综述与进展

3-吲哚羧酸酯类化合物合成方法的研究进展

  • 薛红 ,
  • 董玉 ,
  • 冯磊 ,
  • 李海波 ,
  • 李津 ,
  • 张志伟
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  • 河北科技大学化学与制药工程学院 石家庄 050018

收稿日期: 2017-12-06

  修回日期: 2018-01-06

  网络出版日期: 2018-01-18

基金资助

国家自然科学基金(No.21302039)及河北省自然科学基金(No.B2016208124)资助项目.

Research Progress in the Synthesis of 3-Indolecarboxylates

  • Xue Hong ,
  • Dong Yu ,
  • Feng Lei ,
  • Li Haibo ,
  • Li Jin ,
  • Zhang Zhiwei
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  • College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018

Received date: 2017-12-06

  Revised date: 2018-01-06

  Online published: 2018-01-18

Supported by

Project supported by the National Natural Science Foundation of China (No. 21302039) and the Natural Science Foundation of Hebei Province (No. B2016208124).

摘要

吲哚衍生物因其可以亲和多种受体而被认为是设计药物先导化合物的优势结构.其中,3-吲哚羧酸酯类化合物是广泛存在于天然产物及药物分子中的重要的结构单元,如盐酸阿比多尔、托烷司琼、PD 0298029、Grandilodine A等均为3-吲哚羧酸酯类药物分子或天然产物.基于此,近年来关于3-吲哚羧酸酯类化合物及其衍生物的合成不断地被报道,金属催化的以及非金属条件下的合环反应用来构建吲哚中的吡咯环是近年来研究的热点,而在吲哚C-3位直接进行官能团化合成酯基官能团同样具有较高的效率.在相关研究的基础上,按照上述分类方法,综述了近年来3-吲哚羧酸酯类化合物的合成研究进展.

本文引用格式

薛红 , 董玉 , 冯磊 , 李海波 , 李津 , 张志伟 . 3-吲哚羧酸酯类化合物合成方法的研究进展[J]. 有机化学, 2018 , 38(5) : 1029 -1034 . DOI: 10.6023/cjoc201712010

Abstract

Indole derivatives have been considered as “privileged scaffolds” in drug discovery since they are capable of binding many receptors with high affinity. 3-Indolecarboxylates are widespread structure motifs in many natural products and drug molecules, such as arbidol, tropisetron, PD 0298029, and grandilodine A, etc. Consequently, synthetic studies toward 3-indolecarboxylates have been reported in recent years. Elegant cyclization strategies have been developed via transition-metal catalyzed or transition-metal-free reactions, and direct functionalization at C-3 position for synthesis of ester functional groups was also extremely attractive. Based on our studies toward synthesis of 3-indolecarboxylates, the recent developments of synthesis of 3-indolecarboxylates by different synthetic methods in view of the types of substrates are reviewed.

参考文献

[1] Somei, M.; Yamada, F. Nat. Prod. Rep. 2003, 34, 761.
[2] Zhao, C.; Zhao, Y.; Chai, H.; Gong, P. Bioorg. Med. Chem. 2006, 14, 2552.
[3] Boriskin, Y. S.; Leneva, I. A.; Pecheur, E. I.; Polyak, S. J. Curr. Med. Chem. 2008, 15, 997.
[4] Sheridan, R. P.; Korzekwa, K. R.; Torres, R. A.; Walker, M. J. J. Med. Chem. 2007, 50, 3173.
[5] Augelli-Szafran, C. E.; Jaen, J. C.; Morelang, D. W.; Nelson, C. B.; Penvose-Yi, J. R.; Schwarz, R. D. Bioorg. Med. Chem. Lett. 1998, 8, 1991.
[6] Schultz, E. E.; Pujanauski, B. G.; Sarpong, R. Org. Lett. 2012, 14, 648.
[7] Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195.
[8] Wurtz, S.; Rakshit, S.; Neumann, J. J.; Droge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230.
[9] Sole, D.; Serrano, O. J. Org. Chem. 2008, 73, 2476.
[10] Söderberg, B. C. G.; Banini, S. R.; Turner, M. R.; Minter, A. R.; Arrington, S. K. Synthesis 2008, 903.
[11] Shen, D.; Han, J.; Chen, J.; Deng, H.; Shao, M.; Zhang, H.; Cao, W. Org. Lett. 2015, 17, 3283.
[12] Okuro, K.; Gurnham, J.; Alper, H. J. Org. Chem. 2011, 76, 4715.
[13] Jiang, H.; Gao, S.; Xu, J.; Wu, X.; Lin, A.; Yao, H. Adv. Synth. Catal. 2016, 358, 188.
[14] Yu, K.; Liang, Y.; Li, B.; Wang, B. Adv. Synth. Catal. 2016, 358, 661.
[15] Watanabe, T.; Mutoh, Y.; Saito, S. J. Am. Chem. Soc. 2017, 139, 7749.
[16] Li, H.; Zhao, Y.; Ma, L.; Ma, M.; Jiang, J.; Wan, X. Chem. Commun. 2017, 53, 5993.
[17] Zhang, X.-X.; Sun, X.-P.; Zhang, H.-F.; Cui, X.-L.; Ma, M.-T. Chin. J. Org. Chem. 2015, 35, 1469(in Chinese). (张小祥, 孙小萍, 张海飞, 崔杏丽, 马猛涛, 有机化学, 2015, 35, 1469.)
[18] Lee, K.-Y.; Lee, H.-S.; Kim, J.-N. Bull. Korean Chem. Soc. 2007, 28, 333.
[19] Levesque, P.; Fournier, P. A. J. Org. Chem. 2010, 75, 7033.
[20] Mahavir, P.; Vecchia, L. L.; Kapa, P.; Oljan, R. Synth. Commun. 1995, 25, 95.
[21] Islam, M. S.; Brennan, C.; Wang, Q.; Hossain, M.-M. J. Org. Chem. 2006, 71, 4675.
[22] (a) Natarajan, R.; Rappai, J.; Unnikrishnan, P.; Radhamani, S.; Prathapan, S. Synlett 2015, 26, 2467.
(b) Tang, S.; Gao, X.; Lei, A. Chem. Commum. 2017, 53, 3354.
[23] Peterson, P.; Iii, J. W.; Niemann, C. J. Org. Chem. 1958, 23, 303.
[24] Lang, R.; Wu, J.; Shi, L.; Xia, C.; Li, F. Chem. Commun. 2011, 47, 12553.
[25] Lang, R.; Shi, L.; Li, D.; Xia, C.; Li, F. Org. Lett. 2012, 14, 4130.
[26] Zhang, H.; Liu, D.; Chen, C.; Liu, C.; Lei, A. Chem.-Eur. J. 2011, 17, 9581.
[27] Yang, Q.-Q.; Marchini, M.; Xiao, W.-J.; Ceroni, P.; Bandini, M. Chem.-Eur. J. 2015, 21, 18052.
[28] Nemoto, K.; Tanaka, S.; Konno, M.; Onozawa, S. Tetrahedron 2016, 72, 734.
[29] Zhang, Z.-W.; Xue, H.; Li, H.; Kang, H.; Feng, J.; Lin, A. Org. Lett. 2016, 18, 3918.

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