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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 08: 1674 - 1685

DOI: https://doi.org/10.6023/cjoc201212050

Reviews

Synthesis Research Progress of Rofecoxib and Its Derivatives

  • Liu Gaizhi ,
  • Han Deen ,
  • Wang Peng ,
  • Liu Hongmin
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  • a Henan University of TCM, Zhengzhou 450046;
    b School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001

Received date: 2012-12-30

  Revised date: 2013-02-05

  Online published: 2013-02-22

Supported by

Project supported by the Doctoral Research Foundation of Henan University of Traditional Chinese Medicine (No. BSJJ2010-03).

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Abstract

Rofecoxib is a novel non-steroidal anti-inflammatory drug, which is the representative of cyclooxygenase inhibitor. Taking rofecoxib would increase the risk of heart attack or stroke risk. Although rofecoxib withdrawal from the market due to cardiovascular risk, but its excellent analgesic and anti-inflammatory activity still has great research value and broad application prospect. Therefore, rofecoxib as a lead compound, has become a focus of research, from which researchers try to find good activity and little side effects rofecoxib derivatives. The research progress of rofecoxib and its derivatives is reviewed, including synthesis of rofecoxib and its derivatives.

Key words： rofecoxib; derivative; synthesis; research progress

Cite this article

Liu Gaizhi , Han Deen , Wang Peng , Liu Hongmin . Synthesis Research Progress of Rofecoxib and Its Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1674 -1685 . DOI: 10.6023/cjoc201212050

References

[1] Wang, R.-Y. Chin. J. New Drugs 2000, 9, 661 (in Chinese).
(王仁云, 中国新药杂志, 2000, 9, 661.)
[2] Scott, L. J.; Lamb, H. M. Drugs 1999, 58, 499.
[3] Ehrich, E. W.; Dallob, A.; Lepeleire, I. D.; Hecken, A. V.; Riendeau, D.; Yuan, W.; Porras, A.; Wittreich, J.; Seibold, J. R.; Schepper, P. D.; Mehlisch, D. R.; Gertz, B. J. Clin. Pharmacol. Ther. 1999, 65, 336.
[4] Hawkey, C. J. Lancet 1999, 353, 307.
[5] Hecken, A. V.; Depré, M.; Ehrich, E.; Lepeleire, I. D.; Hilliard, D.; Porras, A.; Wong, P.; Buntinx, A.; Gertz, B. J.; Schepper, P. J. D. Clin. Pharmacol. Ther. 1999, 65, 164.
[6] Morrison, B. W.; Daniels, S. E.; Kotey, P. Obstet. Gynecol. 1999, 94, 504.
[7] Zhang, W. China Pharmacist 2005, 8, 474 (in Chinese).
(张伟, 中国药师, 2005, 8, 474.)
[8] Shrn, J; Li, B.-B. Evaluation Anal. Drug 2006, 6, 69 (in Chinese).
(沈娟, 李彬彬, 中国医院用药评价与分析, 2006, 6, 69.)
[9] Ma, Y.-Z.; Liu, Y.-X.; Zhou, Y.-P.; Mei, W.-J.; She, Z.-G. J. Guandong College Pharm. 2005, 21, 649 (in Chinese).
(马玉卓, 刘鹰翔, 周玉平, 梅文杰, 佘志刚, 广东药学院学报, 2005, 21, 649.)
[10] Desmond, R.; Dolling, U.; Marcune, B.; Tillyer, R.; Tschaen, D. WO 9608482, 1996 [Chem. Abstr. 1996, 125, 86474].
[11] Atkinson, J. G., Wang, Z.-Y. WO 9613483, 1996 [Chem. Abstr. 1996, 125, 114294].
[12] Desmond, R.; Dolling, U. H.; Frey, L. F.; Tillyer, R.; Tschaen, D. M. WO 9800416, 1996[Chem. Abstr. 1996, 128, 114869].
[13] Michel, T.; Jacques, Y. G.; Yves, L.; Serge, L.; Hélène, P.; Petpiboon, P.; Wang, Z.-Y. Synthesis 2001, 1778.
[14] Ao, G. Z.; Wang, W. D.; Zhang, Y. H. Chin. J. Pharm. 2002, 6, 267 (in Chinese).
(敖桂珍, 王未东, 张奕华, 中国医药工业杂志, 2002, 6, 267.)
[15] Gans, K. R.; Galbrainth, W.; Roman, R. J.; Haber, S. B.; Kerr, J. S.; Schmidt, W. K.; Smith, C.; Hewes, W. E.; Ackerman, N. R. J Pharmacol. Exp. Ther. 1990, 254, 180.
[16] Magolda, R. L.; Batt, D.; Covington, M. B. Inflamm. Res. 1995, 44 (suppl. 3), A274.
[17] Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J.S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins,W.E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347.
[18] Reitz, D. B.; Li, J. J.; Norton, M. B.; Reinhard, E. J.; Collins, J. T.; Anderson, G. D.; Gregory, S. A.; Koboldt, C. M.; Perkins,W. E. J. Med. Chem. 1994, 37, 3878.
[19] Vane, J. R.; Botting, R. M. Inflamm. Res. 1995, 44, 1.
[20] Chan, C. C.; Boyce, S.; Brideau, C.; Charleson, S.; Cromlish, W.; Ethier, D.; Evans, J.; Ford-Hutchinson, A. W.; Forrest, M. J.; Gauthier, J. Y.; Gordon, R.; Gresser, M.; Guay, J.; Kargman, S.; Kennedy, B.; Leblanc, Y.; Leger, S.; Mancini, J.; O'Neill, G. P.; Ouellet, M.; Patrick, D.; Percival, M. D.; Perrier, H.; Prasit, P.; Rodger, I. J. Pharmacol. Exp. Ther. 1999, 290, 551.
[21] Tacconelli, S.; Capone, M. L.; Sciulli, M. G.; Ricciotti, E.; Patrignani, P. Curr. Med. Res. Opin. 2002, 18, 503.
[22] Katz, J.; Fry, D.; Kehlet, H. 22nd Annual Scientific Meeting of the American Pain Society, Chicag, 2003, pp. 88～89.
[23] Su, X.-Y.; Wang, E.-H. Prog. Pharmacel. Sci. 2004, 28, 309 (in Chinese).
(苏晓岳, 王尔华, 药学进展, 2004, 28, 309.)
[24] Zhao, L.-Q.; Zhang, S.-F. Chin. J. Med. Chem. 1999, 9, 138 (in Chinese).
(赵丽琴, 张守芳, 中国药物化学杂志, 1999, 9, 138.)
[25] Saeed, E.; Alireza, F. Chin. J. Chem. 2006, 24, 791.
[26] Engelhardt, F. C.; Shi, Y.-J.; Cowden, C. J.; Conlon, D. A.; Pipik, B.; Zhou, G.; McNamara, J. M.; Dolling. U. J. Org. Chem. 2006, 71, 480.
[27] Ao, G.-Z.; Zhang, Y.-H.; Ji, H.; Deng, G.; Wu, Y.-J.; Peng, S.-X. J. China Pharm. Univ. 2002, 33, 460 (in Chinese).
(敖桂珍, 张奕华, 季晖, 邓钢, 吴艳俊, 彭司勋, 中国药科大学学报, 2002, 33, 460.)
[28] Wang, F.-Y.; Li, S.-L.; Feng, W.-L. J. Beijing Univ. Chem. Technol. 2004, 31, 84 (in Chinese).
(汪凤颖, 李顺来, 冯文林, 北京化工大学学报, 2004, 31, 84).
[29] Pan, H.-G.; Yu, X.-H.; Wu, D.-J. Synth. Chem. 2001, 9, 265 (in Chinese).
(潘海港, 虞鑫红, 吴达俊, 合成化学, 2001, 9, 265.)
[30] Liu, K. M.S. Thesis, Hebei Medical University, Shijiazhuang, 2003 (in Chinese).
(刘琨, 硕士论文, 河北医科大学, 石家庄, 2003.)
[31] Habeeb, A. G.; Praveen Rao, P. N.; Knaus, E. E. J. Med. Chem. 2001, 44, 3039.
[32] Navidpour, L.; Amini, M.; Shafaroodi, H.; Abdi, k.; Ghahremani, M. H.; Dehpour, A. R.; Shafiee, A. Bioorg. Med. Chem. Lett. 2006, 16, 4483.
[33] Zarghi, A.; Praveen Rao P. N.; Knaus, E. E. Bioorg. Med. Chem. 2007, 15, 1056.
[34] Chen, Q.-H.; Praveen, Rao P. N. Knaus, E. E. Bioorg. Med. Chem. 2006, 14, 7898.
[35] Caturla, F.; Amat, M.; Reinoso, R. F.; Cordoba, M.; Warrellow, G. Bioorg. Med. Chem. Lett. 2006, 16, 3209.
[36] Smith, N. D.; Reger, T. S.; Payne, J.; Zunic, J.; Lorrain, D.; Correa, L.; Stock, N.; Cramer, M.; Chen, W.-C.; Yang, J.; Prasit, P.; Munoz, B. Bioorg. Med. Chem. Lett. 2005, 15, 3197.
[37] Black, W. C.; Brideau, C.; Chan, C.-C.; Charleson, S.; Cromlish, W.; Gordon, R.; Grimm, E. L.; Hughes, G.; Leger, S.; Li, C.-S.; Riendeau, D.; Therien, M.; Wang, Z.-Y.; Xu, L.-J.; Prasit, P. Bioorg. Med. Chem. Lett. 2003, 13, 1195.
[38] Zarghi, A.; Praveen Rao P. N.; Knaus, E. E. Bioorg. Med. Chem. Lett. 2004, 14, 1957.
[39] Weber, V.; Rubat, C.; Duroux, E.; Lartigue, C.; Michel, M.; Pascal, C. Bioorg. Med. Chem. 2005, 13, 4552.
[40] Nicoll-Grith, D. A.; Yergey, J. A.; Trimble, L. A.; Silva, J. M.; Li, C.; Chauret, N.; Gauthier, J. Y.; Grimm, E.; Leger, S.; Roy, P.; Therien, M.; Wang, Z. Y.; Prasit, P.; Zamboni, R.; Young, R. N.; Brideau, C.; Chan, C.-C.; Mancini, J.; Riendeau, D. Bioorg. Med. Chem. Lett. 2000, 10, 2683.
[41] Desmond, R.; Dolling, U.; Marcune, B.; Tillyer, R.; Tschaen, D. WO 9608482, 1996 [Chem. Abstr. 1996, 125, 86474].
[42] Rowland, S. E.; Clark, P.; Gordon, R.; Mullen, A. K.; Guay, J.; Dufresne, L.; Brideau, C.; Cote, B.; Ducharme, Y.; Mancini, J.; Chan, C.-C.; Audoly, L.; Xu, D. Eur. J. Pharmacol. 2007, 560, 216.
[43] Dundar, Y.; Ünlü, S.; Banoglu, E.; Entrena, A.; Costantino, G.; Nuñez, M. T.; Ledo, F.; Sahin, M. F.; Noyanalpan, N. Eur. J. Med. Chem. 2009, 44,1830.
[44] Eren,G.; Ünlü, S.; Nuñez, M. T.; Labeaga,L.; Ledo, F.; Entrena, A.; Banoğlu, E.; Costantino, G.; Sahin. M. F. Bioorg. Med. Chem. 2010, 18, 6367.
[45] Abdellatif, K. R. A.; Huang, Z. J.; Chowdhury, M. A.; Kaufman, S.; Knaus, E.E. Bioorg. Med. Chem. Lett.2011, 21, 3951.
[46] Bhardwaj, A.; Kaur, J.; Sharma, S. K.; Huang, Z. J.; Wuest, F.; Knaus, E. E. Bioorg. Med. Chem. Lett. 2013, 23, 163
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