综述与进展

Renieramycin类生物碱的合成研究进展

  • 宋玉廷 ,
  • 胡玲玲 ,
  • 陈瑞蛟 ,
  • 陈小川
展开
  • a 四川大学化学学院 绿色化学与技术教育部重点实验室 成都 610064;
    b 济宁医学院 济宁 272067

收稿日期: 2015-04-01

  修回日期: 2015-04-22

  网络出版日期: 2015-05-06

基金资助

国家自然科学基金(Nos. 21172153, 21321061)、国家重点基础研究发展规划(973计划, No. 2010CB833200)资助项目.

Research Progress in Synthesis of Renieramycin-Type Alkaloids

  • Song Yuting ,
  • Hu Lingling ,
  • Chen Ruijiao ,
  • Chen Xiaochuan
Expand
  • a Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064;
    b Jining Medical College, Jining 272067

Received date: 2015-04-01

  Revised date: 2015-04-22

  Online published: 2015-05-06

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172153, 21321061), the National Basic Research Program of China (973 Program, No. 2010CB833200).

摘要

具有显著抗癌、抗菌等活性的海洋四氢异喹啉生物碱引起多个领域的广泛关注, renieramycin型生物碱目前是其中成员数目最多的一类. 不少此类生物碱及衍生物显示纳摩尔级的抗癌活性, 加上有趣的分子结构, 使其成为有机合成研究的一个热点. 按合成策略分类, 概述了renieramycin型生物碱的全合成研究进展.

本文引用格式

宋玉廷 , 胡玲玲 , 陈瑞蛟 , 陈小川 . Renieramycin类生物碱的合成研究进展[J]. 有机化学, 2015 , 35(8) : 1627 -1640 . DOI: 10.6023/cjoc201504003

Abstract

Marine tetrahydroisoquinoline alkaloids have attracted much attention in the fields of chemistry, biology and medicine over the past forty years because of their remarkable antitumor and antimicrobial activities. Among them, renieramycins is a big group, which consists of renieramycins A~Y, jorunnamycins A~C and jorumycin. A number of renieramycins and their analogues showed nanomolar inhibitory effects in a panel of human tumor cell lines. Therefore, along with other tetrahydroisoquinoline antitumor antibiotics, renieramycins are one of hotspots in the synthetic study of natural products. Progresses on the synthesis of renieramycin-type alkaloids are reviewed in terms of the key strategies employed.

参考文献

[1] (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Siengalewicz, P.; Rinner, U.; Mulzer, J. Chem. Soc. Rev. 2008, 37, 2676.
[2] (a) Rinehart, K. L. Med. Res. Rev. 2000, 20, 1. (b) Avendano, C.; de la Cuesta, E. Curr. Org. Synth. 2009, 6, 143. (c) Tang M.; Tang G. Chin. J. Org. Chem. 2012, 32, 1568 (in Chinese). (韩莹, 孙晶, 孙岩, 高红, 颜朝国, 有机化学, 2012, 32, 1568.)
[3] Frincke, J. M.; Faulkner, D. J. J. Am. Chem. Soc. 1982, 104, 265.
[4] (a) Wright, A. E.; Forleo, D. A.; Gunawardana, G. P.; Gunasekera, S. P.; Koehn, F. E.; McConnell, O. J. J. Org. Chem. 1990, 55, 4508. (b) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Keifer, P. A.; Sun, F.; Li, L. H.; Martin, D. G. J. Org. Chem. 1990, 55, 4512. (c) Sakai, R.; Rinehart, K. L.; Guan, Y.; Wang, A. H.-J. Proc. Natl. Acad. Sci. U. S. A. 1992, 89, 11456. (d) Sakai, R.; Jares-Erijman, E. A.; Manzanares, I.; Elipe, M. V. S.; Rinehart, K. L. J. Am. Chem. Soc. 1996, 118, 9017. (e) Tian, M.; Li, S.; Row, K. Chin. J. Chem. 2012, 30, 43.
[5] (a) Schoffski, P.; Wolter, P.; Clement, P.; Sciot, R.; Wever, I. D.; Wozniak, A.; Stefan, C.; Dumez, H. Future Oncol. 2007, 3, 381. (b) Carter, N. J.; Keam, S. J. Drugs 2007, 67, 2257. (c) Cuevas, C.; Francesch, A. Nat. Prod. Rep. 2009, 26, 322. (d) Molinski, T. F.; Dalisay, D. S.; Lievens, S. L.; Saludes, J. P. Nat. Rev. Drug Discovery 2009, 8, 69.
[6] Brodowicz, T. Future Oncol. 2014, 10(8 Suppl.), 1.
[7] (a) Ding, Z. W.; Tang, H.; Zhang, W. Pharm. Care Res. 2011, 11, 325 (in Chinese). (丁肇卫, 汤华, 张文, 药学服务与研究, 2011, 11, 325.) (b) Blay, J.-Y. Future Oncol. 2014, 10(8 Suppl.), 7. (c) Zanardi, E.; Maruzzo, M.; Montesco, M. C.; Roma, A.; Rastrelli, M.; Basso, U. Anticancer Drug 2014, 25, 1227. (d) Mascilini, F.; Amadio, G.; Di Stefano, M. G.; Ludovisi, M.; Di Legge, A.; Conte, C.; De Vincenzo, R.; Ricci, C.; Masciullo, V.; Salutari, V.; Scambia, G.; Ferrandina, G. OncoTargets Ther. 2014, 7, 1273.
[8] For the total synthesis of ecteinascidin 743, see: (a) Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202. (b) Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552. (c) Chen, J.; Chen, X.; Bois-Choussy, M.; Zhu, J. J. Am. Chem. Soc. 2006, 128, 87. (d) Kawagishi, F.; Toma, T.; Inui, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2013, 135, 13684.
[9] For the formal total synthesis of ecteinascidin 743, see: (a) Zheng, S.; Chan, C.; Furuuchi, T.; Wright, B. J. D.; Zhou, B.; Guo, J.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2006, 45, 1754. (b) Fishlock, D.; Williams, R. M. J. Org. Chem. 2008, 73, 9594.
[10] For the total synthesis of ecteinascidin 770, see: Chen, J.; Chen, X.; Willot, M.; Zhu, J. Angew. Chem., Int. Ed. 2006, 45, 8028.
[11] For the semisynthesis of ecteinascidin 743 and other ecteinascidins, see: (a) Cuevas, C.; Pérez, M.; Martin, M. J.; Chicharro, J. L.; Fernández-Rivas, C.; Flores, M.; Francesch, A.; Gallego, P.; Zarzuelo, M.; de la Calle, F.; García, J.; Polanco, C.; Rodríguez, I.; Manzanares, I. Org. Lett. 2000, 2, 2545. (b) Menchaca, R.; Martínez, V.; Rodríguez, A.; Rodríguez, N.; Flores, M.; Gallego, P.; Manzanares, I.; Cuevas, C. J. Org. Chem. 2003, 68, 8859.
[12] Charupant, K.; Suwanborirux, K.; Amnuoypol, S.; Saito, E.; Kubo, A.; Saito, N. Chem. Pharm. Bull. 2007, 55, 81.
[13] Fontana,A.; Cavaliere, P.; Wahidulla, S.; Naik, C. G.; Cimino, G. Tetrahedron 2000, 56, 7305.
[14] (a) Saito, N.; Tanaka, C.; Koizumi, Y.; Suwanborirux, K.; Amnuoypol, S.; Pummangura, S.; Kubo, A. Tetrahedron 2004, 60, 3873. (b) Charupant, K.; Daikuhara, N.; Saito, E.; Amnuoypol, S.; Suwanborirux, K.; Owa, T.; Saito, N. Bioorg. Med. Chem. 2009, 17, 4548. (c) Liu, W.; Liao, X.; Dong, W.; Yan, Z.; Wang, N.; Liu, Z. Tetrahedron 2012, 68, 2759.
[15] Fukuyama, T.; Linton, S. D.; Tun, M. M. Tetrahedron Lett. 1990, 31, 5989.
[16] Godfrey, I. M.; Sargent, M. V.; Elix, J. A. J. Chem. Soc., Perkin Trans. 1 1974, 1353.
[17] Davidson, B. S. Tetrahedron Lett. 1992, 33, 3721.
[18] Yokoya, M.; Shinada-Fujino, K.; Saito, N. Tetrahedron Lett. 2011, 52, 2446.
[19] Yokoya, M.; Shinada-Fujino, K.; Yoshida, S.; Mimura, M.; Takada, H.; Saito, N. Tetrahedron 2012, 68, 4166.
[20] (a) Parameswaran, P. S.; Naik, C. G.; Kamat, S. Y.; Pramanik, B. N. Indian J. Chem., 1998, 37B, 1258. (b) Pettit, G. R.; Knight, J. C.; Collins, J. C.; Herald, D. L.; Pettit, R. K.; Boyd, M. R.; Young, V. G. J. Nat. Prod. 2000, 63, 793. (c) Saito, N.; Sakai, H.; Suwanborirux, K.; Pummangura, S.; Kubo, A. Heterocycles 2001, 55, 21.
[21] (a) Yokoya, M.; Ito, H.; Saito, N. Chem. Pharm. Bull. 2011, 59, 787. (b) Yokoya, M.; Ito, H.; Saito, N. Tetrahedron 2011, 67, 9185.
[22] Matsuo, K.; Okumura, M.; Tanaka, T. Chem. Pharm. Bull. 1982, 30, 4170.
[23] Kubo A.; Saito N.; Yamato H.; Kawakami Y.; Chem. Pharm. Bull. 1987, 35, 2525.
[24] Lane, J. W.; Chen, Y.; Williams, R. M. J. Am. Chem. Soc. 2005, 127, 12684.
[25] Jin, W.; Williams, R. M. Tetrahedron Lett. 2003, 44, 4635.
[26] Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957.
[27] (a) Magnus, P.; Matthews, K. S. J. Am. Chem. Soc. 2005, 127, 12476. (b) Magnus, P.; Matthews, K. S. Tetrahedron 2012, 68, 6343.
[28] (a) 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. (b) 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.
[29] Chan, C.; Heid, R.; Zheng, S.; Guo, J.; Zhou, B.; Furuuchi, T.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127, 4596.
[30] Sinhababu, A. K.; Ghosh, A. K.; Borchardt, R. T. J. Med. Chem. 1985, 28, 1273.
[31] Vincent, G.; Williams, R. M. Angew. Chem. Int. Ed. 2007, 46, 1517.
[32] Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3783.
[33] Chen, X.; Zhu, J. Angew. Chem. Int. Ed. 2007, 46, 3962.
[34] Liao, X. W.; Liu, W.; Dong, W. F.; Guan, B. H.; Chen, S. Z.; Liu, Z. Z. Tetrahedron 2009, 65, 5709.
[35] Wu, Y.-C.; Zhu, J. Org. Lett. 2009, 11, 5558.
[36] Suwanborirux, K.; Amnuoypol, S.; Plubrukarn, A.; Pummangura, S.; Kubo, A.; Tanaka,C.; Saito, N. J. Nat. Prod. 2003, 66, 1441.
[37] (a) Chen, X.; Chen, J.; Paolis, M. D.; Zhu, J. J. Org. Chem. 2005, 70, 4397. (b) Vincent, G.; Lane, J. W.; Williams, R. M. Tetrahedron Lett. 2007, 48, 3719. (c) Liao, X. W.; Dong, W. F.; Liu, W.; Guan, B. H.; Liu, Z. Z. J. Heterocycl. Chem. 2011, 48, 414.
[38] (a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322. (b) Obika, S.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem. 2008, 73, 5206.
[39] Chen, R.; Liu, H.; Chen, X. J. Nat. Prod. 2013, 76, 1789.
[40] (a) Chen, R.; Zhu, D.; Hu, Z.; Zheng, Z.; Chen, X. Tetrahedron: Asymmetry 2010, 21, 39. (b) Chen, R.; Liu, H.; Liu, X.; Chen, X. Tetrahedron 2013, 69, 3565.
[41] Tatsukawa, M.; Punzalan, L. L. C.; Magpantay, H. D.S.; Villaseñor, I. M.; Concepcion, G. P.; Suwanborirux, K.; Yokoya, M.; Saito, N. Tetrahedron 2012, 68, 7422.
[42] Liu, H.; Chen, R.; Chen, X. Org. Biomol. Chem. 2014, 12, 1633.
[43] (a) Liu, Z.-Z.; Wang, Y.; Tang, Y.-F.; Chen, S.-Z.; Chen, X.-G.; Li, H.-Y. Bioorg. Med. Chem. Lett. 2006, 16, 1282. (b) Otrín, I.; González, J. F.; de la Cuesta, E.; Manguan-García, C.; Perona, R.; Avendaño, C.; Bioorg. Med. Chem. 2008, 16, 9065. (c) Otrín, I.; González, J. F.; de la Cuesta, E.; Avendaño, C.; Tetrahedron 2009, 65, 2201. (d) Otrín, I.; González, J. F.; de la Cuesta, E.; Avendaño, C.; Tetrahedron 2009, 65, 9944. (e) Pan, L.; Chen, R.; Ni, D.; Xia, L.; Chen, X. Synlett 2013, 241. (f) Nakai, K.; Yokoya, M.; Saito, N. Chem. Pharm. Bull. 2013, 61, 853. (g) Nakai, K.; Kubo, K.; Yokoya, M.; Saito, N. Tetrahedron 2014, 70, 6529.

文章导航

/