含三氟甲基吡啶酰胺结构的N-氰基磺酰亚胺衍生物的合成及生物活性

doi:10.6023/cjoc202102017

有机化学 ›› 2021, Vol. 41 ›› Issue (9): 3633-3642.DOI: 10.6023/cjoc202102017 上一篇下一篇

研究论文

含三氟甲基吡啶酰胺结构的N-氰基磺酰亚胺衍生物的合成及生物活性

代阿丽, 张仁凤, 李传会, 余利娇, 王娅, 吴剑^*()

贵州大学绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与农业生物工程重点实验室贵阳 550025

收稿日期:2021-02-03 修回日期:2021-04-30 发布日期:2021-06-29
通讯作者: 吴剑
基金资助:
国家自然科学基金(21762012); 国家自然科学基金(32072445); 国家自然科学基金(21562012); 高等学校学科创新引智计划计划(D20023(111计划)); 高等学校学科创新引智计划计划(D20023(D20023)); 贵州省科技技术基金(黔科合[2017]1402); 贵州省科技技术基金(黔科合[2017]5788)

Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide

Ali Dai, Renfeng Zhang, Chuanhui Li, Lijiao Yu, Ya Wang, Jian Wu()

State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025

Received:2021-02-03 Revised:2021-04-30 Published:2021-06-29
Contact: Jian Wu
Supported by:
National Natural Science Foundation of China(21762012); National Natural Science Foundation of China(32072445); National Natural Science Foundation of China(21562012); Program of Introducing Talents to Chinese Universities (111 Program(D20023(D20023)); S &T Planning Project of Guizhou Province(黔科合[2017]1402); S &T Planning Project of Guizhou Province(黔科合[2017]5788)

文章分享

1. cjoc202102017辅助材料.pdf(1754KB)

摘要/Abstract

采用活性亚结构拼接法, 设计合成了系列新型含三氟甲基吡啶酰胺结构的N-氰基磺酰亚胺类衍生物, 其结构经¹H NMR、¹³C NMR、¹⁹F NMR和HRMS进行了表征. 评估了它们对柑橘溃疡病菌(Xanthomonas axonopodis pv. citri)、烟草青枯病菌(Ralstonia solanacearum)和水稻白叶枯病菌(Xanthomonas oryzae pv. oryzae)的杀菌活性及对小菜蛾(Plutella xylostella)的杀虫活性. 结果表明, 部分化合物表现出了良好的抗菌活性和中等的杀虫活性. 其中, 在200 mg/L质量浓度下, 3-氯-(2-(N-氰基-S-(3,4-二氟苄基)磺酰亚胺酰基)乙基)-5-(三氟甲基)吡啶酰胺(G10)对柑橘溃疡病菌、烟草青枯病菌和水稻白叶枯病菌的抑制率分别为67%、53%和48%, 3-氯-(2-(N-氰基-S-(2,5-二氟苄基)磺酰亚胺酰基)乙基)-5-(三氟甲基)吡啶酰胺(G17)对柑橘溃疡病菌的抗菌活性为69%, (2-(S-(2-溴-4-氟苄基)-N-氰基磺酰亚胺基)乙基)-3-氯-5-(三氟甲基)吡啶酰胺(G14)对水稻白叶枯病菌的抑制率为49%. 在100 mg/L时, (2-(S-(4-溴-2-氟苄基)-N-氰基磺酰亚胺基)乙基)-3-氯-5-(三氟甲基)吡啶酰胺(G1)、3-氯-(2-(N-氰基-S-(3-氟苄基)磺酰亚胺基)乙基)-5-(三氟甲基)吡啶酰胺(G7)、3-氯-(2-(N-氰基-S-(2,4-二氟苄基)磺酰亚胺酰基)乙基)-5-(三氟甲基)吡啶酰胺(G8)和G10也有中等的杀菌活性, 在测试浓度下, 部分化合物的活性略高于对照药剂或与之相当. 此外, 在500 mg/L时, 化合物G10和3-氯-(2-(N-氰基- S-(4-异丙基苄基)磺酰亚胺基)乙基)-5-(三氟甲基)吡啶酰胺(G11)对小菜蛾的致死率分别为77%和70%.

关键词: 三氟甲基吡啶, N-氰基磺酰亚胺, 合成, 杀菌活性, 杀虫活性

A series of novel N-cyano sulfonyimide derivatives containing trifluoromethyl pyridinamide were designed and synthesized by combination method of active substructure, and their structures were identified by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. Their antibacterial activity against Xanthomonas axonopodis pv. citri (Xac), Ralstonia solanacearum (R solanacearum), Xanthomonas oryzae pv. oryzae (Xoo) and insecticidal activity on Plutella xylostella (P. xylostella) were investigated. Some of the compounds were tested to display good antibacterial and moderate insecticidal activities. Among them, 3-chloro-N-(2-(N-cyano-S-(3,4-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G10) showed 67%, 53% and 48% activities against Xac, R. Solanacearum and Xoo at 200 mg/L, respectively. The antibacterial activity of 3-chloro-N- (2-(N-cyano-S-(2,5-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G17) against Xac was 69% and the inhibition rate of N-(2-(S-(2-bromo-4-fluorobenzyl)-N-cyanosulfonimidoyl)ethyl)-3-chloro-5-(trifluoromethyl)picolinamide (G14) on Xoo was 49%. N-(2-(S-(4-Bromo-2-fluorobenzyl)-N-cyanosulfonimidoyl)ethyl)-3-chloro-5-(trifluoromethyl)picolinamide (G1), 3-chloro-N-(2-(N-cyano-S-(3-fluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G7), 3-chloro- N-(2-(N-cyano-S-(2,4-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G8) and G10 also had moderate bactericidal activity at 100 mg/L, which are slightly higher than or comparable to that of the positive controls at the corresponding concentration. Moreover, compounds G10 and 3-chloro-N-(2-(N-cyano-S-(4-isopropylbenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G11) also showed moderate insecticidal activity against P. xvlostella of 77% and 70% at 500 mg/L.

Key words: trifluoromethylpyridine, N-cyano sulfonimide, synthesis, antibacterial activity, insecticidal activity

引用此文

代阿丽, 张仁凤, 李传会, 余利娇, 王娅, 吴剑. 含三氟甲基吡啶酰胺结构的N-氰基磺酰亚胺衍生物的合成及生物活性[J]. 有机化学, 2021, 41(9): 3633-3642.

Ali Dai, Renfeng Zhang, Chuanhui Li, Lijiao Yu, Ya Wang, Jian Wu. Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3633-3642.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 6

参考文献 42

[1]	Hu, Q.; Min, L.; Yang, X. Y.; Jin, S. X.; Zhang, L.; Li, Y. Y.; Ma, Y. Z.; Qi, X. W.; Li, D. Q.; Liu, H. B.; Zhu, L. F.; Zhang, X. L. Plant Physiol. 2018, 176, 1808. doi: 10.1104/pp.17.01628
[2]	Ferrarezi, J. H.; Dos Santos, J. A.; Sette, L. D.; Ferreira, H.; Sass, D. C. Afr. J. Biotechnol. 2019, 18, 713.
[3]	Chen, S.; Wang, C. Y.; Yang, J. Y.; Chen, B.; Wang, W. J.; Su, J.; Feng, A. Q.; Zeng, L. X.; Zhu, X. Y. Sci. Rep. 2020, 10, 12642. doi: 10.1038/s41598-020-69639-y
[4]	Chen, J. X.; Luo, Y. Q.; Wei, C. Q.; Wu, S. K.; Wu, R.; Wang, S. B.; Hu, D. Y.; Song, B. A. Pest Manage. Sci. 2020, 76, 3188. doi: 10.1002/ps.v76.9
[5]	Chen, X. J.; Li, L. C.; Wang, H. C.; Huang, Y. F.; Wang, M. S.; Zhang, C. Q. Plant Pathol. J. 2016, 15, 102. doi: 10.3923/ppj.2016.102.107
[6]	Isokar, S. S.; Bramhankar, S. B.; Das, A. K.; Thakur, K. D.; Pillai, Tini.; Dinkwar, G. T.; Kharat, V. M. Int. J. Chem. Stud. 2020, 8, 62.
[7]	Kemmitt, G.; Sparks, T. C.; Hunter, J. E.; Lorsbach, B. A.; Hanger, G.; Gast, R. E.; Bryant, R. J. J. Agric. Food Chem. 2018, 66, 10337.
[8]	Zhang, Y.; Pan, X. Y.; Duan, Y. B.; Zhu, X. F.; Ma, X. W.; Huang, T. T.; Gao, T. C.; Zhou, M. G. Australas. Plant Pathol. 2015, 44, 541. doi: 10.1007/s13313-015-0370-7
[9]	Dannenberg, C. A.; Fritze, L.; Krauskopf, F.; Bolm, C. Org. Biomol. Chem. 2017, 15, 1086. doi: 10.1039/c6ob02691e pmid: 28074951
[10]	Hu, W. M.; Teng, F.; Peng, H. B.; Yu, J. T.; Sun, S.; Cheng, J.; Shao, Y. Tetrahedron Lett. 2015, 56, 7056. doi: 10.1016/j.tetlet.2015.11.025
[11]	Hua, X. W.; Mao, W. T.; Fan, Z. J.; Ji, X. T.; Li, F. Y.; Zong, G. N.; Song, H. B.; Li, J. J.; Zhou, L. K.; Zhou, L. F.; Liang, X. W.; Wang, G. H.; Chen, X. Y. Aust. J. Chem. 2014, 67, 1491. doi: 10.1071/CH13701
[12]	Longhurst, C.; Babcock, J. M.; Denholm, I.; Gorman, K.; Thomas, J. D.; Sparks, T. C. Pest. Manage. Sci. 2013, 69, 809. doi: 10.1002/ps.2013.69.issue-7
[13]	Yu, H. B.; Qin, Z. F.; Dai, H.; Zhang, X.; Qin, X.; Wang, T. T.; Fang, J. X. ARKIVOC 2008, 16, 99.
[14]	Wang, Z. Y.; Guo, W.; Zhu, J. D. US 20190152932, 2019
	[Chem. Abstr. 2019, 164, 519677]
[15]	Hua, X. W.; Mao, W. T.; Fan, Z. J.; J, X. T.; Li, F. Y.; Zong, G. G.; Song, H. B.; Li, J. J.; Zhou, L. K.; Zhou, L. F.; Liang, X. W.; Wang, G. H.; Chen, X. Y. Aust. J. Chem. 2014, 67, 1491.
[16]	Mao, W. T.; Zong, G. N.; Fan, Z. J.; Li, F. Y.; Song, H. B.; Li, J. J.; Tatiana, K. A.; Inna, K.; Ksenia, L.; Yury, M. Y.; Nataliya, B. P. J. Struct. Chem. 2015, 34, 1428.
[17]	Pasteris, R. J.; Bereznak, J. F.; Chittaboina, S.WO 2018080859, 2018
	[Chem. Abstr. 2018, 168, 488871]
[18]	Hartmut, A.; Simon, D. R.; Stefan, L.; Hansjoerg, D.; Elmar, G.; Christopher, H.; Schmutzler, D.WO 2013124230, 2013
	[Chem. Abstr. 2013, 159, 399083]
[19]	Thorsten, O.; Dennis, F.; Christian, G.US 20140057926, 2014
	[Chem. Abstr. 2014, 160, 398991]
[20]	Christian, G.; Oost, Thorsten, O. US 20150239875A1, 2015
	[Chem. Abstr. 2015, 163, 363329]
[21]	Andreas, B.; Dirk, G.; Armin, H.; Joerg, P. H.; Bernhard, S.; Dieter, W.US 9708274, 2017
	[Chem. Abstr. 2017, 162, 137891]
[22]	Cumming, J. N.; Scott, J. D. US 20170260181, 2017
	[Chem. Abstr. 2017, 164, 406699]
[23]	Khan, T. A.; Scott, J. D.; Cumming, J. N. US 9422255, 2016
	[Chem. Abstr. 2016, 161, 535595]
[24]	Dai, A. L.; Guo, S. X.; Li, C. H.; Zhang, R. F.; Wu, J. Mod. Agrochem. 2020, 19, 21. (in Chinese).
	( 代阿丽, 郭声鑫, 李传会, 张仁凤, 吴剑, 现代农药, 2020, 19, 21.)
[25]	Cao, X. F.; Zhang, R. F. World Pestic. 2018, 40, 7. (in Chinese).
	( 曹晓峰, 张瑞峰, 世界农药, 2018, 40, 7.)
[26]	Deng, H. X. Zhejiang Chem. Ind. 2011, 42, 1. (in Chinese).
	( 邓红霞, 浙江化工, 2011, 42, 1.)
[27]	Luo, D. X.; Guo, S. X.; He, F.; Wang, H. Y.; Xu, F. Z.; Dai, A. L.; Zhang, R. F.; Wu, J. Bioorg. Med. Chem. Lett. 2020, 30, 126902. doi: 10.1016/j.bmcl.2019.126902
[28]	Hong, Y.; Dai, H.; Ye, L. Y.; Zhong, S. L.; Cao, X. F.; Shi, Y. J.; Li, C. J.; Shi, J.; Shi, L. Chin. J. Org. Chem. 2017, 37, 3006. (in Chinese). doi: 10.6023/cjoc201707022
	( 洪宇, 戴红, 叶林玉, 仲苏林, 曹熊飞, 石玉军, 李春建, 石健, 施磊, 有机化学, 2017, 37, 3006.)
[29]	Wang, Y. Y.; Xu, F. Z.; Luo, D. X.; Guo, S. X.; He, F.; Dai, A. L.; Song, B. A.; Wu, J. J. Agric. Food Chem. 2019, 67, 13344.
[30]	Xie, Y.; Chi, H. W.; Guan, A. Y.; Liu, C. L.; Ma, H. J.; Cui, D. L. J. Agric. Food Chem. 2014, 62, 12491.
[31]	Ji, X. X.; Li, J. J.; Meng, Z.; Zhang, S. A.; Dong, B.; Qiao, K. Plant Dis. 2019, 103, 1991. doi: 10.1094/PDIS-01-19-0143-RE
[32]	Chen, J. X.; Yi, C. F.; Wang, S. B.; Wu, S. K.; Li, S. Y.; Hu, D. Y.; Song, B. A. Bioorg. Med. Chem. Lett. 2019, 29, 1203. doi: 10.1016/j.bmcl.2019.03.017
[33]	Xu, F. Z.; Wang, Y. Y.; Luo, D. X.; Yu, G.; Guo, S. X.; Fu, H.; Zhao, Y. H.; Wu, J. RSC Adv. 2018, 8, 6306. doi: 10.1039/C8RA00161H
[34]	Xu, F. Z.; Wang, Y. Y.; Luo, D. X.; Yu, G.; Wu, Y. K.; Dai, A. L.; Zhao, Y. H.; Wu, J. ChemistrySelect 2018, 3, 2795. doi: 10.1002/slct.201800123
[35]	Guo, S. X.; He, F.; Dai, A. L.; Zhang, R. F.; Chen, S. H.; Wu, J. RSC Adv. 2020, 10, 35658. doi: 10.1039/D0RA07301F
[36]	Wu, J.; Hu, D. Y.; Yang, S. J. Guizhou Univ. (Nat. Sci.) 2006, 6, 622. (in Chinese).
	( 吴剑, 胡德禹杨松, 贵州大学学报(自然科学版), 2006, 6, 622.)
[37]	Christine, M. M. H.; Philip, L.; Julien, E.; Carsten, B. Adv. Synth. Catal. 2013, 355, 3363. doi: 10.1002/adsc.201300766
[38]	Shi, J.; Luo, N.; Ding, M. H.; Li, C. H.; Wan, S. R.; Li, P. J.; Li, J. H.; Bao, X. P. Chin. J. Org. Chem. 2021, 41, 738. (in Chinese). doi: 10.6023/cjoc202007068
	( 石军, 罗娜, 丁慕晗, 李传会, 万苏然, 李培甲, 李君荭, 鲍小平, 有机化学, 2021, 41, 738.)
[39]	Du, H.; Fan, Z. j.; Yang, L.; Bao, X. P. Chin. J. Org. Chem. 2018, 38, 531. (in Chinese). doi: 10.6023/cjoc201708051
	( 杜欢, 范治江, 杨岚, 鲍小平, 有机化学, 2018, 38, 531.)
[40]	Chen, Y.; Li, P.; Chen, M.; Su, S. J.; He, J.; Zhang, M. Liu, L. W.; Xue, W. Chin. J. Org. Chem. 2019, 39, 2813. (in Chinese). doi: 10.6023/cjoc201903048
	( 陈英, 李普, 陈梅, 苏时军, 贺军, 张敏, 柳立伟, 薛伟, 有机化学, 2019, 39, 2813.)
[41]	Shao, L. H.; Gan, Y. Y.; Hou, M.; Tao, S. L.; Zhang, L. Q.; Wang, Z. C.; Ouyang, G. P. Chin. J. Org. Chem. 2020, 40, 1975. (in Chinese). doi: 10.6023/cjoc202003013
	( 邵利辉, 甘宜远, 侯迷, 陶世林, 张丽琼, 王贞超, 欧阳贵平, 有机化学, 2020, 40, 1975.)
[42]	Luo, C. Y.; Ma, W. J.; Lv, L.; Pang, H. L.; Xiang, J. C.; Zhou, L. Q.; Yin, D. L.; Liu, J. Y. Chin. J. Org. Chem. 2020 40, 2963. (in Chinese). doi: 10.6023/cjoc202003025
	( 罗春艳, 马文静, 吕亮, 庞怀林, 相君成, 周丽琪, 尹笃林, 刘吉永, 有机化学, 2020 40, 2963.)

Compd.	Xac		R. solanacearum		Xoo
Compd.	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL
G1	49.26±3.73	48.55±2.35	43.21±4.11	41.72±1.57	47.41±4.49	39.09±4.56
G2	36.38±1.62	35.95±3.10	49.74±0.51	33.90±3.35	29.46±2.95	24.12±1.15
G3	33.97±1.39	31.07±0.99	46.76±2.76	34.90±3.68	17.58±3.95	0.63±1.51
G4	34.68±2.55	31.85±1.10	35.56±0.21	34.98±2.40	12.14±2.78	7.74±2.78
G5	40.06±2.44	34.75±2.41	33.28±3.76	32.32±0.95	16.64±0.75	3.98±0.75
G6	36.66±2.86	31.28±1.32	39.38±4.56	36.41±2.57	0.94±3.81	0.31±3.87
G7	51.88±4.59	42.60±1.12	51.01±3.30	38.73±2.33	15.70±4.16	1.62±5.00
G8	34.32±1.68	32.27±1.84	52.39±1.65	37.98±2.89	7.80±3.87	5.18±2.97
G9	36.02±1.48	31.78±0.45	45.06±2.25	24.20±4.88	14.55±3.25	10.36±3.54
G10	67.30±2.36	46.99±3.93	53.18±1.51	36.82±0.75	48.92±3.60	31.87±1.92
G11	59.94±2.42	46.19±4.16	36.52±1.80	35.14±2.55	19.94±4.73	5.86±4.26
G12	42.96±1.04	36.73±0.44	42.73±1.03	32.30±0.78	9.84±3.29	4.87±3.47
G13	40.62±1.03	36.23±2.66	29.09±2.40	27.65±3.04	25.54±4.29	24.96±1.47
G14	35.31±2.45	23.21±1.75	31.58±2.36	29.99±0.70	49.55±2.40	12.72±3.20
G15	35.78±2.25	32.77±3.36	45.59±3.21	28.75±1.99	28.57±4.05	24.39±2.36
G16	49.04±2.26	27.25±3.23	42.36±2.69	32.60±0.15	17.63±4.31	4.55±2.71
G17	69.14±4.77	38.36±1.38	45.70±3.80	19.90±0.52	22.45±1.41	19.31±3.60
G18	32.91±1.45	32.34±2.16	37.69±4.10	26.52±2.49	22.08±1.45	27.26±0.38
G19	47.56±1.65	30.36±3.61	35.51±1.39	26.11±4.35	38.88±1.91	36.42±3.56
G20	48.90±2.72	32.84±0.93	43.52±1.68	31.85±0.17	23.39±3.70	14.91±4.72
噻唑锌	75.30±1.62	58.21±2.34	52.30±1.15	35.90±2.65	68.23±1.28	50.36±3.17
中生菌素	52.32±2.38	43.31±1.68	51.20±3.02	33.52±2.19	65.35±3.12	46.53±2.82

Compd.	Xac		R. solanacearum		Xoo
Compd.	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL
G1	49.26±3.73	48.55±2.35	43.21±4.11	41.72±1.57	47.41±4.49	39.09±4.56
G2	36.38±1.62	35.95±3.10	49.74±0.51	33.90±3.35	29.46±2.95	24.12±1.15
G3	33.97±1.39	31.07±0.99	46.76±2.76	34.90±3.68	17.58±3.95	0.63±1.51
G4	34.68±2.55	31.85±1.10	35.56±0.21	34.98±2.40	12.14±2.78	7.74±2.78
G5	40.06±2.44	34.75±2.41	33.28±3.76	32.32±0.95	16.64±0.75	3.98±0.75
G6	36.66±2.86	31.28±1.32	39.38±4.56	36.41±2.57	0.94±3.81	0.31±3.87
G7	51.88±4.59	42.60±1.12	51.01±3.30	38.73±2.33	15.70±4.16	1.62±5.00
G8	34.32±1.68	32.27±1.84	52.39±1.65	37.98±2.89	7.80±3.87	5.18±2.97
G9	36.02±1.48	31.78±0.45	45.06±2.25	24.20±4.88	14.55±3.25	10.36±3.54
G10	67.30±2.36	46.99±3.93	53.18±1.51	36.82±0.75	48.92±3.60	31.87±1.92
G11	59.94±2.42	46.19±4.16	36.52±1.80	35.14±2.55	19.94±4.73	5.86±4.26
G12	42.96±1.04	36.73±0.44	42.73±1.03	32.30±0.78	9.84±3.29	4.87±3.47
G13	40.62±1.03	36.23±2.66	29.09±2.40	27.65±3.04	25.54±4.29	24.96±1.47
G14	35.31±2.45	23.21±1.75	31.58±2.36	29.99±0.70	49.55±2.40	12.72±3.20
G15	35.78±2.25	32.77±3.36	45.59±3.21	28.75±1.99	28.57±4.05	24.39±2.36
G16	49.04±2.26	27.25±3.23	42.36±2.69	32.60±0.15	17.63±4.31	4.55±2.71
G17	69.14±4.77	38.36±1.38	45.70±3.80	19.90±0.52	22.45±1.41	19.31±3.60
G18	32.91±1.45	32.34±2.16	37.69±4.10	26.52±2.49	22.08±1.45	27.26±0.38
G19	47.56±1.65	30.36±3.61	35.51±1.39	26.11±4.35	38.88±1.91	36.42±3.56
G20	48.90±2.72	32.84±0.93	43.52±1.68	31.85±0.17	23.39±3.70	14.91±4.72
噻唑锌	75.30±1.62	58.21±2.34	52.30±1.15	35.90±2.65	68.23±1.28	50.36±3.17
中生菌素	52.32±2.38	43.31±1.68	51.20±3.02	33.52±2.19	65.35±3.12	46.53±2.82

Compd.	Activity/%	Compd.	Activity/%
G1	30±1.0	G12	57±2.5
G2	60±1.0	G13	57±1.5
G3	50±1.0	G14	40±1.0
G4	60±2.1	G15	30±1.0
G5	63±0.6	G16	30±1.0
G6	33±1.2	G17	53±1.5
G7	33±1.0	G18	40±1.0
G8	50±1.2	G19	67±0.6
G9	47±1.2	G20	47±1.2
G10	77±1.5	毒死蜱	100±0
G11	70±1.7	阿维菌素	100±0

Compd.	Activity/%	Compd.	Activity/%
G1	30±1.0	G12	57±2.5
G2	60±1.0	G13	57±1.5
G3	50±1.0	G14	40±1.0
G4	60±2.1	G15	30±1.0
G5	63±0.6	G16	30±1.0
G6	33±1.2	G17	53±1.5
G7	33±1.0	G18	40±1.0
G8	50±1.2	G19	67±0.6
G9	47±1.2	G20	47±1.2
G10	77±1.5	毒死蜱	100±0
G11	70±1.7	阿维菌素	100±0

含三氟甲基吡啶酰胺结构的N-氰基磺酰亚胺衍生物的合成及生物活性

Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 6

参考文献 42

相关文章 15

编辑推荐

相关统计

本文评价

[1]	冯康博, 陈炯, 古双喜, 王海峰, 陈芬儿. 全连续流反应技术在药物合成中的新进展(2019~2022)[J]. 有机化学, 2024, 44(2): 378-397.
[2]	李鹏辉, 谢青洋, 万福贤, 张元红, 姜林. 含环丙基的新型取代嘧啶-5-甲酰胺的合成及杀菌活性研究[J]. 有机化学, 2024, 44(2): 650-656.
[3]	邹发凯, 王能中, 姚辉, 王慧, 刘明国, 黄年玉. 1β-/3R-芳基硫代糖的区域与立体选择性合成[J]. 有机化学, 2024, 44(2): 593-604.
[4]	李路瑶, 贺忠文, 张振国, 贾振华, 罗德平. 三芳基碳正离子在有机合成中的应用[J]. 有机化学, 2024, 44(2): 421-437.
[5]	梅青刚, 李清寒. 可见光促进C(3)(杂)芳硫基吲哚化合物的合成研究进展[J]. 有机化学, 2024, 44(2): 398-408.
[6]	赵茜帆, 陈永正, 张世明. 碳基非金属催化剂在有机合成领域的应用及机理研究[J]. 有机化学, 2024, 44(1): 137-147.
[7]	陈珊, 陈志林, 胡琼, 蒙艳双, 黄悦, 陶萍芳, 卢丽如, 黄国保. 含双硫脲基团分子钳在非极性溶剂中识别中性分子[J]. 有机化学, 2024, 44(1): 277-281.
[8]	王化坤, 任晓龙, 宣宜宁. 卤盐催化的α,β-环氧羧酸酯与异氰酸酯[3＋2]环加成反应研究[J]. 有机化学, 2024, 44(1): 251-258.
[9]	金玉坤, 任保轶, 梁福顺. 可见光介导的三氟甲基的选择性C－F键断裂及其在偕二氟类化合物合成中的应用[J]. 有机化学, 2024, 44(1): 85-110.
[10]	马翠云, 罗海澜, 张福华, 郭丹, 陈树兴, 王飞. 3-Pyrrolyl BODIPY的绿色生物合成、光物理性质及应用研究[J]. 有机化学, 2024, 44(1): 216-223.
[11]	王博珍, 张婕, 粘春惠, 金茗茗, 孔苗苗, 李物兰, 何文斐, 吴建章. 含有3,4-二氯苯基的酰胺类化合物的合成及抗肿瘤活性研究[J]. 有机化学, 2024, 44(1): 232-241.
[12]	杨维清, 葛宴兵, 陈元元, 刘萍, 付海燕, 马梦林. 1,8-萘酰亚胺衍生物的设计、合成及其对半胱氨酸的识别研究[J]. 有机化学, 2024, 44(1): 180-194.
[13]	于士航, 刘嘉威, 安碧玉, 边庆花, 王敏, 钟江春. 黑腹尼虎天牛接触性信息素的不对称合成[J]. 有机化学, 2024, 44(1): 301-308.
[14]	李阳, 袁锦鼎, 赵頔. 低共熔溶剂1,3-二甲基脲/L-(+)-酒石酸中(E)-2-苯乙烯基喹啉-3-羧酸类衍生物的绿色合成[J]. 有机化学, 2023, 43(9): 3268-3276.
[15]	岁丹丹, 岑南楠, 龚若蕖, 陈阳, 陈文博. 无支持电解质条件下连续流电化学合成三氟甲基化氧化吲哚[J]. 有机化学, 2023, 43(9): 3239-3245.