超声促进CuSO4/NaAsc水相中高效催化合成N-苯磺酰基苯乙酰胺及其抑制种子萌发的研究
收稿日期: 2022-01-10
修回日期: 2022-02-12
网络出版日期: 2022-03-22
基金资助
湖南省自然科学基金青年项目(2021JJ40515); 湖南省教育厅科学研究(21B0677)
Efficient Ultrasound-Assisted Approach to N-Benzensulfonyl Phenylacetamide via CuSO4/NaAsc Catalysis in Water and Its Inhibition Activity of Seed Germination
Received date: 2022-01-10
Revised date: 2022-02-12
Online published: 2022-03-22
Supported by
Natural Science Foundation of Hunan Province Youth Project(2021JJ40515); Scientific Research Fund of Hunan Provincial Education Department(21B0677)
为了高效、高收率地获得新型N-苯磺酰基苯乙酰胺脱落酸类似物, 取代苯乙炔和苯磺酰叠氮为起始原料, 水相中超声辐射下经廉价的CuSO4/NaAsc (NaAsc为抗坏血酸钠)催化获得32个目标化合物. 该方法操作简单、收率高(86%~95%)、溶剂环保. 种子萌发实验结果表明, 25和50 µmol/L目标化合物处理后大豆种子发芽明显受阻, 其中22个目标化合物处理后抑制率为100%, 活性优于脱落酸(ABA). 该结果有利于快速地合成具有高抑制萌发活性的新型脱落酸类似物
关键词： 硫酸铜/抗坏血酸钠; 超声辐射; N-苯磺酰基苯乙酰胺; 脱落酸类似物; 抑制种子萌发
黄志友 , 李哲陟 , 何波 , 李文胜 , 杨平 , 陈立军 . 超声促进CuSO4/NaAsc水相中高效催化合成N-苯磺酰基苯乙酰胺及其抑制种子萌发的研究[J]. 有机化学, 2022 , 42(6) : 1667 -1676 . DOI: 10.6023/cjoc202201010
Substituted phenylene and benzenesulfonyl-azides were used as starting materials to obtain N-benzensulfonyl phenylacetamide abscisic mimics (PACs). 32 target compounds were efficiently and quickly obtained via cheap combination of CuSO4/NaAsc (NaAsc, sodium ascorbate) catalysis under ultrasonic radiation in water (86%~95%). Furthermore, 22 target compounds could overwhelmingly inhibit soybean seed germination at the concentration of 50 and 25 µml/L. These results are benefit to discovering novel seed germination inhibitor agents.
| [1] | Li, Z. X.; Takahashi, Y.; Scavo, A.; Brandt, B.; Nguyen, D.; Rieu, P.; Schroeder, J. I. Proc. Natl. Acad. Sci. U. S. A. 2018, 115, 4522. |
| [2] | Jurkiewicz, P.; Batoko, H. Plant Sci. 2018, 267, 48. |
| [3] | Park, S. Y.; Peterson, F. C.; Mosquna, A.; Yao, J.; Volkman, B. F.; Cutler, S. R. Nature 2015, 520, 545. |
| [4] | Hampson, C. R.; Reaney, M. J. T.; Abrams, G. D.; Abrams, S. R.; Gusta, L. V. Phytochemistry. 1992, 31, 2645. |
| [5] | Verslues, P. E.; Zhu, J. New developments in abscisic acid perception and metabolism. Curr. Opin. Plant Biol. 2007, 10, 447. |
| [6] | Han, X. Q.; Xiao, Y. M.; Lu, H. Z.; Qian, Z. H. Chin. Bull. Botany. 2013, 48, 329. (in Chinese) |
| [6] | ( 韩小强, 肖玉梅, 路慧哲, 覃兆海, 植物学报, 2013, 48, 329.) |
| [7] | Han, X. Q.; Wan, C.; Yang, D. Y.; Du, S. J.; Yuan, X. Y.; Xiao, Y. M.; Qin, Z. H. Chin. J. Org. Chem. 2014, 34, 1692. (in Chinese) |
| [7] | ( 韩小强, 万川, 杨冬燕, 杜士杰, 袁小勇, 肖玉梅, 覃兆海, 有机化学, 2014, 34, 1692.) |
| [8] | Ma, Y.; Szostkiewicz, I.; Korte, A.; Moes, D.; Yang, Y.; Christmann, A.; Grill, E. Science 2009, 324, 1064. |
| [9] | Park, S.; Fung, P.; Nishimura, N.; Jensen, D. R.; Fujii, H.; Zhao, Y.; Lumba, S.; Santiago, J.; Rodrigues, A.; Chow, T. F. Science 2009, 324, 1068. |
| [10] | Cao, M.; Liu, X.; Zhang, Y.; Xue, X.; Zhou, X. E.; Melcher, K.; Gao, P.; Wang, F.; Zeng, L.; Zhao, Y. Cell Res. 2013, 23, 1043. |
| [11] | Okamoto, M.; Peterson, F. C.; Defries, A.; Park, S.; Endo, A.; Nambara, E.; Volkman, B. F.; Cutler, S. R. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 12132. |
| [12] | Duan, L. S.; Yu, C. X.; Liu, S. J.; Hu, T. L.; Zhou, Y. Y.; Li, Z. H. WO 2018086507, 2018. |
| [13] | Che, C. L.; Hu, Y. M.; Ding, S. S.; Xiao, Y. M.; Li, J. Q.; Qin, Z. H. Chin. J. Org. Chem. 2019, 39, 419. (in Chinese) |
| [13] | ( 车传亮, 胡益敏, 丁珊珊, 肖玉梅, 李佳奇, 覃兆海, 有机化学, 2019, 39, 419.) |
| [14] | Yang, G. F.; Huang, Z. Y.; Hao, G. F. CN 107372504, 2016. |
| [15] | Yang, G. F.; Huang, Z. Y.; Hao, G. F. CN 107382842, 2017. |
| [16] | Huang, Z. Y.; Liu, M.; Mao, Y. J.; Chen, Y. D.; Wang, Y. P.; Liu, C. Tetrahedron Lett. 2019, 60, 626. |
| [17] | Zhao, T.; Meng, Q.; Sun, Z. S.; Chen, Y. Y.; Ai, W.; Zhao, Z.; Kang, D. W.; Dong, Y.; Liang, R. P.; Wu, T.; Pang, J. X.; Liu, X. Y.; Zhan, P. J. Med. Chem. 2020, 63, 10829. |
| [18] | Ammazzalorso, A.; De Filippis, B.; Giampietro, L.; Amoroso, R. Chem. Biol. Drug Des. 2017, 90, 1094. |
| [19] | Kim, S. O.; Duffy, D. M. Biol. Reprod. 2016, 95. |
| [20] | Asada, M.; Obitsu, T.; Kinoshita, A.; Nakai, Y.; Nagase, T.; Sugimoto, I.; Tanaka, M.; Takizawa, H.; Yoshikawa, K.; Sato, K.; Narita, M.; Ohuchida, S.; Nakai, H.; Toda, M. Bioorg. Med. Chem. Lett. 2010, 20, 2639. |
| [21] | Winum, J. Y.; Scozzafava, A.; Montero, J. L.; Supuran, C. T. Med. Res. Rev. 2006, 26, 767. |
| [22] | Luo, Y.; Li, Y.; Qiu, K. M.; Lu, X.; Fu, J.; Zhu, H. L. Bioorg. Med. Chem. 2011, 19, 6069. |
| [23] | Wang, Y.; Sarris, K.; Sauer, D. R.; Djuric, S. W. Tetrahedron Lett. 2007, 48, 5181. |
| [24] | Shen, S.; Chai, Y.; Liu, Y.; Li, C.; Pan, Y. Org. Biomol. Chem. 2015, 13, 10205. |
| [25] | Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046. |
| [26] | Zhang, W. S.; Xu, W. J.; Kuang, C. X. Chin. J. Org. Chem. 2015, 35, 2059. (in Chinese) |
| [26] | ( 张文生, 许文静, 匡春香, 有机化学, 2015, 35, 2059.) |
| [27] | Mittersteiner, M.; Farias, F. F. S.; Bonacorso, H. G.; Martins, M. A. P.; Zanatta, N. Ultrason. Sonochem. 2021, 79. |
| [28] | Zhang, Z. G.; Yan, X. Q.; Zhang, G. S.; Liu, Q. F.; Ma, N. N.; Liu, T. X.; Shi, L. Tetrahedron 2016, 72, 3077. |
| [29] | Yoo, E. J.; Park, S. H.; Lee, S. H.; Chang, S. Org. Lett. 2009, 11, 1155. |
| [30] | Chandna, N.; Kaur, F.; Kumar, S.; Jain, N. Green Chem. 2017, 19, 4268. |
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