Citation: Yang Yang, Guo Ju, Liu Zhanzhu. Progress in the Synthesis of Analogues of Bistetrahdro-isoquinoline Antitumor Alkaloids[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1913-1922. doi: 10.6023/cjoc201810037 shu

Progress in the Synthesis of Analogues of Bistetrahdro-isoquinoline Antitumor Alkaloids

Yang Yang ^a ,
Guo Ju ^a,, ,
Liu Zhanzhu ^b,,

a.
Key Laboratory for Green Chemical Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430205
b.
Institute of Materia Medica, China Academy of Medical Sciences & Peking Union Medical College, Beijing 100050

Corresponding author: Guo Ju, guoju1984@163.com Liu Zhanzhu, liuzhanzhu@imm.ac.cn
Received Date: 30 October 2018
Revised Date: 25 January 2019
Available Online: 29 July 2019
Fund Project: the Pilot Program of Scientific Research Project of Hubei Provincial Department of Education B2016057the Open Fund of Key Laboratory of New Reactor and Green Chemical Technology of Hubei Provincial 201704the Research Fund Project of Wuhan Institute of Technology K201440Project 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)

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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.
- antitumor activity,
- bistetrahydroisoquinoline alkaloid,
- analogue,
- research progress
1. [1]
  Kluepfel, D.; Baker, H. A.; Piattoni, G.; Sehgal, S. N.; Sidorowicz, A.; Singh, K.; Vezina, C. J. Antibiot. 1975, 28, 497. doi: 10.7164/antibiotics.28.497
2. [2]
  Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. doi: 10.1021/cr010212u
3. [3]
  Martinez, E. J.; Owa, T.; Schreiber, S. L.; Corey, E. J. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 3496. doi: 10.1073/pnas.96.7.3496
4. [4]
  Martinez, E. J.; Corey, E. J.; Owa, T. Chem. Biol. 2001, 8, 1151. doi: 10.1016/S1074-5521(01)00082-5
5. [5]
  Plowright, A. T.; Schaus, S. E.; Myers, A. G. Chem. Biol. 2002, 9, 607. doi: 10.1016/S1074-5521(02)00137-0
6. [6]
  Cuevas, C.; Manzanares, I.; Perez, M.; Martin, M. J.; Rodriguez, A.; Munt, S. (Pharma Mar, S. A.). ES 2231486 T3, 2003.
7. [7]
  Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202. doi: 10.1021/ja962480t
8. [8]
  Eduardo, J. M.; Corey, E. J. Org. Lett. 1999, 1, 75. doi: 10.1021/ol990553i
9. [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. doi: 10.1021/ol0062502
10. [10]
  Chen, J.-C.; Chen, X.-C.; Michele, B. C.; Zhu, J.-P. J. Am. Chem. Soc. 2006, 128, 87 doi: 10.1021/ja0571794
11. [11]
  Chen, X.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 3962. doi: 10.1002/anie.200700539
12. [12]
  Jonathan, W.; Chen, Y.-Y.; Williams, R. M. J. Am. Chem. Soc. 2005, 127, 12684. doi: 10.1021/ja0535918
13. [13]
  Smith, L. H. S.; Nguyen, T. T.; Sneddon, H. F.; Procter, D. J. Chem. Commun. 2011, 47, 10821 doi: 10.1039/c1cc13992d
14. [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. [15]
  Wang. Y.; Tang, Y.-F.; Liu, Z.-Z.; Chern, S.-Z.; Liang, X.-T. Chin. J. Org. Chem. 2005, 25, 42(in Chinese). doi: 10.3321/j.issn:0253-2786.2005.01.005
16. [16]
  Liao, X, -W.; Dong, W.-F.; Liu, W.; Chen, S.-Z.; Liu, Z.-Z. Chin. J. Org. Chem. 2010, 30, 317(in Chinese).
17. [17]
  Song, Y.-T.; Hu, L.-L.; Chen, R.-J.; Chen, X.-C. Chin. J. Org. Chem. 2015, 35, 1627(in Chinese).
18. [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. doi: 10.1021/jo00302a007
19. [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. doi: 10.1021/jo00004a063
20. [20]
  Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552. doi: 10.1021/ja026216d
21. [21]
  Zheng, S.; Chan, C.; Furuuchi, T.; Wright, B.; Zhou, B.; Guo. J.; Danishefsky, S. J. J. Angew. Chem., Int. Ed. 2006, 45, 1754. doi: 10.1002/anie.200503983
22. [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. doi: 10.1016/j.bmcl.2006.06.085
23. [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. doi: 10.1182/blood-2008-09-177774
24. [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. doi: 10.1016/j.bcp.2009.04.003
25. [25]
  Roberto, M.; Martinez, V.; Alberto, R.; Natividad, R.; Flores, M.; Gallego, P.; Manzanares, I.; Cuevas, C. J. Org. Chem. 2003, 68, 8859. doi: 10.1021/jo034547i
26. [26]
  Plácido, A. C.; Marta, P.; Cuevas, C.; Andrés, F.; Manzanares, I.; Antonio, M.; Echavarren. Eur. J. Org. Chem. 2006, 8, 1926.
27. [27]
  Zhou, B.-S.; Guo, J. S.; Danishefsky, S. J. Tetra. Lett. 2000, 41, 2043. doi: 10.1016/S0040-4039(00)00106-4
28. [28]
  Benjamin, J.; Wright, D.; Collin C.; Danishefsky, S. J. J. Nat. Prod. 2008, 71, 409. doi: 10.1021/np800022x
29. [29]
  Kubo, A.; Saito, N.; Yamauchi, R.; Sakai, S. Chem. Pharm. Bull. 1987, 35, 2158. doi: 10.1248/cpb.35.2158
30. [30]
  Kubo, A.; Saito, N.; Yamato, H.; Kawakarmi, Y. Chem. Pharm. Bull. 1987, 35, 2525. doi: 10.1248/cpb.35.2525
31. [31]
  Kubo, A.; Saito, N.; Nakamura, M.; Ogata, K.; Sakai, S. Heterocycles 1987, 26, 1765. doi: 10.3987/R-1987-07-1765
32. [32]
  Kubo, A.; Saito, N.; Yamato, H.; Yamauchi, R.; Hiruma, K.; Inoue, S. Chem. Pharm. Bull. 1988, 36, 2607. doi: 10.1248/cpb.36.2607
33. [33]
  Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. doi: 10.1021/jo00253a022
34. [34]
  Shinya, K.; Shintaro, K.; Masayuki, A.; Yoshifumi, U.; Koizumi, Y.; Masashi, Y.; Saito, N. Heterocycles 2015, 90, 327. doi: 10.3987/COM-14-S(K)24
35. [35]
  Masashi, Y.; Ryoko, T.; Toshihiro, S.; Vy, H. L.; Williams, R. M.; Saito, N. J. Org. Chem. 2016, 81, 4039. doi: 10.1021/acs.joc.6b00327
36. [36]
  Christian, R.; Razafindrabe.; Sylvain, A.; Benjamin B.; Andriantsiferana, M.; Stéphane, P. R.; Lemaire, M. Tetrahedron 2010, 66, 9061. doi: 10.1016/j.tet.2010.08.053
37. [37]
  Kawagishi, F.; Toma, T.; Inui, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2013, 135, 13684. doi: 10.1021/ja408034x
38. [38]
  Chen, R.; Liu, H.; Chen, X. J. Nat. Prod. 2013, 76, 1789. doi: 10.1021/np400538q
39. [39]
  Chen, R.; Zhu, D.; Hu, Z.; Zheng, Z.; Chen, X. Tetrahedron:Asymmetry 2010, 21, 39. doi: 10.1016/j.tetasy.2009.12.024
40. [40]
  Chen, R.; Liu, H.; Liu, X.; Chen, X. Tetrahedron 2013, 69, 3565. doi: 10.1016/j.tet.2013.02.079
41. [41]
  Liu, H.; Chen, R.; Chen, X. Org. Biomol. Chem. 2014, 12, 1633. doi: 10.1039/c3ob42209g
42. [42]
  Jia, J.; Chen, R.; Liu, H.; Li, X.; Jia, Y.; Chen, X. Org. Biomol. Chem. 2016, 14, 7334. doi: 10.1039/C6OB01064D
43. [43]
  González, J. F.; Cuesta, E.; Avendano, C. Bioorg. Med. Chem. 2007, 15, 112. doi: 10.1016/j.bmc.2006.10.009
44. [44]
  Ortín, I.; González, J. F.; Cuesta, E.; Cristina, M. G.; Rosario P.; Avendano, C. Bioorg. Med. Chem. 2008, 16, 9065. doi: 10.1016/j.bmc.2008.07.083
45. [45]
  Ortín, I.; González, J. F.; Cuesta, E.; Avendano, C. Tetrahedron 2009, 65, 2201. doi: 10.1016/j.tet.2009.01.051
46. [46]
  Ortín, I.; González, J. F.; Cuesta, E.; Avendano, C. Tetrahedron 2009, 65, 9944. doi: 10.1016/j.tet.2009.10.016
47. [47]
  Ortín, I.; González, J. F.; Cuesta, E.; Avendano, C. Bioorg. Med. Chem. 2010, 18, 6813. doi: 10.1016/j.bmc.2010.07.049
48. [48]
  Tuyen, N. V.; Pieter, C.; Norbert, D. K. Synlett 2014, 45, 69.
49. [49]
  Tang, Y.-F.; Liu, Z.-Z.; Chen, S.-Z. Tetrahedron Lett. 2003, 44, 7091. doi: 10.1016/S0040-4039(03)01785-4
50. [50]
  Liao, X.-W.; Liu, W.; Dong, W.-F.; Guan, B.-H.; Chen, S.-Z.; Liu, Z.-Z. Tetrahedron 2009, 65, 5709. doi: 10.1016/j.tet.2009.05.025
51. [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. doi: 10.1016/j.bmcl.2011.01.025
52. [52]
  Dong, W.-F.; Liu, W.; Liao, X.-W.; Guan, B.-H.; Chen, S.-Z.; Liu, Z.-Z. J. Org. Chem. 2011, 76, 5363. doi: 10.1021/jo200758r
53. [53]
  Liu, W.; Liao, X.-W.; Dong, W.-F.; Yan, Z.; Wang, N.; Liu, Z.-Z. Tetrahedron 2012, 68, 2759. doi: 10.1016/j.tet.2012.02.016
54. [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. doi: 10.1016/j.ejmech.2012.01.017
55. [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. doi: 10.1016/j.bmcl.2005.11.069
56. [56]
  Guo, J.; Dong, W.-F.; Liu, W.; Yan, Z.; Wang, N.; Liu, Z.-Z. Eur. J. Med. Chem. 2013, 62, 670. doi: 10.1016/j.ejmech.2013.01.033
57. [57]
  Guo, J.; Yang, Y.; Wang, N.; Liu, Z.-Z. Tetrahedron Lett. 2018, 33, 3202.
58. [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. doi: 10.1016/j.ejmech.2017.04.061
59. [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. doi: 10.1126/science.aav3421
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