Issue

Vol. 27 No. 4 (2015): Vol 27 Issue 4

Copyright (c) 2015 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Design and Synthesis of Novel Aspirin-Caffeic Acid Ester Hybrids for Cardioprotection with Reduced Risk of Hemorrhagic Stroke

https://doi.org/10.14233/ajchem.2015.17896
Zhi-Hao Shi
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China; Department of Organic Chemistry, China Pharmaceutical University, Nanjing, P.R. China
Nian-Guang Li
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China
Yu-Ping Tang
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China
Qian-Ping Shi
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China
Wei Zhang
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China
Peng-Xuan Zhang
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China
Ze-Xi Dong
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China
Wei Li
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China
Jin-Ao Duan
National and Local Collaborative Engeering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, P.R. China

Corresponding Author(s) : Nian-Guang Li

linianguang@njutcm.edu.cn

Asian Journal of Chemistry, Vol. 27 No. 4 (2015): Vol 27 Issue 4

Abstract

A series of novel aspirin-caffeic acid ester hybrids for cardioprotection with reduced risk of hemorrhagic stroke were designed and synthesized by coupling aspirin and caffeic acid esters inspired by NCX-4016. The synthesized compounds were evaluated for their in vitro antiplatelet aggregations induced by ADP and antioxidant activity of the caffeic acid esters which could be released from the hybrids by esterases in vivo like NCX 4016 were determined by DPPH assay. The results showed that compound 3d exhibited potent antiplatelet activity than aspirin and its intermediate caffeic acid isopropyl ester (2d) showed good antioxidant activity and thus could be considered to be novel potent cardioprotectic drug candidates with reduced risk of hemorrhagic stroke.

Keywords

Hemorrhagic stroke Aspirin Caffeic acid Synthesis
Shi, Z.-H., Li, N.-G., Tang, Y.-P., Shi, Q.-P., Zhang, W., Zhang, P.-X., … Duan, J.-A. (2015). Design and Synthesis of Novel Aspirin-Caffeic Acid Ester Hybrids for Cardioprotection with Reduced Risk of Hemorrhagic Stroke. Asian Journal of Chemistry, 27(4), 1342–1346. https://doi.org/10.14233/ajchem.2015.17896
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. Antithrombotic Trialists’ Collaboration, BMJ, 328, 71 (2002); doi:10.1136/bmj.324.7329.71.
  2. K. Schrör, Drugs, 50, 7 (1995); doi:10.2165/00003495-199550010-00002.
  3. P.J. Loll, D. Picot and R.M. Garavito, Nat. Struct. Biol., 2, 637 (1995); doi:10.1038/nsb0895-637.
  4. M.M. Wolfe, D.R. Lichtenstein and G. Singh, N. Engl. J. Med., 340, 1888 (1999); doi:10.1056/NEJM199906173402407.
  5. J.R. Vane and R.M. Botting, Inflamm. Res., 47, 78 (1998); doi:10.1007/s000110050284.
  6. L. Ma, P. del Soldato and J.L. Wallace, Proc. Natl. Acad. Sci. USA, 99, 13243 (2002); doi:10.1073/pnas.202392199.
  7. W.W. Zuurmond, Clin. Rheumatol., 20(S1), 6 (2001); doi:10.1007/BF03342661.
  8. J.L. Wallace, L.J. Ignarro and S. Fiorucci, Nat. Rev. Drug Discov., 1, 375 (2002); doi:10.1038/nrd794.
  9. D. Steinberg, S. Parthasarathy, T.E. Carew, J.C. Khoo and J.L. Witztum, N. Engl. J. Med., 320, 64 (1989); doi:10.1056/NEJM198901053200122.
  10. C. Napoli, F. de Nigris, S. Williams-Ignarro, O. Pignalosa, V. Sica and L.J. Ignarro, Nitric Oxide, 15, 265 (2006); doi:10.1016/j.niox.2006.03.011.
  11. J.F. Keaney Jr. and J.A. Vita, Prog. Cardiovasc. Dis., 38, 129 (1995); doi:10.1016/S0033-0620(05)80003-9.
  12. H. Ogita and J.K. Liao, Endothelium, 11, 123 (2004); doi:10.1080/10623320490482664.
  13. A. Cherubini, G.B. Vigna, G. Zuliani, C. Ruggiero, U. Senin and R. Fellin, Curr. Pharm. Des., 11, 2017 (2005); doi:10.2174/1381612054065783.
  14. D. Praticò, Atherosclerosis, 181, 215 (2005); doi:10.1016/j.atherosclerosis.2005.03.005.
  15. P. Mattila and J. Kumpulainen, J. Agric. Food Chem., 50, 3660 (2002); doi:10.1021/jf020028p.
  16. S. Bryngelsson, L.H. Dimberg and A. Kamal-Eldin, J. Agric. Food Chem., 50, 1890 (2002); doi:10.1021/jf011222z.
  17. M. Castellari, E. Sartini, A. Fabiani, G. Arfelli and A. Amati, J. Chromatogr. A, 973, 221 (2002); doi:10.1016/S0021-9673(02)01195-0.
  18. Y. Kono, K. Kobayashi, S. Tagawa, K. Adachi, A. Ueda, Y. Sawa and H. Shibata, Biochim. Biophys. Acta, 1335, 335 (1997); doi:10.1016/S0304-4165(96)00151-1.
  19. I. Gülçin, Toxicology, 217, 213 (2006); doi:10.1016/j.tox.2005.09.011.
  20. M. Nardini, M. D'Aquino, G. Tomassi, V. Gentili, M. Di-Felice and C. Scaccini, Free Radic. Biol. Med., 19, 541 (1995); doi:10.1016/0891-5849(95)00052-Y.
  21. H. Stamatis, V. Sereti and F.N. Kolisis, J. Mol. Catal. B, 11, 323 (2001); doi:10.1016/S1381-1177(00)00016-3.
  22. T. Nagaoka, A.H. Banskota, Y. Tezuka, I. Saiki and S. Kadota, Bioorg. Med. Chem., 10, 3351 (2002); doi:10.1016/S0968-0896(02)00138-4.
  23. F. de Campos Buzzi, C.L. Franzoi, G. Antonini, M. Fracasso, V.C. Filho, R.A. Yunes and R. Niero, Eur. J. Med. Chem., 44, 4596 (2009); doi:10.1016/j.ejmech.2009.06.029.
  24. B. Jayaprakasam, M. Vanisree, Y. Zhang, D.L. Dewitt and M.G. Nair, J. Agric. Food Chem., 54, 5375 (2006); doi:10.1021/jf060899p.
  25. D.Y. Yuk, C.K. Ryu, J.T. Hong, K.H. Chung, W.S. Kang, Y. Kim, H.S. Yoo, M.K. Lee, C.K. Lee and Y.P. Yun, Biochem. Pharmacol., 60, 1001 (2000); doi:10.1016/S0006-2952(00)00411-1.
  26. H. Wang, X.D. Gao, G.C. Zhou, L. Cai and W.B. Yao, Food Chem., 106, 888 (2008); doi:10.1016/j.foodchem.2007.05.068.
  27. G.A. Olah, T. Keumi and D. Meidar, Synthesis, 929 (1978); doi:10.1055/s-1978-24945.
  28. Y.Q. Li, Synth. Commun., 29, 3901 (1999); doi:10.1080/00397919908085911.
  29. G.S. Zhang, Synth. Commun., 29, 607 (1999); doi:10.1080/00397919908085809.
  30. C.O. Kappe, Angew. Chem. Int. Ed. Engl., 43, 6250 (2004); doi:10.1002/anie.200400655.
  31. N.G. Li, Z.H. Shi, Y.P. Tang, B.Q. Li and J.A. Duan, Molecules, 14, 2118 (2009); doi:10.3390/molecules14062118.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0