抗肿瘤活性双四氢异喹啉生物碱类似物的合成研究进展
收稿日期: 2018-10-30
修回日期: 2019-01-25
网络出版日期: 2019-03-29
基金资助
武汉工程大学科学研究基金(No.K201440)、湖北省教育厅科学研究计划指导性项目(No.B2016057)、新型反应器与绿色化学工艺湖北省重点实验室开放基金(No.201704)资助项目.
Progress in the Synthesis of Analogues of Bistetrahdro-isoquinoline Antitumor Alkaloids
Received date: 2018-10-30
Revised date: 2019-01-25
Online published: 2019-03-29
Supported by
Project supported by the Research Fund Project of Wuhan Institute of Technology (No. K201440), the Pilot Program of Scientific Research Project of Hubei Provincial Department of Education (No. B2016057), the Open Fund of Key Laboratory of New Reactor and Green Chemical Technology of Hubei Provincial (No. 201704).
双四氢异喹啉天然产物是一大类具有较强生物活性的家族,目前已有近百个该类天然产物被陆续报道出来.自1974年Kluepfel等发现了第一个具有抗肿瘤活性的四氢异喹啉天然产物以来,已经有近百个该类四氢异喹啉天然产物被陆续报道出来,目前这类天然产物家族中的双四氢异喹啉生物碱因其优良的生物活性和复杂的化学结构成为了生物学和有机化学研究领域的热点,并进一步推动了该类天然产物家族成员Ecteinasicdin 743(ET-743)在欧盟成功上市,用于治疗晚期软组织瘤和卵巢癌.由于包括ET-743在内的这类双四氢异喹啉天然产物在自然界中含量极低以及化学结构复杂,使得对其化学结构的改造也引起了越来越多的关注.本文基于此,综述了近十年来这类双四氢异喹啉天然产物类似物的研究进展.
杨扬 , 郭举 , 刘站柱 . 抗肿瘤活性双四氢异喹啉生物碱类似物的合成研究进展[J]. 有机化学, 2019 , 39(7) : 1913 -1922 . DOI: 10.6023/cjoc201810037
Since the first tetrahydroisoquinoline alkaloid (THIQ), naphthyridinomycin, was found by Canadian scientist Kluepfel in 1974, nearly hundred members of this family have been reported. Such THIQ has attracted the research interest of many chemists and biologists due to its excellent biological activity and complex chemical structure. Especially, as an outstanding member of THIQ family, Ecteinascidin 743 (ET-743) has been commercialized in the European Union for the treatment of soft tissue tumors and ovarian cancer. Due to the extremely low content of natural products of bistetrahydroisoquinoline including ET-743 and the complexity of its chemical structure, the modification of its chemical structure has attracted more and more attention. Based on this, the recent advance in the synthesis of bistetrahydroisoquinoline analogues is reviewed.
[1] Kluepfel, D.; Baker, H. A.; Piattoni, G.; Sehgal, S. N.; Sidorowicz, A.; Singh, K.; Vezina, C. J. Antibiot. 1975, 28, 497.
[2] Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
[3] Martinez, E. J.; Owa, T.; Schreiber, S. L.; Corey, E. J. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 3496.
[4] Martinez, E. J.; Corey, E. J.; Owa, T. Chem. Biol. 2001, 8, 1151.
[5] Plowright, A. T.; Schaus, S. E.; Myers, A. G. Chem. Biol. 2002, 9, 607.
[6] Cuevas, C.; Manzanares, I.; Perez, M.; Martin, M. J.; Rodriguez, A.; Munt, S. (Pharma Mar, S. A.). ES 2231486 T3, 2003.
[7] Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202.
[8] Eduardo, J. M.; Corey, E. J. Org. Lett. 1999, 1, 75.
[9] Cuevas, C.; Pérez, M.; Martín, M. J.; Chicharro, J. L.; Fernádez, R. C.; Flores, M.; Francesch, A.; Gallego, P.; Zarzuelo, M.; Calle, F.; García, J.; Polanco, C.; Rodríguez, I.; Manzanares, I. Org. Lett. 2000, 2, 2545.
[10] Chen, J.-C.; Chen, X.-C.; Michele, B. C.; Zhu, J.-P. J. Am. Chem. Soc. 2006, 128, 87
[11] Chen, X.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 3962.
[12] Jonathan, W.; Chen, Y.-Y.; Williams, R. M. J. Am. Chem. Soc. 2005, 127, 12684.
[13] Smith, L. H. S.; Nguyen, T. T.; Sneddon, H. F.; Procter, D. J. Chem. Commun. 2011, 47, 10821
[14] Xu, S.-H.; Wang, G.; Zhu, J.-J.; Shen, C.; Yang, Z.-Z.; Yu, J.; Li, Z.; Lin, T.-H.; Sun, X.; Zhang, F.-L. Eur. J. Org. Chem. 2017, 5, 975.
[15] Wang. Y.; Tang, Y.-F.; Liu, Z.-Z.; Chern, S.-Z.; Liang, X.-T. Chin. J. Org. Chem. 2005, 25, 42(in Chinese). (王晔, 唐叶峰, 刘站柱, 陈世智, 梁晓天, 有机化学, 2005, 25, 42.)
[16] Liao, X,-W.; Dong, W.-F.; Liu, W.; Chen, S.-Z.; Liu, Z.-Z. Chin. J. Org. Chem. 2010, 30, 317(in Chinese). (廖祥伟, 董文芳, 刘伟, 陈世智, 刘站柱, 有机化学, 2010, 30, 317.)
[17] Song, Y.-T.; Hu, L.-L.; Chen, R.-J.; Chen, X.-C. Chin. J. Org. Chem. 2015, 35, 1627(in Chinese). (宋玉廷, 胡玲玲, 陈瑞蛟, 陈小川, 有机化学, 2015, 35, 1627.)
[18] Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Kieffer, P. A.; Sun, F.; Li, L.-H.; Martin, D. G. J. Org. Chem. 1990, 55, 4512.
[19] Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Kieffer, P. A.; Sun, F.; Li, L.-H.; Martin, D. G. J. Org. Chem. 1991, 56, 1676.
[20] Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
[21] Zheng, S.; Chan, C.; Furuuchi, T.; Wright, B.; Zhou, B.; Guo. J.; Danishefsky, S. J. J. Angew. Chem., Int. Ed. 2006, 45, 1754.
[22] Jeffrey, R..; Martin, S.; Jason, O.; Peter, S.; Stacie, A. D.; Catherine, M.; Hyunjin, M. K.; Zhang, P-L.; Neil, S.; Katherine, G. M.; Juthamas, S.; Doris, G.; Ohn, E.; Peter, R. Y.; Myers, A. G.; Green, M. J. Bioorg. Med. Chem. Lett. 2006, 16, 4884.
[23] Ocio, E. M.; Maiso, P.; Chen, X.; Garayoa, M.; Alvarez-Fernandez, S.; SanSegundo, L.; Vilanova, D.; Lopez-Corral, L.; Montero, J. C.; HernandezIglesias, T.; Alava, E.; Galmarini, C.; Aviles, P.; Cuevas, C.; Pandiella, A. Blood. 2009, 113, 3781.
[24] Leal, J. F. M.; Garcia-Hernandez, V.; Moneo, V.; Domingo, A.; Bueren-Calabuig, J. A.; Negri, A.; Gago, F.; Guillen-Navarro, M. J.; Aviles, P.; Cuevas, C.; GarciaFernandez, L. F.; Galmarini, C. Biochem. Pharmacol. 2009, 78, 162.
[25] Roberto, M.; Martinez, V.; Alberto, R.; Natividad, R.; Flores, M.; Gallego, P.; Manzanares, I.; Cuevas, C. J. Org. Chem. 2003, 68, 8859.
[26] Plácido, A. C.; Marta, P.; Cuevas, C.; Andrés, F.; Manzanares, I.; Antonio, M.; Echavarren. Eur. J. Org. Chem. 2006, 8, 1926.
[27] Zhou, B.-S.; Guo, J. S.; Danishefsky, S. J. Tetra. Lett. 2000, 41, 2043.
[28] Benjamin, J.; Wright, D.; Collin C.; Danishefsky, S. J. J. Nat. Prod. 2008, 71, 409.
[29] Kubo, A.; Saito, N.; Yamauchi, R.; Sakai, S. Chem. Pharm. Bull. 1987, 35, 2158.
[30] Kubo, A.; Saito, N.; Yamato, H.; Kawakarmi, Y. Chem. Pharm. Bull. 1987, 35, 2525.
[31] Kubo, A.; Saito, N.; Nakamura, M.; Ogata, K.; Sakai, S. Heterocycles 1987, 26, 1765.
[32] Kubo, A.; Saito, N.; Yamato, H.; Yamauchi, R.; Hiruma, K.; Inoue, S. Chem. Pharm. Bull. 1988, 36, 2607.
[33] Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295.
[34] Shinya, K.; Shintaro, K.; Masayuki, A.; Yoshifumi, U.; Koizumi, Y.; Masashi, Y.; Saito, N. Heterocycles 2015, 90, 327.
[35] Masashi, Y.; Ryoko, T.; Toshihiro, S.; Vy, H. L.; Williams, R. M.; Saito, N. J. Org. Chem. 2016, 81, 4039.
[36] Christian, R.; Razafindrabe.; Sylvain, A.; Benjamin B.; Andriantsiferana, M.; Stéphane, P. R.; Lemaire, M. Tetrahedron 2010, 66, 9061.
[37] Kawagishi, F.; Toma, T.; Inui, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2013, 135, 13684.
[38] Chen, R.; Liu, H.; Chen, X. J. Nat. Prod. 2013, 76, 1789.
[39] Chen, R.; Zhu, D.; Hu, Z.; Zheng, Z.; Chen, X. Tetrahedron:Asymmetry 2010, 21, 39.
[40] Chen, R.; Liu, H.; Liu, X.; Chen, X. Tetrahedron 2013, 69, 3565.
[41] Liu, H.; Chen, R.; Chen, X. Org. Biomol. Chem. 2014, 12, 1633.
[42] Jia, J.; Chen, R.; Liu, H.; Li, X.; Jia, Y.; Chen, X. Org. Biomol. Chem. 2016, 14, 7334.
[43] González, J. F.; Cuesta, E.; Avendano, C. Bioorg. Med. Chem. 2007, 15, 112.
[44] Ortín, I.; González, J. F.; Cuesta, E.; Cristina, M. G.; Rosario P.; Avendano, C. Bioorg. Med. Chem. 2008, 16, 9065.
[45] Ortín, I.; González, J. F.; Cuesta, E.; Avendano, C. Tetrahedron 2009, 65, 2201.
[46] Ortín, I.; González, J. F.; Cuesta, E.; Avendano, C. Tetrahedron 2009, 65, 9944.
[47] Ortín, I.; González, J. F.; Cuesta, E.; Avendano, C. Bioorg. Med. Chem. 2010, 18, 6813.
[48] Tuyen, N. V.; Pieter, C.; Norbert, D. K. Synlett 2014, 45, 69.
[49] Tang, Y.-F.; Liu, Z.-Z.; Chen, S.-Z. Tetrahedron Lett. 2003, 44, 7091.
[50] Liao, X.-W.; Liu, W.; Dong, W.-F.; Guan, B.-H.; Chen, S.-Z.; Liu, Z.-Z. Tetrahedron 2009, 65, 5709.
[51] Liu, W.; Dong, W.-F.; Liao, X.-W.; Yan, Z.; Guan, B.-H.; Wang, N.; Liu, Z.-Z. Bioorg. Med. Chem. Lett. 2011, 21, 1419.
[52] Dong, W.-F.; Liu, W.; Liao, X.-W.; Guan, B.-H.; Chen, S.-Z.; Liu, Z.-Z. J. Org. Chem. 2011, 76, 5363.
[53] Liu, W.; Liao, X.-W.; Dong, W.-F.; Yan, Z.; Wang, N.; Liu, Z.-Z. Tetrahedron 2012, 68, 2759.
[54] Dong, W.-F.; Liu. W.; Yan, Z.; Liao, X.-W.; Guan, B.-H.; Wang, N.; Liu, Z.-Z. Eur. J. Med. Chem. 2012, 49, 239.
[55] Liu, Z.-Z.; Wang, Y.; Tang, Y.-F.; Chen, S.-Z.; Chen, X.-G.; Li, H.-Y. Bioorg. Med. Chem. Lett. 2006, 16, 1282.
[56] Guo, J.; Dong, W.-F.; Liu, W.; Yan, Z.; Wang, N.; Liu, Z.-Z. Eur. J. Med. Chem. 2013, 62, 670.
[57] Guo, J.; Yang, Y.; Wang, N.; Liu, Z.-Z. Tetrahedron Lett. 2018, 33, 3202.
[58] Lu, X.-R.; Pan, X.; Yang, Y.; Ji, M.; Chen, X.-G.; Xiao, Z.-Y.; Liu, Z.-Z. Eur. J. Med. Chem. 2017, 135, 260.
[59] Eric, R. W.; Aurapat, N.; Max, K.; Guillaume, L.; Gerit, M. P.; Martina, S. J. M.; Dylan, C.; Christopher, D. G.; Pamela, M. T.; Christopher, K. H.; Kenji, N.; Emil, G.; Christian, U. G.; Kevin, M. A.; Scott, C. V.; Dennis, J. S.; Brian, M. S. Science 2019, 363, 270.
/
〈 |
|
〉 |