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SYNTHESIS, CRYSTAL STRUCTURE, AND BIOLOGICAL EVALUATION OF (E)-1-(4-(4-BROMOBENZYL)PIPERAZIN-1-YL)- 3-(4-CHLOROPHENYL)PROP-2-EN-1-ONE

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Abstract

Title compound (E)-1-(4-(4-bromobenzyl)piperazin-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one (5) (C20H20BrClN2O, Mr = 419.74) is designed, synthesized, and evaluated for its biological activity. Its structure is confirmed by FTIR, 1H and 13C NMR, HRMS, and X-ray single crystal diffraction. The structure is stabilized via inter- as well as intra- C–H…O interactions and intra hydrogen bonding C–H…N interactions. The Hirshfeld surface intermolecular interactions are studied using the crystal structure. The maximum surface area of the molecule is occupied by C–H…O interactions. In addition, the biological activity in vitro and in vivo of title compound 5 is also evaluated.

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REFERENCES

  1. R. W. V. Flynn, R. S. M. MacWalter, and A. S. F. Doney. Neuropharmacology, 2008, 55, 250–256.

  2. J. D. Pandian, V. Padma, P. Vijaya, P. N. Sylaja, and J. M. K. Murthy. Int. J. Stroke, 2007, 2, 17–26.

  3. D. W. Choi. Neuron, 1988, 1, 623–634.

  4. C. Lv, X. Yuan, H. W. Zeng, R. H. Liu, and W. D. Zhang. Eur. J. Pharmacol., 2017, 815, 487–494.

  5. K. Uchino. JAMA Neurol., 2017, 74, 1269.

  6. N. R. Mohan, S. Sreenivasa, K. E. Manojkumar, T. M. C. Rao, B. S. Thippeswamy, and P. A. Suchetan. J. Braz. Chem. Soc., 2014, 25, 1012–1020.

  7. M. Han, Y. Han, C. Song, and H. G. Hahn. Bull. Korean Chem. Soc., 2012, 33, 2597–2602.

  8. L. L. Gan, J. L. Cai, and C. H. Zhou. Chin. Pharm. J., 2009, 44, 1361–1368.

  9. L. L. Gan, Y. H. Lu, and C. H. Zhou. Chin. J. Biochem. Pharm., 2009, 30, 127–131.

  10. V. R. Solomon, C. Hu, and H. Lee. Bioorg. Med. Chem., 2010, 18, 1563–1572.

  11. M. Kimura, T. Masuda, K. Yamada, N. Kawakatsu, N. Kubota, M. Mitani, K. Kishii, M. Inazu, Y. Kiuchi, K. Oguchi, and T. Namiki. Bioorg. Med. Chem. Lett., 2004, 14, 4287–4290.

  12. L. A. Shapiro, S. J. Offord, and G. A. Ordway. Brain Res., 1995, 677, 250–260.

  13. C. Yang, G. Xu, J. Li, X. Wu, B. Liu, X. Yan, M. Wang, and Y. Xie. Bioorg. Med. Chem. Lett., 2005, 15, 1505–1507.

  14. B. Qin, M. Nagasaki, M. Ren, G. Bajotto, Y. Oshida, and Y. Sato. Diabetes Res. Clin. Pract., 2003, 62, 139–148.

  15. D. M. Cheng, P. Kuhn, A. Poulev, L. E. Rojo, M. A. Lila, and I. Raskin. Food Chem., 2012, 135, 2994–3002.

  16. D. Fancelli, A. Abate, R. Amici, P. Bernardi, M. Ballarini, A. Cappa, G. Carenzi, A. Colombo, C. Contursi, F. D. Lisa, G. Dondio, S. Gagliardi, E. Milanesi, S. Minucci, G. Pain, P. G. Pelicci, A. Saccani, M. Storto, F. Thaler, M. Varasi, M. Villa, and S. Plyte. J. Med. Chem., 2014, 57, 5333–5347.

  17. G. M. Sheldrick. SHELXS-97, SHELXL-97 and SADABS, Version 2.05. University of Göttingen: Göttingen, Germany, 1997.

  18. F. L. Hirshfeld. Theor. Chim. Acta, 1977, 44, 129–138.

  19. J. J. McKinnon, A. S. Mitchell, and M. A. Spackman. Chem. Eur. J., 1998, 4, 2136–2141.

  20. S. K. Wolff, D. J. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, M. A. Spackman. CrystalExplorer, Version 3.1. University of Western Australia: Perth, Australia, 2012.

  21. M. A. Spackman and D. Jayatilaka. CrystEngComm, 2009, 11, 19–32.

  22. M. A. Spackman and J. J. McKinnon. CrystEngComm, 2002, 4, 378–392.

  23. A. Akaike, Y. Tamura, Y. Sato, and T. Yokota. Eur. J. Pharmacol., 1993, 241, 1–6.

  24. S. W. Ma, H. X. Liu, H. Y. Jiao, L. Y. Wang, L. Y. Chen, J. Liang, M. Zhao, and X. T. Zhang. NeuroToxicology, 2012, 33, 59–69.

  25. T. Mosmann. J. Immunol. Methods, 1983, 65, 55–63.

  26. T. Terauchi, T. Doko, M. Yonaga, A. Kajiwara, T. Niidome, R. Taguchi, T. Kume, A. Akaike, and H. Sugimoto. Bioorg. Med. Chem. Lett., 2006, 16, 5080–5083.

  27. Y. Y. Zhang, X. Y. Wang, X. R. Wang, Z. H. Xu, Z. Liu, Q. Ni, X. P. Chu, M. F. Qiu, A. H. Zhao, and W. Jia. J. Ethnopharmacol., 2006, 108, 355–360.

  28. R. Rodolfo, R. R. Isela, L. S. Darwin, V. Horacio, H. Enrique, M. Martha, and H. Ismael. J. Stroke Cerebrovasc. Dis., 2000, 9, 45–53.

  29. M. Li, L. R. Wen, W. J. Fu, F. Z. Hu, and H. Z. Yang. Chin. J. Struct. Chem., 2004, 23, 11–14.

  30. K. S. Saikat. CrystEngComm, 2013, 15, 1772–1781.

  31. K. S. Saikat. J. Mol. Struct., 2014, 1064, 70–75.

  32. K. Ohnuma, Y. Hayashi, M. Furue, K. Kaneko, and M. Asashima. J. Neurosci. Methods, 2006, 151, 250–261.

  33. H. R. Wang, B. Shao, H. Y. Yu, F. B. Xu, P. Y. Wang, K. Y. Yu, Y. F. Han, M. Song, Y F. Li, and Z. Cao. Chem. Biol. Interact., 2019, 299, 15–26.

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Funding

This research was supported by the Natural Science Foundation of China Grant (81371451) and the Natural Science Foundation of Jiangsu Province Grant (BK20131390).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing, People’s Republic of China

    L. -Y. Chen & Y. Zhong

  2. School of Pharmacy, Nanjing Medical University, Nanjing, People’s Republic of China

    C. -Z. Yang, Y. Xu & B. Wu

  3. Animal Core Facility of Nanjing Medical University, Nanjing, People’s Republic of China

    C. -Y. Qi

Authors
  1. L. -Y. Chen
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  2. C. -Z. Yang
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  3. Y. Xu
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  4. C. -Y. Qi
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  5. Y. Zhong
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  6. B. Wu
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Correspondence to Y. Zhong or B. Wu.

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Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 3, pp. 511-520.https://doi.org/10.26902/JSC_id69939

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Chen, L.Y., Yang, C.Z., Xu, Y. et al. SYNTHESIS, CRYSTAL STRUCTURE, AND BIOLOGICAL EVALUATION OF (E)-1-(4-(4-BROMOBENZYL)PIPERAZIN-1-YL)- 3-(4-CHLOROPHENYL)PROP-2-EN-1-ONE. J Struct Chem 62, 481–490 (2021). https://doi.org/10.1134/S002247662103015X

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  • DOI: https://doi.org/10.1134/S002247662103015X

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