene-3-carbaldehyde was utilized to construct a novel series of fused chromone bearing benzothiazole moiety, namely chromeno[2,3-b]azetol, benzo[c]chromene, and chromeno[2,3-c]pyrazole derivatives, as well as, non-fused chromones, such as thiazolidinone, pyrazolone, and pyridine derivatives. The in vitro antitumor activities of the synthesized products against six cancer cell lines, including A594, HCT-116, MCF-7, HepPG2, PC3, and HFB4, were evaluated. Some compounds exhibited significant anticancer activities against both lung and colon cancer cells very close to that of a standard drug doxorubicin.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.

Similar content being viewed by others

REFERENCES

  1. Gottesman, M.M., Annu. Rev. Med., 2002, vol. 53, pp. 615–627.

    Article  CAS  PubMed  Google Scholar 

  2. Nobili, S., Landini, I., Giglioni, B., and Mini, E., Curr. Drug Targets, 2006, vol. 7, no. 7, pp. 861–879.

    Article  CAS  PubMed  Google Scholar 

  3. Li, J., Wang, X.L., Fang, Y.C., and Wang, C.Y., J. Asian Nat. Prod. Res., 2010, vol.12, no. 11, pp. 992–1000.

    Article  CAS  PubMed  Google Scholar 

  4. Patil, S. A., Wang, J., Li, X.S., Chen, J., Jones, T.S., Hosni-Ahmed, A., Patil, R., Seibel, W.L., Li, W., and Miller, D.D., Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 13, pp. 44–58.

    Google Scholar 

  5. Kandeel, M.M., Kamal, A.M., Abdelall, E.K.A., and Elshemy, H.A.H., Der Pharma Chemica, 2012, vol. 4, no. 4, pp. 1653–1661.

    CAS  Google Scholar 

  6. Thomas, N. and Zachariah, S.M., Asian J. Pharm. Clin. Res., 2013, vol. 6, suppl. 2, pp. 11–15.

    CAS  Google Scholar 

  7. Zonouzi, A., Mirzazadeh, R., Safavi, M., Ardestani, S.K., Emami, S., and Foroumadi, A., Iranian J. Pharm. Res. (IJPR),2013, vol. 12, no. 4, pp. 679–685.

    CAS  Google Scholar 

  8. Reddy, K.R., Rao, P.S., Dev, G.J., Poornachandra, Y., Kumar, C.G., Rao, P.S., and Narsaiah, B., Bioorg. Med. Chem. Lett., 2014, vol. 24, no. 7, pp. 1661–1663.

    Article  CAS  Google Scholar 

  9. Rahmani-Nezhad, S., Safavi, M., Pordeli, M., Ardestani, S.K., Khosravani, L., Pourshojaei, Y., Mahdavi, M., Emami, S., Foroumadi, A., and Shafiee, A., Eur. J. Med. Chem., 2014, vol. 86, pp. 562–569.

    Article  CAS  PubMed  Google Scholar 

  10. Fouad, S.A., Int. J. Adv. Res., 2014, vol. 2, no. 12, pp. 442–453.

    Google Scholar 

  11. Banerjee, S., Wang, J., Pfeffer, S., Ma, D., Pfeffer, L.M., Patil, S.A., Li, W., and Miller, D.D., Molecules, 2015, vol. 20, pp. 17152–17165.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Puppala, M., Zhao, X., Casemore, D., Zhou, B., Aridoss, G., Narayanapillai, S., and Xing, C., Bioorg. Med. Chem., 2016, vol. 24, no. 6, pp. 1292–1297.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Fouda, A.M., Med. Chem. Res., 2016, vol. 25, pp. 1229–1238.

    Article  CAS  Google Scholar 

  14. Salem, M.S., Marzouk, M.I., Ali, S.N., and Madkour, H.M. F., Eur. J. Chem., 2012, vol. 3, no. 2, pp. 220–227.

    Article  CAS  Google Scholar 

  15. Yadav, P.S., Devprakash, and Senthilkumar, G. P., Int. J. Pharm. Sci. Drug Res., 2011, vol. 3, no. 1, pp. 1–7.

    Google Scholar 

  16. Abbas, E.M.H., Salem, M.S., Kassem, A.F.M., Abd El-Moez, Sh.I., and El-Kady, M., Eur. J. Chem., 2015, vol. 6, no. 2, pp. 98–106.

    Article  CAS  Google Scholar 

  17. Kok, S.H., Gambari, R., Chui, C.H., Yuen, M.C.W., Lin, E., Wong, R.S.M., Lau, F.Y., Cheng, G.Y.M., Lam, W.S., Chan, S.H., Lam, K.H., Cheng, C.H., Lai, P.B.S., Yu, M.W.Y., Cheung, F., Tang, J.C.O.,and Chan, A.S.C., Bioorg. Med. Chem., 2008, vol. 16, no. 7, pp. 3626–3631.

    Article  CAS  PubMed  Google Scholar 

  18. Havrylyuk, D., Mosula, L., Zimenkovsky, B., Vasylenko, O., Gzella, A., and Lesyk, R., Eur. J. Med. Chem., 2010, vol. 45, no. 11, pp. 50125021.

  19. Devmurari, V.P., Shivanand, P., Goyani, M.B., Nandanwar, R.R., Jivani, N.P., and Perumal, P. Int. J. Chem. Tech. Res., 2010, vol. 2, no. 1, pp. 681–689.

    CAS  Google Scholar 

  20. Furlan, A., Colombo, F., Kover, A., Issaly, N., Tintori, C., Angeli, L., Leroux, V., Letard, S., Amat, M., Asses, Y., Maigret, B., Dubreuil, P., Botta, M., Dono, R., Bosch, J., Piccolo, O., Passarella, D., and Maina, F., Eur. J. Med. Chem., 2012, vol. 47, pp. 239–254.

    Article  CAS  PubMed  Google Scholar 

  21. Shi, X., Wang, Z., Xia, Y., Ye, T., Deng, M., Xu, Y., Wei, Y., and Yu, L., Molecules, 2012, vol. 17, pp. 3933–3944.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Caputo, R., Calabrò, M.L., Micale, N., Schimmer, A.D., Ali, M., Zappalà, M., and Grasso, S., Med. Chem. Res., 2012, vol. 21, no. 9, pp. 2644–2651.

    Article  CAS  Google Scholar 

  23. Lindgren, E.B., de Brito, M.A., Vasconcelos, T.R.A., de Moraes, M.O., Montenegro, R.C., Yoneda, J.D., and Leal, K.Z., Eur. J. Med. Chem., 2014, vol. 86, pp. 12–16.

    Article  CAS  PubMed  Google Scholar 

  24. Gurdal, E.E., Buclulgan, E., Durmaz, V., Cetin-Atalay, R., and Yarim, M., Anticancer Agents Med. Chem., 2015, vol. 15, no. 3, pp. 382–389.

    Article  CAS  PubMed  Google Scholar 

  25. El-Damasy, A.K., Lee, J.H., Seo, S.H., Cho, N.C., Pae, A.N., and Keum, G., Eur. J. Med. Chem., 2016, vol. 115, pp. 201–216.

    Article  CAS  PubMed  Google Scholar 

  26. Singh, M., Singh, S.K., Thakur, B., Ray, P., and Singh, S.K., Anticancer Agents Med. Chem., 2016, vol. 16, no. 6, pp. 722–739.

    Article  CAS  PubMed  Google Scholar 

  27. Meenakshi, S., Arusha, M., Gopeshwar, N., and Sushil, S.K., Anti-Cancer Drugs, 2016, vol. 27, no. 6, pp. 519–532.

    Article  CAS  Google Scholar 

  28. Mohamed, K.S., Refat, H.M., and Mohamed, N.A.H., Heterocycles, 2016, vol. 92, no. 8, pp. 1415–1429.

    Article  CAS  Google Scholar 

  29. Bozdag-Dundar, O., Evranos, B., Das-Evcimen, N., Sarhkaya, M., and Ertan, R., Eur. J. Med. Chem., 2008, vol. 43, no. 11, pp. 24122417.

  30. Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Day, C.W., Smee, D.F., Grellier, P., and Lesyk, R., Eur. J. Med. Chem., 2013, vol. 66, pp. 228–237.

    Article  CAS  PubMed  Google Scholar 

  31. Kapoor, G., Pathak, D.P., Bhutani, R., and Kant, R., J. Chem. Pharm. Res., 2016, vol. 8, no. 4, pp. 151–168.

    CAS  Google Scholar 

  32. Salem, M.S., and Ali, M.A.M., Biol. Pharm. Bull., 2016, vol. 39, pp. 473–483.

    Article  CAS  PubMed  Google Scholar 

  33. El-Hashash, M.A.M., Salem, M.S., and Al-Mabrook, S.A.M., Res. Chem. Intermed., 2018, vol. 44, pp. 2545–2559.

    Article  CAS  Google Scholar 

  34. Pal, D., Saha, S., and Singh, S., Int. J. Pharm. Pharm. Sci., 2012, vol. 4, no. 2, pp. 98104.

  35. Jamwal, A., Javed, A., and Bhardwaj, V., J. Pharm. Bio. Sci., 2014, vol. 3, pp. 114–123.

    Google Scholar 

  36. Ali, A.R., El-Bendary, E.R., Ghaly, M.A., and Shehata, I.A., Eur. J. Med. Chem., 2014, vol. 75, pp. 492–500.

    Article  CAS  PubMed  Google Scholar 

  37. Lacova, M., Loos, D., Furdik, M., Matulova, M., and El-Shaaer, H.M., Molecules, 1998, vol. 3, pp. 149–158.

    Article  CAS  Google Scholar 

  38. Hu, K., Yang, Z., Pan, S., Xu, H., and Ren, J., Eur. J. Med. Chem., 2010, vol. 45, pp. 3453–3458.

    Article  CAS  PubMed  Google Scholar 

  39. Altıntop, M.D., Temel, H.E., Sever, B., Çiftçi, G.A., and Kaplancıkl, Z.A., Molecules, 2016, vol. 2, pp. 1598–1617.

    Article  CAS  Google Scholar 

  40. Hassan, G., El-Messry, S., Al-Omary, F., and El-Sabbagh, H., Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 20, pp. 6318–6323.

    Article  CAS  PubMed  Google Scholar 

  41. Amit, C., Sheelmani, S.A., Payal, C., and Dhawan, R.K. Adv. J. Pharm. Life Sci. Res., 2014, vol. 2, no. 1, pp. 1–7.

    Google Scholar 

  42. Spanò, V., Attanzio, A., Cascioferro, S., Carbone, A., Montalbano, A., Barraja, P., Tesoriere, L., Cirrincione, G., Diana, P., and Parrino, B., Mar. Drugs, 2016, vol. 14, pp. 226–244.

    Article  CAS  PubMed Central  Google Scholar 

  43. Das, D., Banerjee, R., and Mitra, A., J. Chem. Pharm. Res., 2014, vol. 6, no. 11, pp. 108–116.

    Google Scholar 

  44. Silva, M.S., Pinto, D.C.G.A., Cavaleiro, J.A.S., Levai, A., and Patonay, T., Arkivoc, 2004, vol. VII, pp. 106–123.

    Google Scholar 

  45. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Bokesch, H., Kenney, S., and Boyd, M.R., J. Nati. Cancer Inst., 1990, vol. 82, pp. 1107–1112.

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

Authors would like to express their deep appreciation and indebtedness to Chemistry Department, Faculty of Science, Ain Shams University, for their support of the work.

Author information

Authors and Affiliations

Authors

Ethics declarations

The authors declare that they have no conflict of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.

Additional information

The article is published in the original.

Corresponding author: e-mail: marwa_k@sci.asu.edu.eg.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Eman A. El-Helw, Derbala, H.A., El-Shahawi, M.M. et al. Synthesis and In Vitro Antitumor Activity of Novel Chromenones Bearing Benzothiazole Moiety. Russ J Bioorg Chem 45, 42–53 (2019). https://doi.org/10.1134/S1068162019010047

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162019010047

Keywords:

Navigation