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2023 , Vol. 43 >Issue 3: 826 - 854

DOI: https://doi.org/10.6023/cjoc202211046

综述与进展

稠杂环化合物的合成及其抗肿瘤活性研究进展

  • 段康慧 ,
  • 唐俊龙 ,
  • 伍婉卿
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  • 华南理工大学化学与化工学院 广东省功能分子工程重点实验室 广州 510640

收稿日期: 2022-11-30

  修回日期: 2023-02-15

  网络出版日期: 2023-03-01

基金资助

国家自然科学基金(22071063)

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Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities

  • Kanghui Duan ,
  • Junlong Tang ,
  • Wanqing Wu
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  • Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640
* Corresponding author. E-mail:

Received date: 2022-11-30

  Revised date: 2023-02-15

  Online published: 2023-03-01

Supported by

National Natural Science Foundation of China(22071063)

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摘要

稠杂环化合物具有独特的物理化学性质, 在天然产物全合成、超导材料、储能材料、高分子材料以及有机染料等领域具有广泛应用, 而过渡金属催化是构建碳-碳键及碳-杂键的重要手段之一, 近年来过渡金属催化不饱和烃的反应迅猛发展, 具有合成步骤简单、原子经济性强、原料成本低等特点, 引起了化学家的广泛关注和浓厚研究兴趣. 在此, 总结归纳了近五年涉及过渡金属催化不饱和烃合成苯并呋喃、吲哚、喹啉等稠杂环化合物的反应及其机制，并介绍了稠杂环化合物在抗肿瘤方面的应用.

关键词： 不饱和烃; 过渡金属催化; 稠杂环化合物; 抗肿瘤活性

本文引用格式

段康慧 , 唐俊龙 , 伍婉卿 . 稠杂环化合物的合成及其抗肿瘤活性研究进展[J]. 有机化学, 2023 , 43(3) : 826 -854 . DOI: 10.6023/cjoc202211046

Abstract

The unique physicochemical properties invest fused heterocyclic compounds with wide applications in the synthesis of natural products, drugs, superconducting materials, energy storage materials, polymer materials, organic dyes, etc. In recent years, the rapid development of transition metal-catalyzed reactions of unsaturated hydrocarbons has developed rapidly. Owing to the advantages of high step- and atom-economy, easy availability of raw starting materials, and efficient construction of carbon-carbon bonds or/and carbon-hetero bonds, it is a vital way to synthesize fused heterocyclic compounds. Herein, the recent progress on the reaction development of transition metal-catalyzed cyclizations involving unsaturated hydrocarbons for the synthesis of fused heterocyclic compounds including benzofurans, indoles, quinolines in the last five years has been summarized, as well as their applications in the field of medicinal chemistry with antitumor activities.

Key words： unsaturated hydrocarbons; transition metal-catalysis; fused heterocyclic compounds; antitumor activity

参考文献

[1]
Abd El Razik, H. A.; Wahab, A. E. Arch. Pharm. 2011, 344, 184.
[2]
Ahmed, O. M.; Mohamed, M. A.; Ahmed, R. R.; Ahmed, S. A. Eur. J. Med. Chem. 2009, 44, 3519.
[3]
An, Z.; Wu, M.; Kang, J.; Ni, J.; Qi, Z.; Yuan, B.; Yan, R. Eur. J. Org. Chem. 2018, 2018, 4812.
[4]
Blass, B. ACS Med. Chem. Lett. 2012, 3, 616.
[5]
Hassan, A. S.; Masoud, D. M.; Sroor, F. M.; Askar, A. A. Med. Chem. Res. 2017, 26, 2909.
[6]
Hassan, A. Y.; Mohamed, M. A.; Abdel-Aziem, A.; Hussain, A. O. Polycycl. Aromat. Compd. 2020, 40, 1280.
[7]
Komuraiah, B.; Ren, Y.; Xue, M.; Cheng, B.; Liu, J.; Liu, Y.; Chen, J. Chem. Biol. Drug Des. 2021, 97, 1109.
[8]
Liu, Y.; Zhang, X. H.; Ren, J.; Jin, G. Y. Synth. Commun. 2004, 34, 151.
[9]
Panda, S.; Roy, A.; Deka, S. J.; Trivedi, V.; Manna, D. ACS. Med. Chem. Lett. 2016, 7, 1167.
[10]
Tsyshevsky, R.; Smirnov, A. S.; Kuklja, M. M. J. Phys. Chem. C 2019, 123, 8688.
[11]
Zhang, H.; Wang, Q.; Huang, L.; Tian, Z.; Zhang, S.; Zhang, Y. Tetrahedron Lett. 2021, 72, 153070.
[12]
Fujihara, T. Asian J. Org. Chem. 2022, e202200535.
[13]
Gong, L.-Z.; Wang, P.-S.; Shen, M.-L. Synthesis 2018, 50, 956.
[14]
Li, B.-J.; Sun, X. Synthesis 2022, 54, 2103.
[15]
Shi, Z.; Li, N.; Lu, H.-K.; Chen, X.; Zheng, H.; Yuan, Y.; Ye, K.-Y. Curr. Opin. Electrochem. 2021, 28, 100713.
[16]
Shi, Y.; Xiao, T.; Xia, D.; Yang, W. Chin. J. Org. Chem. 2022, 42, 2715. (in Chinese)
[16]
(石云, 肖婷, 夏冬, 杨文超, 有机化学, 2022, 42, 2715.)
[17]
Dawood, K. M. Expert Opin. Ther. Pat. 2019, 29, 841.
[18]
Hofer, K. E.; Faber, K.; Muller, D. M.; Hauffe, T.; Wenger, U.; Kupferschmidt, H.; Rauber-Luthy, C. Ann. Emerg. Med. 2017, 69, 79.
[19]
Khanam, H.; Shamsuzzaman Eur. J. Med. Chem. 2015, 97, 483.
[20]
Radadiya, A.; Shah, A. Eur. J. Med. Chem. 2015, 97, 356.
[21]
Termentzi, A.; Khouri, I.; Gaslonde, T.; Prado, S.; Saint-Joanis, B.; Bardou, F.; Amanatiadou, E. P.; Vizirianakis, I. S.; Kordulakova, J.; Jackson, M.; Brosch, R.; Janin, Y. L.; Daffe, M.; Tillequin, F.; Michel, S. Eur. J. Med. Chem. 2010, 45, 5833.
[22]
Xu, Z.; Zhao, S.; Lv, Z.; Feng, L.; Wang, Y.; Zhang, F.; Bai, L.; Deng, J. Eur. J. Med. Chem. 2019, 162, 266.
[23]
Wu, W.; Yi, S.; Huang, W.; Luo, D.; Jiang, H. Org. Lett. 2017, 19, 2825.
[24]
Hu, W.; Li, M.; Jiang, G.; Wu, W.; Jiang, H. Org. Lett. 2018, 20, 3500.
[25]
Guo, S.; Li, P.; Guan, Z.; Cai, L.; Chen, S.; Lin, A.; Yao, H. Org. Lett. 2019, 21, 921.
[26]
Iqbal, N.; Iqbal, N.; Maiti, D.; Cho, E. J. Angew. Chem., Int. Ed. 2019, 58, 15808.
[27]
He, J.; Xue, Y.; Han, B.; Zhang, C.; Wang, Y.; Zhu, S. Angew. Chem., Int. Ed. 2020, 59, 2328.
[28]
Lin, Z.; Jin, Y.; Hu, W.; Wang, C. Chem. Sci. 2021, 12, 6712.
[29]
Zhou, F.; Li, C.; Li, M.; Jin, Y.; Jiang, H.; Zhang, Y.; Wu, W. Chem. Commun. 2021, 57, 4799.
[30]
Liu, Y.; Luo, W.; Xia, T.; Fang, Y.; Du, C.; Jin, X.; Li, Y.; Zhang, L.; Lei, W.; Wu, H. Org. Chem. Front. 2021, 8, 1732.
[31]
Chripkova, M.; Zigo, F.; Mojzis, J. Molecules 2016, 21, 1626.
[32]
Singh, T. P.; Singh, O. M. Mini-Rev. Med. Chem. 2018, 18, 9.
[33]
Warskulat, A. C.; Tatsis, E. C.; Dudek, B.; Kai, M.; Lorenz, S.; Schneider, B. ChemBioChem 2016, 17, 318.
[34]
Baeyer, A.; Knop, C. A. Ann. Pharm. 1866, 140, 1.
[35]
Kong, W.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2017, 56, 3987.
[36]
Zhang, W.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2017, 56, 5336.
[37]
Liu, Y.-Z.; Shang, S.-J.; Zhu, J.-Y.; Yang, W.-L.; Deng, W.-P. Adv. Synth. Catal. 2018, 360, 2191.
[38]
Zheng, X.; Yang, W.-L.; Liu, Y.-Z.; Wu, S.-X.; Deng, W.-P. Adv. Synth. Catal. 2018, 360, 2843.
[39]
Wang, K.; Ding, Z.; Zhou, Z.; Kong, W. J. Am. Chem. Soc. 2018, 140, 12364.
[40]
Loup, J.; Larin, E. M.; Lautens, M. Angew. Chem., Int. Ed. 2021, 60, 22345.
[41]
Chen, J.; Han, X.; Lu, X. Angew. Chem., Int. Ed. 2017, 56, 14698.
[42]
Kolli, M. K.; Shaik, N. M.; Chandrasekar, G.; Chidara, S.; Korupolu, R. B. New J. Chem. 2017, 41, 8187.
[43]
Li, J.; Li, C.; Ouyang, L.; Li, C.; Wu, W.; Jiang, H. Org. Biomol. Chem. 2017, 15, 7898.
[44]
Luo, Y. G.; Basha, R. S.; Reddy, D. M.; Xue, Y. J.; Chen, T. H.; Lee, C. F. Org. Lett. 2018, 20, 6872.
[45]
He, Y. P.; Wu, H.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2020, 59, 2105.
[46]
Cheng, C.; Zuo, X.; Tu, D.; Wan, B.; Zhang, Y. Org. Lett. 2020, 22, 4985.
[47]
Fan, L.; Hao, J.; Yu, J.; Ma, X.; Liu, J.; Luan, X. J. Am. Chem. Soc. 2020, 142, 6698.
[48]
Wu, J.; Li, L.; Liu, M.; Bai, L.; Luan, X. Angew. Chem., Int. Ed. 2022, 61, e202113820.
[49]
Hu, X.-D.; Chen, Z.-H.; Zhao, J.; Sun, R.-Z.; Zhang, H.; Qi, X.; Liu, W.-B. J. Am. Chem. Soc. 2021, 143, 3734.
[50]
Arora, R.; Rodriguez, J. F.; Whyte, A.; Lautens, M. Angew. Chem., Int. Ed. 2022, 61, e202112288.
[51]
Baruah, S.; Saikia, P.; Duarah, G.; Gogoi, S. Org. Lett. 2018, 20, 3753.
[52]
Shang, Y.; Jonnada, K.; Yedage, S. L.; Tu, H.; Zhang, X.; Lou, X.; Huang, S.; Su, W. Chem. Commun. 2019, 55, 9547.
[53]
Xu, Y.; Shen, M.; Zhang, X.; Fan, X. Org. Lett. 2020, 22, 4697.
[54]
Voth, C. N.; Dake, G. R. Eur. J. Org. Chem. 2020, 2020, 744.
[55]
Wang, H. R.; Huang, E. H.; Luo, C.; Luo, W. F.; Xu, Y.; Qian, P. C.; Zhou, J. M.; Ye, L. W. Chem. Commun. 2020, 56, 4832.
[56]
Clarke, A. K.; Rossi-Ashton, J. A.; Taylor, R. J. K.; Unsworth, W. P. Tetrahedron 2020, 76, 131392.
[57]
Yuan, K.; Liu, L.; Chen, J.; Guo, S.; Yao, H.; Lin, A. Org. Lett. 2018, 20, 3477.
[58]
Rodriguez, J. F.; Marchese, A. D.; Lautens, M. Org. Lett. 2018, 20, 4367.
[59]
Irfan, A.; Batool, F.; Zahra Naqvi, S. A.; Islam, A.; Osman, S. M.; Nocentini, A.; Alissa, S. A.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2020, 35, 265.
[60]
Pathak, N.; Rathi, E.; Kumar, N.; Kini, S. G.; Rao, C. M. Mini-Rev. Med. Chem. 2020, 20, 12.
[61]
Williams, N. S.; Gonzales, S.; Naidoo, J.; Rivera-Cancel, G.; Voruganti, S.; Mallipeddi, P.; Theodoropoulos, P. C.; Geboers, S.; Chen, H.; Ortiz, F.; Posner, B.; Nijhawan, D.; Ready, J. M. J. Med. Chem. 2020, 63, 9773.
[62]
Shen, G.; Yang, B.; Huang, X.; Hou, Y.; Gao, H.; Cui, J.; Cui, C.; Zhang, T. J. Org. Chem. 2017, 82, 3798.
[63]
Huang, Y.; Yan, D.; Wang, X.; Zhou, P.; Wu, W.; Jiang, H. Chem. Commun. 2018, 54, 1742.
[64]
Zhou, P.; Huang, Y.; Wu, W.; Yu, W.; Li, J.; Zhu, Z.; Jiang, H. Org. Biomol. Chem. 2019, 17, 3424.
[65]
Moon, S.; Kato, M.; Nishii, Y.; Miura, M. Adv. Synth. Catal. 2020, 362, 1669.
[66]
Assis, L. C.; de Castro, A. A.; de Jesus, J. P. A.; Nepovimova, E.; Kuca, K.; Ramalho, T. C.; La Porta, F. A. Sci. Rep. 2021, 11, 6397.
[67]
Narwal, S.; Kumar, S.; Verma, P. K. Res. Chem. Intermed. 2016, 43, 2765.
[68]
Horák, R.; Ko?istek, K.; ?am?ulová, V.; Slaninová, L.; Grepl, M.; Kvapil, L.; Funk, P.; Hradil, P.; Soural, M. J. Heterocycl. Chem. 2020, 57, 1605.
[69]
Kaishap, P. P.; Duarah, G.; Chetia, D.; Gogoi, S. Org. Biomol. Chem. 2017, 15, 3491.
[70]
Zhang, X.; Han, X.; Chen, J.; Lu, X. Tetrahedron 2017, 73, 1541.
[71]
Cen, J.; Li, J.; Zhang, Y.; Zhu, Z.; Yang, S.; Jiang, H. Org. Lett. 2018, 20, 4434.
[72]
Ranjith Kumar, G.; Kumar, R.; Rajesh, M.; Sridhar Reddy, M. Chem. Commun. 2018, 54, 759.
[73]
Wang, X.; He, D.; Huang, Y.; Fan, Q.; Wu, W.; Jiang, H. J. Org. Chem. 2018, 83, 5458.
[74]
Mule, R. D.; Shaikh, A. C.; Gade, A. B.; Patil, N. T. Chem. Commun. 2018, 54, 11909.
[75]
Shaikh, A. C.; Banerjee, S.; Mule, R. D.; Bera, S.; Patil, N. T. J. Org. Chem. 2019, 84, 4120.
[76]
Chintawar, C. C.; Mane, M. V.; Tathe, A. G.; Biswas, S.; Patil, N. T. Org. Lett. 2019, 21, 7109.
[77]
De Abreu, M.; Tang, Y.; Brachet, E.; Selkti, M.; Michelet, V.; Belmont, P. Org. Biomol. Chem. 2021, 19, 1037.
[78]
Liao, J.; Fan, L.; Guo, W.; Zhang, Z.; Li, J.; Zhu, C.; Ren, Y.; Wu, W.; Jiang, H. Org. Lett. 2017, 19, 1008.
[79]
Cai, S.; Lin, S.; Yi, X.; Xi, C. J. Org. Chem. 2017, 82, 512.
[80]
Zhang, Z. M.; Xu, B.; Wu, L.; Wu, Y.; Qian, Y.; Zhou, L.; Liu, Y.; Zhang, J. Angew. Chem., Int. Ed. 2019, 58, 14653.
[81]
Tyagi, A.; Reshi, N. U. D.; Daw, P.; Bera, J. K. Dalton. Trans. 2020, 49, 15238.
[82]
Li, J.; Tang, H.; Lin, Z.; Yang, S.; Wu, W.; Jiang, H. Org. Biomol. Chem. 2020, 18, 4071.
[83]
Zhang, P.; Wang, C.; Cui, M.; Du, M.; Li, W.; Jia, Z.; Zhao, Q. Org. Lett. 2020, 22, 1149.
[84]
Pan, Q.; Ping, Y.; Wang, Y.; Guo, Y.; Kong, W. J. Am. Chem. Soc. 2021, 143, 10282.
[85]
Bajohr, J.; Diallo, A. G.; Whyte, A.; Gaillard, S.; Renaud, J. L.; Lautens, M. Org. Lett. 2021, 23, 2797.
[86]
Dong, J.; Bao, L.; Hu, Z.; Ma, S.; Zhou, X.; Hao, M.; Li, N.; Xu, X. Org. Lett. 2018, 20, 1244.
[87]
Guo, S.; Pan, R.; Guan, Z.; Li, P.; Cai, L.; Chen, S.; Lin, A.; Yao, H. Org. Lett. 2019, 21, 6320.
[88]
Saha, R.; Arunprasath, D.; Sekar, G. J. Catal. 2019, 377, 673.
[89]
Hong, F. L.; Wang, Z. S.; Wei, D. D.; Zhai, T. Y.; Deng, G. C.; Lu, X.; Liu, R. S.; Ye, L. W. J. Am. Chem. Soc. 2019, 141, 16961.
[90]
Liu, X.; Wang, Z. S.; Zhai, T. Y.; Luo, C.; Zhang, Y. P.; Chen, Y. B.; Deng, C.; Liu, R. S.; Ye, L. W. Angew. Chem., Int. Ed. 2020, 59, 17984.
[91]
Whyte, A.; Bajohr, J.; Arora, R.; Torelli, A.; Lautens, M. Angew. Chem., Int. Ed. 2021, 60, 20231.
[92]
Wu, Y.; Xu, B.; Zhao, G.; Pan, Z.; Zhang, Z. M.; Zhang, J. Chin. J. Chem. 2021, 39, 3255.
[93]
Li, J. F.; Xu, W. W.; Wang, R. H.; Li, Y.; Yin, G.; Ye, M. Nat. Commun. 2021, 12, 3070.
[94]
Jin, L. P.; Xie, Q.; Huang, E. F.; Wang, L.; Zhang, B. Q.; Hu, J. S.; Wan, D. C.; Jin, Z.; Hu, C. Bioorg. Chem. 2020, 95, 103566.
[95]
Li, Q.; Jian, X. E.; Chen, Z. R.; Chen, L.; Huo, X. S.; Li, Z. H.; You, W. W.; Rao, J. J.; Zhao, P. L. Bioorg. Chem. 2020, 102, 104076.
[96]
Romagnoli, R.; Baraldi, P. G.; Sarkar, T.; Carrion, M. D.; Cruz-Lopez, O.; Lopez Cara, C.; Tolomeo, M.; Grimaudo, S.; Di Cristina, A.; Pipitone, M. R.; Balzarini, J.; Gambari, R.; Ilaria, L.; Saletti, R.; Brancale, A.; Hamel, E. Bioorg. Med. Chem. 2008, 16, 8419.
[97]
Hu, H.; Li, Q.; Li, Z.; Li, W.; Zhang, F.; Chen, H. Chem. Res. Appl. 2019, 31, 511. (in Chinese)
[97]
(胡鸿雨, 李全涛, 李正辉, 李威威, 张发饶, 陈红征, 化学研究与应用, 2019, 31, 511.)
[98]
Iacopetta, D.; Catalano, A.; Ceramella, J.; Barbarossa, A.; Carocci, A.; Fazio, A.; La Torre, C.; Caruso, A.; Ponassi, M.; Rosano, C.; Franchini, C.; Sinicropi, M. S. Bioorg. Chem. 2020, 105, 104440.
[99]
Fu, D. J.; Cui, X. X.; Zhu, T.; Zhang, Y. B.; Hu, Y. Y.; Zhang, L. R.; Wang, S. H.; Zhang, S. Y. Bioorg. Chem. 2021, 107, 104634.
[100]
Jia, H. W.; Yang, H. L.; Xiong, Z. L.; Deng, M. H.; Wang, T.; Liu, Y.; Cheng, M. Bioorg. Chem. 2022, 129, 106213.
[101]
Abdelgawad, M. A.; Belal, A.; Ahmed, O. M. J. Chem. Pharm. Res. 2013, 5, 318.
[102]
Seenaiah, D.; Reddy, P. R.; Reddy, G. M.; Padmavathi, V.; Krishna, N. S. Eur. J. Med. Chem. 2014, 77, 1.
[103]
Gabr, M. T.; El-Gohary, N. S.; El-Bendary, E. R.; El-Kerdawy, M. M.; Ni, N. Chin. Chem. Lett. 2016, 27, 380.
[104]
Diao, P. C.; Lin, W. Y.; Jian, X. E.; Li, Y. H.; You, W. W.; Zhao, P. L. Eur. J. Med. Chem. 2019, 179, 196.
[105]
Abd El-Meguid, E. A.; Mohi El-Deen, E. M.; Moustafa, G. O.; Awad, H. M.; Nossier, E. S. Bioorg. Chem. 2022, 119, 105504.
[106]
Vennila, K. N.; Sunny, D.; Madhuri, S.; Ciattini, S.; Chelazzi, L.; Elango, K. P. Bioorg. Chem. 2018, 81, 184.
[107]
Abdelsalam, E. A.; Zaghary, W. A.; Amin, K. M.; Abou Taleb, N. A.; Mekawey, A. A. I.; Eldehna, W. M.; Abdel-Aziz, H. A.; Hammad, S. F. Bioorg. Chem. 2019, 89, 102985.
[108]
Akkachairin, B.; Rodphon, W.; Reamtong, O.; Mungthin, M.; Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S. Bioorg. Chem. 2020, 98, 103732.
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