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Regioselective synthesis and evaluation of novel sulfonamide 1,2,3-triazole derivatives as antitumor agents

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Abstract

A novel series of 1,2,3-triazole containing sulfonamide moiety was synthesized. Treatment of 4-acetyl 1,2,3-triazole 3 with different aldehydes gave α,β-unsaturated ketones 4a–c. Condensation of 3 with dimethylformamide dimethylacetal (DMF-DMA) gave formimidamide 5. Chalcone 7 was achieved via two ways from the reaction of 5 with benzaldehyde or from treatment of 4a with DMF-DMA. Reaction of 7 with hydrazine hydrate afforded pyrazoline 8. 5-Methyl pyrazole 12 was synthesized from Claisen condensation reaction of 3 or 5 with ethyl acetate to give 1,3-diketone adduct 9 or 10, respectively, followed by treatment with hydrazine hydrate. 5-Aminopyrazole 17 was synthesized from the reaction of ester 13 or formimidamide ester 13a with acetonitrile to afford cyanoacetyl derivatives 14 or 15, respectively, followed by treatment with hydrazine hydrate. The new compounds were screened for their in vitro antitumor activity. The results of this investigation revealed that compounds 12, 7, and 17 had a significant anticancer activity against MCF-7 cancer cell line with IC50 values 12.4, 19.8, and 23.4 µM, respectively, in relation to the standard drug, doxorubicin.

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References

  1. O.A. Fathalla, S.M. Awad, M.S. Mohamed, Arch. Pharm. Res. 28(11), 1205–1212 (2005)

    Article  CAS  PubMed  Google Scholar 

  2. E. Willsteed, M. Lee, L.C. Wong, A. Cooper, Aust. J. Dermat. 46(2), 101–103 (2005)

    Article  Google Scholar 

  3. C. Hansch, P.G. Sammes, J.B. Taylor, Comprehensive medicinal chemistry, vol. 2 (Pergamon Press, Oxford, 1990)

    Google Scholar 

  4. T. Ana, N. Vesna, N. Ljubiša, S. Ivan, Adv. Technol. 6(1), 58–71 (2017)

    Article  Google Scholar 

  5. S.S. Stokes, R. Albert, EdT Buurman, B. Andrews, A.B. Shapiro, O.M. Green, A.R. McKenzie, L.R. Otterbein, Bioorg. Med. Chem. Lett. 22, 7019–7023 (2012)

    Article  CAS  PubMed  Google Scholar 

  6. J.J. Li, D. Anderson, E.G. Burton, J.N. Cogburn, J.T. Collins, D.J. Garland, S.A. Gregory, H.C. Huang, P.C. Isakson, C.M. Koboldt, E.W. Logusch, M.B. Norton, W.E. Perkins, E.J. Reinhard, K. Seibert, A.W. Veenhuizem, Y. Zang, D.B. Reitz, J. Med. Chem. 38(22), 4570–4578 (1995)

    Article  CAS  PubMed  Google Scholar 

  7. K. Chibale, H.H. Kendrick, K.V. Yardley, A. Saravanamuthu, A.H. Fairlamb, S.L. Croft, Bioorg. Med. Chem. Lett. 11, 2655–2657 (2001)

    Article  CAS  PubMed  Google Scholar 

  8. Y. Kanda, Y. Kawanishi, K. Oda, T. Sakata, S. Mihara, K. Asakura, T. Kanemasa, M. Ninomiya, M. Fujimoto, T. Kanoike, Bioorg. Med. Chem. 9, 897–907 (2001)

    Article  CAS  PubMed  Google Scholar 

  9. A. Natarajan, Y. Guo, F. Harbinski, Y.-H. Fan, H. Chen, L. Luus, J. Diercks, H. Aktas, M. Chorev, J.A. Halperin, J. Med. Chem. 47, 4979–4982 (2004)

    Article  CAS  PubMed  Google Scholar 

  10. G.C. Serradeil-Le, Cardiovasc. Drug. Rev. 19, 201–2014 (2001)

    Google Scholar 

  11. D. Vullo, V. De Luca, A. Scozzafava, V. Carginale, M. Rossi, C.T. Supuran, C. Capasso, Bioorg. Med. Chem. Lett. 24, 275–279 (2014)

    Article  CAS  PubMed  Google Scholar 

  12. A. Kołaczek, I. Fusiarz, J. Ławecka, D. Branowska, CHEMIK 68(7), 620–628 (2014)

    Google Scholar 

  13. D.-K. Kim, J.Y. Lee, N. Lee, D.H. Ryu, J.-S. Kim, S. Lee, J.-Y. Choi, J.-H. Ryu, N.-H. Kim, G.-J. Im, W.-S. Choi, T.-K. Kim, Bioorg. Med. Chem. 9, 3013–3021 (2001)

    Article  CAS  PubMed  Google Scholar 

  14. J.I. Levin, J.M. Chen, M.T. Du, F.C. Nelson, L.M. Killar, S. Skala, A. Sung, G. Jin, R. Cowling, D. Barone, C.J. March, K.M. Mohler, R.A. Black, J.S. Skotnicki, Bioorg. Med. Chem. Lett. 12, 1199–1202 (2002)

    Article  CAS  PubMed  Google Scholar 

  15. B. Hu, J. Ellingboe, S. Han, E. Largis, K. Lim, M. Malamas, R. Mulvey, C. Niu, A. Oliphant, J. Pelletier, T. Singanallore, F.-W. Sum, J. Tillett, V. Wong, Bioorg. Med. Chem. 8, 2045–2059 (2001)

    Article  Google Scholar 

  16. L.-Y. Ma, B. Wang, L.-P. Pang, M. Zhang, S.-Q. Wang, Y.-C. Zheng, K.-P. Shao, D.-Q. Xue, H.-M. Liu, Bioorg. Med. Chem. 25, 1124–1128 (2015)

    Article  CAS  Google Scholar 

  17. M. Dekker, in Protease Inhibitors in AIDS Therapy, ed. by R.C. Ogden, C.W. Flexner (Basel, New York, NY, 2001)

  18. X.-L. Wang, K. Wan, C.-H. Zhou, Eur. J. Med. Chem. 45, 4631–4639 (2010)

    Article  CAS  PubMed  Google Scholar 

  19. A. Rajasekaran, S. Murugesan, K. AnandaRajagopal, Arch. Pharm. Res. 29, 535–554 (2006)

    Article  CAS  PubMed  Google Scholar 

  20. D. Gupta, D.K.J. Jain, J. Adv. Pharm. Technol. Res. 6, 141–146 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. R. Paprocka, M. Wiese, A. Eljaszewicz, A. Helmin-Basa, A. Gzella, B. Modzelewska-Banachiewicz, J. Michalkiewicz, Bioorg. Med. Chem. Lett. 25, 2664–2667 (2015)

    Article  CAS  PubMed  Google Scholar 

  22. M. Jarrahpour, M. Aye, J.A. Rad et al., J. Iran. Chem. Soc. 15, 1311–1326 (2018)

    Article  CAS  Google Scholar 

  23. Y.-W. He, C.-Z. Dong, J.-Y. Zhao, L.-L. Ma, Y.-H. Li, H.A. Aisa, Eur. J. Med. Chem. 76, 245–255 (2014)

    Article  CAS  PubMed  Google Scholar 

  24. R. Kharb, M.S. Yar, P.C. Sharma, Mini. Rev. Med. Chem. 11, 84–96 (2011)

    Article  CAS  PubMed  Google Scholar 

  25. R. Bollu, J. Devi Palem, R. Bantu, V. Guguloth, L. Nagarapu, S. Polepalli, N. Jain, Eur. J. Med. Chem. 89, 138–146 (2015)

    Article  CAS  PubMed  Google Scholar 

  26. D.-J. Fu, Y.-C. Liu, J.-J. Yang, J. Zhang, C.-D. Xiong, Z.-S. Cao, X.-X. Yin, W. Wei, Y.-B. Zhang, J. Chem. Res. 41(9), 523–525 (2017)

    Article  CAS  Google Scholar 

  27. L. Vats, V. Sharma, A. Angeli, R. Kumar, T.C. Supuran, K. Sharma, Eur. J. Med. Chem. 150, 678–686 (2018)

    Article  CAS  PubMed  Google Scholar 

  28. S.-J. Yan, Y.-J. Liu, Y.-L. Chen, L. Liu, J. Lin, Bioorg. Med. Chem. Lett. 20(17), 5225–5228 (2010)

    Article  CAS  PubMed  Google Scholar 

  29. T. Ma, A.D. Fuld, J.R. Rigas, A.E. Hagey, G.B. Gordon, E. Dmitrovsky, K.H. Dragnev, Chemotherapy 58, 321–329 (2012)

    Article  CAS  PubMed  Google Scholar 

  30. A.A. Abd-Rabou, B.F. Abdel-Wahab, M.S. Bekheit, Chem. Pap. 72, 2225–2237 (2018)

    Article  CAS  Google Scholar 

  31. R.E. Khidre, S.R. El-Gogary, M.S. Mostafa, J. Heterocycl. Chem. 54, 2511–2519 (2017)

    Article  CAS  Google Scholar 

  32. R.E. Khidre, B.F. Abdel-Wahab, G.E.A. Awad, Heterocycles 94, 314–325 (2017)

    Article  CAS  Google Scholar 

  33. R.E. Khidre, I.M. Rodini, D.A. Ibrahim, ARKIVOC 5, 301–317 (2016)

    Google Scholar 

  34. I.A.M. Radini, R.E. Khidre, E.M. El-Telbani, Lett. Drug. Design. Discov. 13, 921–931 (2016)

    Article  CAS  Google Scholar 

  35. I.A.M. Radini, T.M.Y. Elsheikh, E.M. El-Telbani, R.E. Khidre, Molecules 21, 909 (2016)

    Article  CAS  PubMed Central  Google Scholar 

  36. E.M. El-Telbani, N.M.A. El-Ebiary, R.H. Swellem, I.F. Zeid, G.A.M. Nawwar, Lett. Drug. Design. Discov. 10(5), 444–452 (2013)

    Article  Google Scholar 

  37. F. El Shehry, A.A. Abu-Hashem, E.M. El-Telbani, Eur. J. Med. Chem. 45, 1906–1911 (2010)

    Article  CAS  PubMed  Google Scholar 

  38. R. Kumar, V. Sharma, S. Bua, C.T. Supuran, P.K. Sharma, J. Enzym. Inhib. Med. Chem. 32, 1187–1194 (2017)

    Article  CAS  Google Scholar 

  39. S. Mackay, C.J. Gilmore, C. Edwards, N. Stewart, K. Shankland, maXus computer program for the solution and refinement of crystal structures (Japan & The University of Glasgow, Bruker Nonius, 1999)

    Google Scholar 

  40. B.R. Brooks, C.L. Brooks, A.D. Mackerell, L. Nilsson, R.J. Petrella, B. Roux, Y. Won, G. Archontis, C. Bartels, S. Boresch, A. Caflisch, L. Caves, Q. Cui, A.R. Dinner, M. Feig, S. Fischer, J. Gao, M. Hodoscek, W. Im, K. Kuczera, T. Lazaridis, J. Ma, V. Ovchinnikov, E. Paci, R.W. Pastor, C.B. Post, J.Z. Pu, M. Schaefer, B. Tidor, R.M. Venable, H.L. Woodcock, X. Wu, W. Yang, D.M. York, M. Karplus, J. Comp. Chem. 30, 1545–1615 (2009)

    Article  CAS  Google Scholar 

  41. F.A. Momany, R. Rone, J. Comp. Chem. 13, 888–900 (1992)

    Article  CAS  Google Scholar 

  42. G. Wu, D.H. Robertson, C.L. Brooks III, M. Vieth, J. Comp. Chem. 24, 1549–1562 (2003)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors like to thank Dr. Aly Fahmy, Vacsera, Cairo, Egypt, for handling the antitumor properties.

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Authors and Affiliations

  1. Chemical Industries Division, National Research Centre, Dokki, Giza, 12622, Egypt

    Rizk E. Khidre & Emad M. El-Telbani

  2. Chemistry Department, Faculty of Science, Jazan University, Jazan, 2079, Saudi Arabia

    Sameh R. Elgogary, Rizk E. Khidre & Emad M. El-Telbani

  3. Chemistry Department, Faculty of Science, Damietta University, Damietta, Egypt

    Sameh R. Elgogary

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  1. Sameh R. Elgogary
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Correspondence to Rizk E. Khidre or Emad M. El-Telbani.

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Elgogary, S.R., Khidre, R.E. & El-Telbani, E.M. Regioselective synthesis and evaluation of novel sulfonamide 1,2,3-triazole derivatives as antitumor agents. J IRAN CHEM SOC 17, 765–776 (2020). https://doi.org/10.1007/s13738-019-01796-y

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