Chinese Journal of Organic Chemistry >
Research Progress on Synthesis of Thioflavonoids
Received date: 2023-01-05
Revised date: 2023-02-17
Online published: 2023-02-23
Thioflavonoids are the sulfur counterparts of flavonoids, which have a wide range of applications in the fields of medicine, material science, organic synthesis and others. Therefore, it is of great significance to develop efficient synthetic methods to obtain thioflavonoids with diverse structures. The synthetic approaches of thioflavonoids and key steps of reaction mechanisms according to the classification of thioflavonoids are summarized, and the development prospect of this research field is prospected.
Ling Meng , Jun Wang . Research Progress on Synthesis of Thioflavonoids[J]. Chinese Journal of Organic Chemistry, 2023 , 43(3) : 873 -891 . DOI: 10.6023/cjoc202301004
| [1] | (a) Eds.: Andersen, ?. M.; Markham, K. R. Flavonoids: Chemistry, Biochemistry and Applications, Taylor & Francis, London, 2006. |
| [1] | (b) Yan, X.; Liu, H.-Q.; Zou, Y.-Q.; Ren, Z.-H. Chin. J. Org. Chem. 2008, 28, 1534. (in Chinese) |
| [1] | (延玺, 刘会青, 邹永青, 任占华, 有机化学, 2008, 28, 1534.) |
| [1] | (c) Shao, T.; Li, X.; Qi, C.; Chen, G.; Song, X.; Han, C.; Zheng, C. Chin. J. Org. Chem. 2018, 38, 710. (in Chinese) |
| [1] | (邵泰明, 李小宝, 祁翠翠, 陈光英, 宋小平, 韩长日, 郑彩娟, 有机化学, 2018, 38, 710.) |
| [1] | (d) Yang, Q.; Wang, Z.; Hor, C. H. H.; Xiao, H.; Bian, Z.; Wang, J. Sci. Adv. 2022, 8, DOI: 10.1126/sciadv.abm9603. |
| [2] | (a) Brown, M. J.; Carter, P. S.; Fenwick, A. E.; Fosberry, A. P.; Hamprecht, D. W.; Hibbs, M. J.; Jarvest, R. L.; Mensah, L.; Milner, P. H.; O’Hanlon, P. J.; Pope, A. J.; Richardson, C. M.; West, A.; Witty, D. R. Bioorg. Med. Chem. Lett. 2002, 12, 3171. |
| [2] | (b) Zimmer, L.; Fournet, G.; Joseph, B.; Guillaumet, G.; Le Bars, D. Nucl. Med. Biol. 2003, 30, 541. |
| [2] | (c) Kanbe, Y.; Kim, M. H.; Nishimoto, M.; Ohtake, Y.; Tsunenari, T.; Taniguchi, K.; Ohizumi, I.; Kaiho, S.; Nabuchi, Y.; Kawata, S.; Morikawa, K.; Jo, J. C.; Kwon, H. A.; Lim, H. S.; Kim, H. Y. Bioorg. Med. Chem. Lett. 2006, 16, 4090. |
| [2] | (d) Dalla Via, L.; Magno, S. M.; Gia, O.; Marini, A. M.; Da Settimo, F.; Salerno, S.; La Motta, C.; Simorini, F.; Taliani, S.; Lavecchia, A.; Di Giovanni, C.; Brancato, G.; Barone, V.; Novellino, E. J. Med. Chem. 2009, 52, 5429. |
| [2] | (e) Han, X.; Zhong, Y.; Li, S.; Liang, G.; Zhou, G.; Wang, X.; Chen, B.; Song, Y. L. Chem. Pharm. Bull. 2016, 64, 1411. |
| [2] | (f) Urbatzka, R.; Freitas, S.; Palmeira, A.; Almeida, T.; Moreira, J.; Azevedo, C.; Afonso, C.; Correia-da-Silva, M.; Sousa, E.; Pinto, M.; Vasconcelos, V. Eur. J. Med. Chem. 2018, 151, 272. |
| [3] | (a) Nussbaumer, P.; Lehr, P.; Billich, A. J. Med. Chem. 2002, 45, 4310. |
| [3] | (b) Horvath, A.; Nussbaumer, P.; Wolff, B.; Billich, A. J. Med. Chem. 2004, 47, 4268. |
| [3] | (c) Kataoka, T.; Watanabe, S.; Mori, E.; Kadomoto, R.; Tanimura, S.; Kohno, M. Bioorg. Med. Chem. 2004, 12, 2397. |
| [4] | (a) Kitani, S.; Sugawara, K.; Tsutsumi, K.; Morimoto, T.; Kakiuchi, K. Chem. Commun. 2008, 2103. |
| [4] | (b) Hikage, S.; Nishiyama, Y.; Sasaki, Y.; Tanimoto, H.; Morimoto, T.; Kakiuchi, K. ACS Omega 2017, 2, 2300. |
| [5] | (a) Quaglia, W.; Giannella, M.; Piergentili, A.; Pigini, M.; Brasili, L.; Di Toro, R.; Rossetti, L.; Spampinato, S.; Melchiorre, C. J. Med. Chem. 1998, 41, 1557. |
| [5] | (b) Liu, R.; Mabury, S. A. Environ. Sci. Technol. 2018, 52, 10089. |
| [5] | (c) Zhan, T.; Pan, L.; Liu, Z.; Chen, J.; Ge, Z.; Lu, L.; Zhang, X.; Cui, S.; Zhang, C.; Liu, W.; Zhuang, S. Environ. Sci. Technol. 2018, 52, 11904. |
| [5] | (d) Li, J.; Lam, J. C. W.; Li, W.; Du, B.; Chen, H.; Zeng, L. Environ. Sci. Technol. 2019, 53, 10969. |
| [6] | Weerasekare, G. M.; Berlin, K. D.; Sunkara, H.; Ford, W. T. Phosphorus Sulfur 2003, 178, 993. |
| [7] | Liu, J.; Hu, T.; Li, Z.; Wei, X.; Hu, X.; Gao, H.; Liu, G.; Yi, Y.; Yamada-Takamura, Y.; Lee, C. S.; Wang, P.; Wang, Y. J. Phys. Chem. Lett. 2019, 10, 1888. |
| [8] | (a) Nibbs, A. E.; Scheidt, K. A. Eur. J. Org. Chem. 2012, 2012, 449. |
| [8] | (b) Meng, L.; Wang, J. Synlett 2016, 27, 656. |
| [8] | (c) Yang, Q.; Guo, R.; Wang, J. Asian J. Org. Chem. 2019, 8, 1742. |
| [8] | (d) Xiong, L.; Hu, H.; Wei, C.; Yu, B. Eur. J. Org. Chem. 2020, 2020, 1588. |
| [8] | (e) He, Q.-J.; So, C.-M.; Bian, Z.-X.; Hayashi, T.; Wang, J. Chem. Asian. J. 2015, 10, 540. |
| [8] | (f) Lyu, L.-Y.; Jin, M. Y.; He, Q.-J.; Xie. H.; Bian, Z.-X.; Wang, J. Org. Biomol. Chem. 2016, 14, 8088. |
| [8] | (g) Yang, Q.; Wang, Y.; Luo, S.; Wang, J. Angew. Chem., Int. Ed. 2019, 58, 5343. |
| [8] | (h) Cai, B.; Yang, Q.; Meng, L.; Wang, J. Chin. J. Chem. 2021, 39, 1606. |
| [8] | (g) Meng, L.; Liu, H.; Lin, Z.; Wang, J. Org. Lett. 2022, 24, 5890. |
| [9] | (a) Schneller, S. W. InAdvances in Heterocyclic Chemistry, Vol.18, Eds.: Katritzky, A. R.; Boulton, A. J., United States, 1975, pp. 59-97. |
| [9] | (b) Bondock, S.; Metwally, M. A. J. Sulfur Chem. 2008, 29, 623. |
| [10] | (a) Dike, S. Y.; Ner, D. H.; Kumar, A. Bioorg. Med. Chem. Lett. 1991, 1, 383. |
| [10] | (b) van Vliet, L. A.; Rodenhuis, N.; Dijkstra, D.; Wikstrom, H.; Pugsley, T. A.; Serpa, K. A.; Meltzer, L. T.; Heffner, T. G.; Wise, L. D.; Lajiness, M. E.; Huff, R. M.; Svensson, K.; Sundell, S.; Lundmark, M. J. Med. Chem. 2000, 43, 2871. |
| [10] | (c) Choi, E. J.; Lee, J. I.; Kim, G. H. Int. J. Mol. Med. 2012, 29, 252. |
| [10] | (d) Song, J.; Jones, L. M.; Chavarria, G. E.; Charlton-Sevcik, A. K.; Jantz, A.; Johansen, A.; Bayeh, L.; Soeung, V.; Snyder, L. K.; Lade, S. D., Jr.; Chaplin, D. J.; Trawick, M. L.; Pinney, K. G. Bioorg. Med. Chem. Lett. 2013, 23, 2801. |
| [10] | (e) Song, Y. L.; Wu, F.; Zhang, C. C.; Liang, G. C.; Zhou, G.; Yu, J. J. Bioorg. Med. Chem. Lett. 2015, 25, 259. |
| [11] | (a) Clayton, S. E.; Gabbutt, C. D.; Hepworth, J. D.; Heron, B. M. Tetrahedron 1993, 49, 939. |
| [11] | (b) Kumar, P.; Rao, A. T.; Pandey, B. Synth. Commun. 1994, 24, 3297. |
| [11] | (c) Konieczny, M. K.; Horowska, B.; Kunikowski, A.; Konopa, J.; Wierzba, K.; Yamada, Y.; Asao, T. J. Org. Chem. 1999, 64, 359. |
| [11] | (d) Cui, D.-M.; Kawamura, M.; Shimada, S.; Hayashi, T.; Tanaka, M. Tetrahedron Lett. 2003, 44, 4007. |
| [11] | (e) Li, J.; Li, H.; Li, H.; Xiao, L. J. Chem. Res. 2004, 6, 394. |
| [12] | Vaghoo, H.; Prakash, G. K. S.; Narayanan, A.; Choudhary, R.; Paknia, F.; Mathew, T.; Olah, G. A. Org. Lett. 2015, 17, 6170. |
| [13] | Sangeetha, S.; Muthupandi, P.; Sekar, G. Org. Lett. 2015, 17, 6006. |
| [14] | Bouisseau, A.; Glancy, J.; Willis, M. C. Org. Lett. 2016, 18, 5676. |
| [15] | Guo, F.; Jeffries, M. C.; Graves, B. N.; Graham, S. A.; Pollard, D. A.; Pang, G.; Chen, H. Y. Tetrahedron 2017, 73, 5745. |
| [16] | Chen, X.-L.; Tang, B.-C.; He, C.; Ma, J.-T.; Zhuang, S.-Y.; Wu, Y.-D.; Wu, A.-X. Chem. Commun. 2020, 53, 13653. |
| [17] | Nandy, A.; Sekar, G. J. Org. Chem. 2022, 87, 7536. |
| [18] | Meng, L.; Jin, M. Y.; Wang, J. Org. Lett. 2016, 18, 4986. |
| [19] | Luo, S.; Meng, L.; Yang, Q.; Wang, J. Synlett 2018, 29, 2071. |
| [20] | Vila, C.; Hornillos, V.; Fananas-Mastral, M.; Feringa, B. L. Chem. Commun. 2013, 49, 5933. |
| [21] | Trost, B. M.; Gnanamani, E.; Kalnmals, C. A.; Hung, C.; Tracy, J. S. J. Am. Chem. Soc. 2019, 141, 1489. |
| [22] | Meng, L.; Ngai, K. Y.; Chang, X.; Lin, Z.; Wang, J. Org. Lett. 2020, 22, 1155. |
| [23] | Zhao, D.; Beiring, B.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 8454. |
| [24] | Xiong, D.; Zhou, W.; Lu, Z.; Zeng, S.; Wang, J. Chem. Commun. 2017, 53, 6844. |
| [25] | Kerr, M. S.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298. |
| [26] | Li, W.; Liu, X.; Hao, X.; Hu, X.; Chu, Y.; Cao, W.; Qin, S.; Hu, C.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2011, 133, 15268. |
| [27] | Paladhi, S.; Liu, Y.; Kumar, B. S.; Jung, M.-J.; Park, S. Y.; Yan, H.; Song, C. E. Org. Lett. 2017, 19, 3279. |
| [28] | Li, Y.-P.; Li, Z.-Q.; Zhou, B.; Li, M.-L.; Xue, X.-S.; Zhu, S.-F.; Zhou, Q.-L. ACS Catal. 2019, 9, 6522. |
| [29] | Chen, C.-Y.; Yang, C.-H.; Hu, W.-P.; Vandavasi, J. K.; Chunga, M.-I.; Wang, J.-J. RSC Adv. 2013, 3, 2710. |
| [30] | Muthupandi, P.; Sundaravelu, N.; Sekar, G. J. Org. Chem. 2017, 82, 1936. |
| [31] | Le, T. T. H.; Youhei, C.; Le, Q. H.; Nguyen, T. B.; Mac, D. H. Org. Biomol. Chem. 2019, 17, 6355. |
| [32] | Velasco, N.; Suárez, A.; Martínez-Lara, F.; Fernández-Rodríguez, M. á.; Sanz, R.; Suárez-Pantiga, S. J. Org. Chem. 2021, 86, 7078. |
| [33] | Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354. |
| [34] | Rios, R.; Sundén, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Córdova, A. Tetrahedron Lett. 2006, 47, 8547. |
| [35] | Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036. |
| [36] | Zu, L.; Xie, H.; Li, H.; Wang, J.; Jiang, W.; Wang, W. Adv. Synth. Catal. 2007, 349, 1882. |
| [37] | Zhao, G.-L.; Vesely, J.; Rios, R.; Ibrahem, I.; Sundén, H.; Córdova, A. Adv. Synth. Catal. 2008, 350, 237. |
| [38] | Dodda, R.; Goldman, J. J.; Mandal, T.; Zhao, C.-G.; Broker, G. A.; Tiekink, E. R. T. Adv. Synth. Catal. 2008, 350, 537. |
| [39] | Dong, X.-Q.; Fang, X.; Tao, H.-Y.; Zhou, X.; Wang, C.-J. Chem. Commun. 2012, 48, 7238. |
| [40] | Choudhurya, A. R.; Mukherjee, S. Adv. Synth. Catal. 2013, 355, 1989. |
| [41] | Arai, T.; Yamamoto, Y. Org. Lett. 2014, 16, 1700. |
| [42] | Zhao, B.-L.; Du, D.-M. Asian J. Org. Chem. 2015, 4, 778. |
| [43] | Zhu, Y.; Dong, Z.; Cheng, X.; Zhong, X.; Liu, X.; Lin, L.; Shen, Z.; Yang, P.; Li, Y.; Wang, H.; Yan, W.; Wang, K.; Wang, R. Org. Lett. 2016, 18, 3546. |
| [44] | Ahlemeyer, N. A.; Birman, V. B. Org. Lett. 2016, 18, 3454. |
| [45] | Arai, T.; Miyazaki, T.; Ogawa, H.; Masu, H. Org. Lett. 2016, 18, 5824. |
| [46] | Arai, T.; Suzuki, T.; Inoue, T.; Kuwano, S. Synlett 2017, 28, 122. |
| [47] | Simlandy, A. K.; Mukherjee, S. J. Org. Chem. 2017, 82, 4851. |
| [48] | Zhao, B.-L.; Du, D.-M. Org. Lett. 2017, 19, 1036. |
| [49] | Zhang, Y.-P.; You, Y.; Zhao, J.-Q.; Zhang, X.-M.; Xu, X.-Y.; Yuan, W.-C. J. Org. Chem. 2019, 84, 7984. |
| [50] | Wang, M.-M.; Jeon, S.; Waser, J. Org. Lett. 2020, 22, 9123. |
| [51] | Sundaravelu, N.; Nandy, A.; Sekar, G. Org. Lett. 2021, 23, 3115. |
| [52] | Ji, K.; Lu, K.; Huang, J.; Li, Z.-H.; Ke, H.; Chen, Z.-M. Org. Lett. 2021, 23, 8028. |
| [53] | Ji, K.; Lu, K.; Huang, J.; Li, Z.-H.; Ding, T.-M.; Chen, Z.-M. Chem. Commun. 2021, 57, 12639. |
| [54] | Zaitseva, E. R.; Sokolov, A. I.; Mikhaylov, A. A.; Baleeva, N. S.; Baranov, M. S.; Smirnov, A. Y. Chem. Heterocycl. Compd. 2022, 58, 477. |
| [55] | Fukamizu, K.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2008, 130, 10498. |
| [56] | Wang, X.-F.; An, J.; Zhang, X.-X.; Tan, F.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2011, 13, 808. |
| [57] | Lu, H.; Zhang, J.-L.; Liu, J.-Y.; Li, H.-Y.; Xu, P.-F. ACS Catal. 2017, 7, 7797. |
| [58] | Ahlemeyer, N. A.; Streff, E. V.; Muthupandi, P.; Birman, V. B. Org. Lett. 2017, 19, 6486. |
| [59] | Mo, Y.; Zhang, X.; Yao, Y.; Duan, C.; Ye, L.; Shi, Z.; Zhao, Z.; Li, X. J. Org. Chem. 2021, 86, 4448. |
| [60] | (a) Gu, X.; Meng, L.; Li, M.; Wang, J. Org. Chem. Front. 2021, 8, 1563. |
| [60] | (b) Yang. Q.; Li, S.; Wang, J. ChemCatChem 2020, 12, 3202. |
| [61] | Virumbrales, C.; El-Remaily, M. A. E. A. A. A.; Suárez-Pantiga, S.; Fernández-Rodríguez, M. A.; Rodríguez, F.; Sanz, R. Org. Lett. 2022, 24, 8077. |
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