介离子化合物的合成与生物活性研究进展

doi:10.6023/cjoc202003064

摘要/Abstract

介离子化合物代表了一类在杂环化学中非常重要的分子，在医药和农药等领域有着广泛的应用.自1935年该类化合物被发现以来，因其有着独特的反应活性和物活性，人们对其合成、应用和性质等方面一直进行研究，不少文献报道了该类化合物的合成及相关活性.综述了几类介离子化合物的合成方法和部分重要机理，并探讨了介离子化合物作为一种优势活性结构在未来的应用前景.

关键词: 介离子化合物, 合成, 生物活性

As an important kind of heterocyclic molecules, mesoionic compounds are widely used in medicine, pesticide and other fields. Ever since they were discovered in 1935, mesoionic compounds have been extensively explored in terms of synthesis, properties and applications. Many references relating to these compounds have been published over years revealing their unique reactivity and bioactivity. An overview of mesoionic compounds from the perspectives of synthetic methods, reaction mechanisms and applications is offered. Their potentials as a dominant active structure for development of pesticides are also discussed.

Key words: mesoionic compound, synthesis, biological activity

引用此文

梁伟, 谭成侠, 翁建全, 刘幸海. 介离子化合物的合成与生物活性研究进展[J]. 有机化学, 2020, 40(9): 2702-2713.

Liang Wei, Tan Chengxia, Weng Jianquan, Liu Xinghai. Advances on Synthesis and Biological Activities of Mesoionic Compounds[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2702-2713.

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参考文献

[1] Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899.
[2] Huisgen, R.; Gotthardt, H.; Bayer, H, O. Angew. Chem., Int. Ed. 1964, 3, 136.
[3] St Cyr, D. J.; Arndtsen, B. A. J. Am. Chem. Soc. 2007, 129, 12366.
[4] Wilton, D. J.; Harrison, R. F.; Willett, P.; Delaney, J.; Lawson, K.; Mullier, G. J. Chem. Inf. Model. 2006, 46, 471.
[5] Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1.
[6] Latthe, P. R.; Shinge, P. S.; Badami, B. V.; Patil, P. B.; Holihosur, S. N. J. Chem. Sci. 2006, 118, 249.
[7] Gotthard, H.; Huisgen, R.; Schaefer, F. C. Tetrahedron Lett. 1964, 10, 487.
[8] Zhang, W. M.; Holyoke, C. W.; Barry, J.; Leighty, R. M.; Cordova, D.; Vincent, D. R.; Briddell, T. A. Bioorg. Med. Chem. Lett. 2016, 26, 5444.
[9] Zhang, W. M. Acc. Chem. Res. 2017, 50, 2381
[10] Holyoke, C. W. Jr.; Cordova, D.; Zhang, W. M.; Barry, D. J.; Leighty, M. R.; Dietrich, F. R.; Rauh, J. J.; Pahutski, F. T. Jr.; Lahm, P. G.; Tong, T. M.-H.; Benner, A. E.; Andreassi, L. J.; Smith, M. R.; Vincent, R. D.; Christianson, A. L.; Teixeira, A. L.; Singh, V.; Hughes, A. K. Pest Manage. Sci. 2017, 73, 796.
[11] Coburn, R. A.; Carapellotti, R. A. J. Pharm. Sci. 1976, 65, 1505.
[12] White, E. H.; Egger, N. J. Am. Chem. Soc. 1984, 106, 3701.
[13] Chandrasekhar, R.; Nanjan, M. J. Mini. Rev. Med. Chem. 2012, 12, 1359.
[14] Jogul, J. J.; Badami, B. V. J. Serb. Chem. Soc. 2006, 71, 851.
[15] Kennis, L. E. J.; Bischoff, F. P.; Mertens, C. J.; Love, C. J.; Keybus, F. A. F. V.; Pieters, S.; Braeken, M.; Megens, A. A. H. P.; Leysen, J. E. Bioorg. Med. Chem. Lett. 2000, 10, 71.
[16] Holyoke Jr, C. W.; Zhang, W. M.; Pahutski, T. F. Jr.; Lahm, G. P.; Tong, M. H. T.; Cordova, D.; Leighty, R. M. 13th IUPAC International Congress of Pesticide Chemistry——Discovery and Synthesis of Crop Protection Products, American Chemical Society, Washington, DC, USA, 2015, pp. 365~378.
[17] Moustafa, M. A.; Gineinah, M. M.; Nasr, M. N.; Bayoumi, W. A. Arch. Pharm. Med. Chem. 2004, 337, 427.
[18] Latthe, P. R.; Shinge, P. S.; Badami, B. V.; Patil, P. B.; Holihosur, S. N. J. Chem. Sci. 2006, 118, 249.
[19] Taj, T.; Kamble, R. R.; Gireesh, T. M.; Hunnur, R. K. J. Serb. Chem. Soc. 2011, 76, 1069.
[20] Patel, K. C.; Patel, H. D. E.-J. Chem. 2011, 8, 113.
[21] Hegde, J. C.; Girish, K. S.; Adhikari, A.; Kalluraya, B. Synth. Commun. 2013, 43, 301.
[22] Dubey, R.; Chaudhary, N.; Kumar, R.; Panwar, H. Orient. J. Chem. 2014, 30, 271.
[23] Bayer, H. O.; Huisgen, R.; Knorr, R.; Schaefer, F. C. Chem. Ber. 1970, 103, 2581.
[24] Potts, K.; Yao, S. J. Org. Chem. 1979, 44, 977
[25] Anderson, A. K.; Heider, A. R. Synth. Commun. 1986, 16, 357.
[26] Kato, H.; Tani, K.; Kurumisawa, H.; Tamura, Y. Chem. Lett. 1980, 717.
[27] Lu, Y.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2008, 47, 5430
[28] (a) Arndtsen, B. A. Chem.-Eur. J. 2009, 15, 302.
(b) Quesenel, J. S.; Amdtsen, B. A. Pure. Appl. Chem. 2013, 85, 377.
[29] Miao, Q.; Sun, H. L. Chin. Sci. Bull. 2015, 60, 2003(in Chinese). (苗群, 孙怀林, 科学通报, 2015, 60, 2003.)
[30] Miao, Q. M.S. Thesis, Nankai University, Tianjin, 2015(in Chinese). (苗群, 硕士论文, 南开大学, 天津, 2015.)
[31] Torres, G. M.; Quesnel, J. S.; Bijou, D.; Arndtsen, B. A. J. Am. Chem. Soc. 2016, 138, 7315.
[32] St Cyr, D. J.; Arndtsen, B. A. J. Am. Chem. Soc. 2007, 129, 12366.
[33] Couture, A.; Deniau, E.; Grandclaudon, P. Synthesis 1994, 953.
[34] Morin, M. S. T.; St Cyr, D. J.; Arndtsen, B. A. Org. Lett. 2010, 12, 4916.
[35] Morin, M. S. T.; Aly, S.; Arndtsen, B. A. Chem Commun. 2013, 49, 883.
[36] Jeanmart, S.; Edmunds, A. F.; Lamberth, C. Bioorg. Med. Chem. 2016, 24, 317.
[37] Holyoke, C. W.; Tong, M. T.; Coats, R. A. WO 099929, 2009.
[38] Lugan, N.; Lavigne, G.; Labande, A.; Cesar, V. Organometallics 2014, 33, 5085.
[39] Zhang, W. M.; Holyoke, W. C. Jr.; Pahutski, F. T. Jr.; Lahm, P. G.; Barry, D. J.; Cordova, D.; Leighty, M. R.; Singh, V.; Vincent, R. D.; Tong, T. M.-H.; Hughes, A. K.; Mc Cann, F. S.; Henry, T. Y.; Xu, M.; Briddell, A. T. Bioorg. Med. Chem. Lett. 2017, 27, 16.
[40] Lei, G. Y.; Ying, J. W.; Song, Y. Q. Mod. Agrochem. 2017, 16, 14(in Chinese). (雷月光, 英君伍, 宋玉泉, 现代农药, 2017, 16, 14.)
[41] Zhang, W. M.; Holyoke, W. C. Jr.; Barry, J.; Cordova, D.; Leighty, M. R.; Tong, T. M.-H.; Hughes, A. K.; Lahm, P. G.; Pahutski, F. T. Jr.; Xu, M.; Briddell, A. T.; Mc Cann, F. T.; Henry, T. Y.; Chen, Y. Z. Bioorg. Med. Chem. Lett. 2017, 27, 911.
[42] (a) Liu, D. Y.; Zhang, J.; Zhao,.L; He, W. J.; Liu, Z. J.; Gan, X. H.; Song, B. A. J. Agric. Food Chem. 2019, 67, 11860.
(b) Pan, J. K. M.S. Thesis, Guizhou University, Guiyang, 2017 (in Chinese). (潘建科, 硕士论文, 贵州大学, 贵阳, 2017.)
[43] Hasegawa, S.; Kamo, T.; Kagohara, Y.; Miyake, T.; Kobayashi, T.; Matsuda, R.; Asano, S.; Kudamatsu, A. WO 171053, 2016.
[44] Thieme, P.; Patsch, M.; Konig, H. Liebigs Ann. Chem. 1972, 764, 94.
[45] Zhang, Z. Y.; Zhu, C. H.; Sun, X. W. Chem. J. Chin. Univ. 2000, 21, 386(in Chinese). (张自义, 褚长虎, 孙小文, 高等学校化学学报, 2000, 21, 386.)
[46] Abbott, P. A.; Bonnert, R. V.; Caffrey, M. V.; Cage, P. A.; Cooke, A. J.; Furber, M.; Hill, S.; Withnall, J. Tetrahedron 2002, 58, 3185.
[47] Avalos, M.; Babiano, R.; Cabanillas, A.; Cintas, P.; Higes, F. J.; Jiménez, J. L.; Palacios, J. C. J. Org. Chem. 1996, 61, 3738.
[48] Arévalo, M. J.; Avalos, M.; Babiano, R.; Cintas, P.; Hursthouse, M. B.; Jiménez, J. L.; Light, M. E.; Palacios, J. C. Tetrahedron:Asymmetry 2002, 13, 223.
[49] Avalos, M.; Babiano, R.; Cintas, P; Jimexnez, J. L.; Palacios, J. C. Acc. Chem. Res. 2005, 38, 460.
[50] Chernyshev, V. N.; Astakhov, A. V.; Starikova, Z. A. Tetrahedron 2010, 66, 3301.
[51] Hassan, A. A.; Bräse. S.; Tawfeek, H. N.; Mohamed, N. K.; Nieger, M.; El-Shaieb, K. M. A. Tetrahedron Lett. 2014, 55, 2385.
[52] Zhao, S. X.; Yu, R. C.; Chen, W. Z.; Liu, M. C.; Wu, H. Y. Org. Lett. 2015, 17, 2828.
[53] Erguven, H.; Leitch, D. C.; Keyzer, E. N.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2017, 56, 6078.
[54] Samarskaya, A. S.; Cherepanov, I. A.; Godovikov, I. A.; Dmitrienko, A. O.; Moiseev, S. K.; Kalinin, V. N.; Hey-Hawkins, E. Tetrahedron 2018, 74, 2693.
[55] Eilertsen, M.; Allin, S. M.; Pearson, R. J. Bioorg. Med. Chem. Lett. 2018, 28, 1106.
[56] (a) He, W. J.; Liu, D. Y.; Gan, X. H.; Zhang, J.; Liu, Z. J.; Yi, C. F.; Song, B. A. Chin. J. Org. Chem. 2019, 39, 2287(in Chinese). (何文静, 刘登曰, 甘秀海, 张建, 刘峥军, 易崇粉, 宋宝安, 有机化学, 2019, 39, 2287.)
(b) He, W. J. M.S. Thesis, Guizhou University, Guiyang, 2019 (in Chinese). (何文静, 硕士论文, 贵州大学, 贵阳, 2019.)
[57] Kuzmina, O. M.; Weisel, M.; Narine, A. A. Eur. J. Org. Chem. 2019, 5527.
[58] Benaissa, A.; Pallova, L.; Morantin, M. E.; Lafitte, T.; Huynh, M.; Barthes, C.; Vendier, L.; Lugan, N.; Bastin, S.; César, V. Chem.-Eur. J. 2019, 3, 242.
[59] Hansmann, M. M.; Antoni, P. W.; Pescht, H. Angew. Chem., Int. Ed. 2020, 59, 2.
[60] Narine, A.; Dickhaut, J.; Kaiser, F.; Bandur, N. G.; Koerber, K.; Von Deyn, W.; Derksen, S.; Paulini, R.; Culbertson, D. L. WO 144228, 2013.
[61] Dickhaut, J.; Narine, A.; Derksen, S.; Bandur, N. G.; Von Deyn, W.; Koller, R.; Wach, J. Y.; Langewald, J.; Rankl, N. B. WO 202582, 2014.
[62] Narine, A.; Bandur, N. G.; Dickhaut, J.; Derksen, S.; Koller, R.; Von Deyn, W.; Wach, J.-Y.; Culbertson, D. L. WO 167084, 2014.
[63] Narine, A.; Dickhaut, J.; Kaiser, F.; Bandur, N. G.; Koerber, K.; Von Deyn, W. WO 033244, 2014.
[64] Dickhaut, J.; Narine, A.; Von Deyn, W.; Koller, R.; Wach, J.-Y.; Vyas, D.; Adisechan, A.; Shinde, H. WO 055431, 2016.
[65] Markus, H.; Daniela, P.; Kerstin, I.; Ulrich, G.; Silvia, C. G.; Marc, M.; Sascha, E.; Andreas, T. WO 093214, 2018.
[66] Heil, M.; Hoffmeister, L.; Webber, M.; Ilg, K.; Goergens, U.; Turberg, A. WO 192872, 2018.
[67] Holyoke, W. C. Jr. WO 208595, 2018.