Citation: 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. doi: 10.6023/cjoc202003064 shu

Advances on Synthesis and Biological Activities of Mesoionic Compounds

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Liu Xinghai, xhliu@zjut.edu.cn
Received Date: 29 March 2020
Revised Date: 13 May 2020
Available Online: 29 May 2020
Fund Project: the Natural Science Foundation of Zhejiang Province LY19C140002Project supported by the Natural Science Foundation of Zhejiang Province (No. LY19C140002)

Figures(33)

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.
- mesoionic compound,
- synthesis,
- biological activity
1. [1]
  Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899. doi: 10.1039/jr9350000899
2. [2]
  Huisgen, R.; Gotthardt, H.; Bayer, H, O. Angew. Chem., Int. Ed. 1964, 3, 136. doi: 10.1002/anie.196401361
3. [3]
  St Cyr, D. J.; Arndtsen, B. A. J. Am. Chem. Soc. 2007, 129, 12366. doi: 10.1021/ja074330w
4. [4]
  Wilton, D. J.; Harrison, R. F.; Willett, P.; Delaney, J.; Lawson, K.; Mullier, G. J. Chem. Inf. Model. 2006, 46, 471. doi: 10.1021/ci050397w
5. [5]
  Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1. doi: 10.1016/S0065-2725(08)60230-5
6. [6]
  Latthe, P. R.; Shinge, P. S.; Badami, B. V.; Patil, P. B.; Holihosur, S. N. J. Chem. Sci. 2006, 118, 249. doi: 10.1007/BF02708284
7. [7]
  Gotthard, H.; Huisgen, R.; Schaefer, F. C. Tetrahedron Lett. 1964, 10, 487.
8. [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. doi: 10.1016/j.bmcl.2016.10.031
9. [9]
  Zhang, W. M. Acc. Chem. Res. 2017, 50, 2381 doi: 10.1021/acs.accounts.7b00311
10. [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. doi: 10.1002/ps.4496
11. [11]
  Coburn, R. A.; Carapellotti, R. A. J. Pharm. Sci. 1976, 65, 1505. doi: 10.1002/jps.2600651022
12. [12]
  White, E. H.; Egger, N. J. Am. Chem. Soc. 1984, 106, 3701. doi: 10.1021/ja00324a067
13. [13]
  Chandrasekhar, R.; Nanjan, M. J. Mini. Rev. Med. Chem. 2012, 12, 1359.
14. [14]
  Jogul, J. J.; Badami, B. V. J. Serb. Chem. Soc. 2006, 71, 851. doi: 10.2298/JSC0609851J
15. [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. doi: 10.1016/S0960-894X(99)00591-0
16. [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. [17]
  Moustafa, M. A.; Gineinah, M. M.; Nasr, M. N.; Bayoumi, W. A. Arch. Pharm. Med. Chem. 2004, 337, 427. doi: 10.1002/ardp.200300847
18. [18]
  Latthe, P. R.; Shinge, P. S.; Badami, B. V.; Patil, P. B.; Holihosur, S. N. J. Chem. Sci. 2006, 118, 249. doi: 10.1007/BF02708284
19. [19]
  Taj, T.; Kamble, R. R.; Gireesh, T. M.; Hunnur, R. K. J. Serb. Chem. Soc. 2011, 76, 1069. doi: 10.2298/JSC100708085T
20. [20]
  Patel, K. C.; Patel, H. D. E.-J. Chem. 2011, 8, 113. doi: 10.1155/2011/705856
21. [21]
  Hegde, J. C.; Girish, K. S.; Adhikari, A.; Kalluraya, B. Synth. Commun. 2013, 43, 301. doi: 10.1080/00397911.2011.599102
22. [22]
  Dubey, R.; Chaudhary, N.; Kumar, R.; Panwar, H. Orient. J. Chem. 2014, 30, 271. doi: 10.13005/ojc/300134
23. [23]
  Bayer, H. O.; Huisgen, R.; Knorr, R.; Schaefer, F. C. Chem. Ber. 1970, 103, 2581. doi: 10.1002/cber.19701030830
24. [24]
  Potts, K.; Yao, S. J. Org. Chem. 1979, 44, 977 doi: 10.1021/jo01320a020
25. [25]
  Anderson, A. K.; Heider, A. R. Synth. Commun. 1986, 16, 357. doi: 10.1080/00397918608076318
26. [26]
  Kato, H.; Tani, K.; Kurumisawa, H.; Tamura, Y. Chem. Lett. 1980, 717.
27. [27]
  Lu, Y.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2008, 47, 5430 doi: 10.1002/anie.200801385
28. [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. [29]
  Miao, Q.; Sun, H. L. Chin. Sci. Bull. 2015, 60, 2003 (in Chinese).
30. [30]
  Miao, Q. M.S. Thesis, Nankai University, Tianjin, 2015 (in Chinese).
31. [31]
  Torres, G. M.; Quesnel, J. S.; Bijou, D.; Arndtsen, B. A. J. Am. Chem. Soc. 2016, 138, 7315. doi: 10.1021/jacs.6b02314
32. [32]
  St Cyr, D. J.; Arndtsen, B. A. J. Am. Chem. Soc. 2007, 129, 12366. doi: 10.1021/ja074330w
33. [33]
  Couture, A.; Deniau, E.; Grandclaudon, P. Synthesis 1994, 953.
34. [34]
  Morin, M. S. T.; St Cyr, D. J.; Arndtsen, B. A. Org. Lett. 2010, 12, 4916. doi: 10.1021/ol102075y
35. [35]
  Morin, M. S. T.; Aly, S.; Arndtsen, B. A. Chem Commun. 2013, 49, 883. doi: 10.1039/C2CC38274A
36. [36]
  Jeanmart, S.; Edmunds, A. F.; Lamberth, C. Bioorg. Med. Chem. 2016, 24, 317. doi: 10.1016/j.bmc.2015.12.014
37. [37]
  Holyoke, C. W.; Tong, M. T.; Coats, R. A. WO 099929, 2009.
38. [38]
  Lugan, N.; Lavigne, G.; Labande, A.; Cesar, V. Organometallics 2014, 33, 5085. doi: 10.1021/om5007819
39. [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. doi: 10.1016/j.bmcl.2016.11.042
40. [40]
  Lei, G. Y.; Ying, J. W.; Song, Y. Q. Mod. Agrochem. 2017, 16, 14 (in Chinese).
41. [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. doi: 10.1016/j.bmcl.2017.01.002
42. [42]
43. [43]
  Hasegawa, S.; Kamo, T.; Kagohara, Y.; Miyake, T.; Kobayashi, T.; Matsuda, R.; Asano, S.; Kudamatsu, A. WO 171053, 2016.
44. [44]
  Thieme, P.; Patsch, M.; Konig, H. Liebigs Ann. Chem. 1972, 764, 94.
45. [45]
  Zhang, Z. Y.; Zhu, C. H.; Sun, X. W. Chem. J. Chin. Univ. 2000, 21, 386 (in Chinese).
46. [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. doi: 10.1016/S0040-4020(02)00269-7
47. [47]
  Avalos, M.; Babiano, R.; Cabanillas, A.; Cintas, P.; Higes, F. J.; Jiménez, J. L.; Palacios, J. C. J. Org. Chem. 1996, 61, 3738. doi: 10.1021/jo952275g
48. [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. doi: 10.1016/S0957-4166(02)00104-0
49. [49]
  Avalos, M.; Babiano, R.; Cintas, P; Jimexnez, J. L.; Palacios, J. C. Acc. Chem. Res. 2005, 38, 460. doi: 10.1021/ar040212r
50. [50]
  Chernyshev, V. N.; Astakhov, A. V.; Starikova, Z. A. Tetrahedron 2010, 66, 3301. doi: 10.1016/j.tet.2010.03.009
51. [51]
  Hassan, A. A.; Bräse. S.; Tawfeek, H. N.; Mohamed, N. K.; Nieger, M.; El-Shaieb, K. M. A. Tetrahedron Lett. 2014, 55, 2385. doi: 10.1016/j.tetlet.2014.02.107
52. [52]
  Zhao, S. X.; Yu, R. C.; Chen, W. Z.; Liu, M. C.; Wu, H. Y. Org. Lett. 2015, 17, 2828. doi: 10.1021/acs.orglett.5b01247
53. [53]
  Erguven, H.; Leitch, D. C.; Keyzer, E. N.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2017, 56, 6078. doi: 10.1002/anie.201609726
54. [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. doi: 10.1016/j.tet.2018.04.015
55. [55]
  Eilertsen, M.; Allin, S. M.; Pearson, R. J. Bioorg. Med. Chem. Lett. 2018, 28, 1106. doi: 10.1016/j.bmcl.2018.01.059
56. [56]
57. [57]
  Kuzmina, O. M.; Weisel, M.; Narine, A. A. Eur. J. Org. Chem. 2019, 5527.
58. [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. [59]
  Hansmann, M. M.; Antoni, P. W.; Pescht, H. Angew. Chem., Int. Ed. 2020, 59, 2. doi: 10.1002/anie.201914768
60. [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. [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. [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. [63]
  Narine, A.; Dickhaut, J.; Kaiser, F.; Bandur, N. G.; Koerber, K.; Von Deyn, W. WO 033244, 2014.
64. [64]
  Dickhaut, J.; Narine, A.; Von Deyn, W.; Koller, R.; Wach, J.-Y.; Vyas, D.; Adisechan, A.; Shinde, H. WO 055431, 2016.
65. [65]
  Markus, H.; Daniela, P.; Kerstin, I.; Ulrich, G.; Silvia, C. G.; Marc, M.; Sascha, E.; Andreas, T. WO 093214, 2018.
66. [66]
  Heil, M.; Hoffmeister, L.; Webber, M.; Ilg, K.; Goergens, U.; Turberg, A. WO 192872, 2018.
67. [67]
  Holyoke, W. C. Jr. WO 208595, 2018.
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
4. [4]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
5. [5]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
6. [6]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
7. [7]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
8. [8]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
9. [9]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
10. [10]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
11. [11]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
12. [12]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
13. [13]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
14. [14]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
15. [15]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
16. [16]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
17. [17]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
18. [18]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
19. [19]
  Zhifang SU , Zongjie GUAN , Yu FANG . Process of electrocatalytic synthesis of small molecule substances by porous framework materials. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2373-2395. doi: 10.11862/CJIC.20240290
20. [20]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094

Get Citation

PDF

XML

Metrics

PDF Downloads(31)
Abstract views(2538)
HTML views(842)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142