Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis and Antiproliferative Potency within Anticonvulsant of Novel Bichalcone Derivatives

  • Mansour, Eman (Organic Chemistry Dep., Faculty of Women's for Arts, Science and Education, Ain Shams University) ;
  • El-Badry, Yaser A. (Organic Chemistry Lab., Faculty of Specific Education, Ain Shams University) ;
  • El-Tokhy, Afaf (Organic Chemistry Dep., Faculty of Women's for Arts, Science and Education, Ain Shams University) ;
  • Ayyad, Rezed (Pharmaceutical Chemistry Department, Faculty of Pharmacy, Al-Azhar University) ;
  • Abd-Rabou, Ahmed A. (Hormones Department, Medical Research Division, National Research Centre)
  • Received : 2019.09.19
  • Accepted : 2019.11.18
  • Published : 2020.02.20
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Abstract

An efficient and facile procedure has been developed for the synthesis of novel bichalcone derivatives (4a, 4b). The key step contains the solvent-free aldol synthesis of bichalcones based on quinones. Bichalcones (4a, 4b) were used as precursors for the synthesis of some interesting heterocyclic compounds like, diazepines (5a, 5b), pyrazolo-pyrimidines (7a, 7b), and pyrazoline derivatives (8a, 8b). Moreover, new thioxopyrimidine derivatives (9a, 9b) were furnished and used as a functionalizing agent to produce the triazole-pyrimidines (11, 12) and the carbonitrile derivative (14). All the synthesized compounds were fully characterized using physical and spectral data like, FT-IR, 1H NMR, 13C NMR, and MS. Bichalcones (4a, 4b) and diazepines (5a, 5b) were screened for their anticonvulsant activity, where compounds (4a, 5a, and 5b) revealed potent anticonvulsant activity compared to diazepam. On the other hand, some of the prepared compounds were screened for their antiproliferative activity and they showed significant cytotoxic effects on most of the cancer cell lines with regard to broad spectrum antitumor activity.

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References

  1. El-Najjar, N.; Gali-Muhtasib, H.; Ketola, R. A.; Vuorela, P.; Urtti, A.; Vuorela, H. Phytochem. Rev. 2011, 10, 353. https://doi.org/10.1007/s11101-011-9209-1
  2. Nassar, E.; El-Farargy, A. F.; Abdelrazek, F. M. J. Heterocyclic Chem. 2015, 52, 1395. https://doi.org/10.1002/jhet.2246
  3. Zahran, M. A. H.; Salama, H. F.; Abdin, Y. G.; Gamal-Eldeen, A. M. J. Chem. Sci. 2010, 122, 587. https://doi.org/10.1007/s12039-010-0093-9
  4. Teng, Y.; Li, X.; Yang, K.; Li, X.; Zhang, Z.; Wang, L.; Deng, Z.; Song, B.; Yan, Z.; Zhang, Y.; Lu, K.; Yu, P. Eur. J. Med. Chem. 2017, 125, 335. https://doi.org/10.1016/j.ejmech.2016.09.024
  5. Nassar, E. J. Am. Sci. 2010, 6, 338.
  6. Asiri, A. M.; Khan, S. A. Molecules 2011, 16, 523. https://doi.org/10.3390/molecules16010523
  7. Kumar, D.; Kumar, N. M.; Akamatsu, K.; Kusaka, E.; Harada, H.; Ito, T. Bioorg. Med. Chem. Lett. 2010, 20, 3916. https://doi.org/10.1016/j.bmcl.2010.05.016
  8. Queiroz, M. R. P.; Abreu, A. S.; Carvalho, M. S. D.; Ferreira, P. M. T.; Nazareth, N.; Nascimento, M. S. Bioorg. Med. Chem. 2008, 16, 5584. https://doi.org/10.1016/j.bmc.2008.04.004
  9. Nassar, E.; Abdelrazek, F. M.; Ayyad, R. R.; El-Farargy, A. F. Mini-Rev. Med. Chem. 2016, 16, 926. https://doi.org/10.2174/1389557516666160118105505
  10. Pillai, A. D.; Rathod, P. D.; Patel, M.; Nivsarkar, M.; Vasu, K. K.; Padh, H.; Sudarsanam, V. Biochem. Biophys. Res. Commun. 2003, 301, 183. https://doi.org/10.1016/S0006-291X(02)02996-0
  11. Venkatachalam, S. R.; Salaskar, A.; Chattopadhyay, A.; Barik, A.; Mishra, B.; Gangabhagirathi, R.; Priyadarsini, K. I. Bioorg. Med. Chem. 2006, 14, 6414. https://doi.org/10.1016/j.bmc.2006.05.042
  12. Sowmya, P. T.; Rai, K. M. L. J. Chem. Sci. 2017, 129, 67. https://doi.org/10.1007/s12039-016-1205-y
  13. Kaur, N.; Kishore, D. J. Chem. Sci. 2013, 125, 555. https://doi.org/10.1007/s12039-013-0412-z
  14. Mihigo, S. O.; Mammo, W.; Bezabih, M.; Andrae-Marobela, K.; Abegaz, B. M. Bioorg. Med. Chem. 2010, 18, 2464. https://doi.org/10.1016/j.bmc.2010.02.055
  15. Katritzaky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry, 1st ed.; Pergamon Press: New York, 1984; p 108.
  16. Satyanarayana, M.; Tiwari, P.; Tripathi, B. K.; Srivastava, A. K.; Pratap, R. Bioorg. Med. Chem. 2004, 12, 883. https://doi.org/10.1016/j.bmc.2003.12.026
  17. Palleros, D. R. J. Chem. Educ. 2004, 81, 1345. https://doi.org/10.1021/ed081p1345
  18. Toda, F.; Tanaka, K.; Hamai, K. J. Chem. Soc. Perkin. Trans. 1 1990, 3207.
  19. Lipson, V. V.; Desenko, S. M.; Borodina, V. V.; Shirobokova, M. G. Chem. Heterocycl. Com. 2007, 43, 1544. https://doi.org/10.1007/s10593-007-0239-y
  20. Hussein, A. M.; Ishak, E. A.; Atalla, A. A.; Hafiz, S. A.; Elnagdi, M. H. Phosphorus Sulfur and Silicon and the Related Elements 2007, 182, 2897. https://doi.org/10.1080/10426500701542858
  21. Sayed, A. Z.; Aboul-Fetouh, M. S.; Nassar, H. S. J. Mol. Struct. 2012, 1010, 146. https://doi.org/10.1016/j.molstruc.2011.11.046
  22. Elnagdi, M. H.; Erian, A. W. Bull. Chem. Soc. Jpn. 1990, 63, 1854. https://doi.org/10.1246/bcsj.63.1854
  23. Nassar, E.; El-Badry, Y. A.; Eltoukhy, A. M. M.; Ayyad, R. R. Med. Chem. 2016, 6, 224. https://doi.org/10.4172/2161-0444.1000350
  24. Flefel, E. E.; Salama, M. A.; El-Shahat, M.; El-Hashash, M. A.; El-Farargy, A. F. Phosphorus Sulfur and Silicon and the Related Elements 2007, 182, 1739. https://doi.org/10.1080/10426500701313912
  25. Raj, M. A.; Revin, S. B.; John, S. A. Bioelectrochemistry 2013, 89, 1. https://doi.org/10.1016/j.bioelechem.2012.08.003
  26. Nassar, E.; El-Badry, Y. A.; Kazaz, H. E. Chem. Pharm. Bull. 2016, 64, 558. https://doi.org/10.1248/cpb.c15-00922
  27. Devi, J. M.; Ali, K. S.; Venkatraman, V. R.; Ramakrishnan, S. K.; Ramachandran, K. A. A. Therochim. Acta 2005, 438, 29. https://doi.org/10.1016/j.tca.2005.08.009
  28. Ando, M.; Nishida, H.; Nishino, Y.; Ohbayashi, M.; Ueda, K.; Okamoto, Y.; Kojima, N. Toxicol. Lett. 2010, 199, 213. https://doi.org/10.1016/j.toxlet.2010.08.024
  29. Grever, M. R.; Schepartz, S. A.; Chabner, B. A. Semin. Oncol. 1992, 19, 622.
  30. Shoemaker, R. H. Nat. Rev. Cancer 2006, 6, 813. https://doi.org/10.1038/nrc1951
  31. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Langley, J.; Vaigro-Wolf, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd, M. J. Natl. Cancer I 1991, 83, 757. https://doi.org/10.1093/jnci/83.11.757
  32. Alley, M. C.; Scudiero, D. A.; Monks,P. A.; Hursey, M. L.; Czerwinski, M. J. Cancer Res. 1988, 48, 589.
  33. Boyd, M. R.; Paull, K. D. Drug Develop. Res. 1995, 34, 91. https://doi.org/10.1002/ddr.430340203