含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究

doi:10.6023/cjoc202008006

有机化学 ›› 2021, Vol. 41 ›› Issue (2): 708-718.DOI: 10.6023/cjoc202008006 上一篇下一篇

研究论文

含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究

贺军¹, 唐雪梅¹, 周清¹, 彭峰¹, 刘婷婷¹, 柳立伟¹, 贺鸣¹, 谢承卫¹, 薛伟¹^,^*()

1 贵州大学精细化工研究开发中心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生物工程重点实验室贵阳 550025

收稿日期:2020-08-07 修回日期:2020-09-04 发布日期:2020-10-12
通讯作者: 薛伟
作者简介:
* Corresponding author. E-mail: wxue@gzu.edu.cn
基金资助:
国家自然科学基金(21867003); 贵州省自然科学基金(20192452); 贵州省自然科学基金(20191105); 贵州省自然科学基金(20171028)

Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety

Jun He¹, Xuemei Tang¹, Qing Zhou¹, Feng Peng¹, Tingting Liu¹, Liwei Liu¹, Ming He¹, Chengwei Xie¹, Wei Xue¹^,^*()

1 Laboratory of Green Pesticide and Bioengineering of Ministry of Education, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received:2020-08-07 Revised:2020-09-04 Published:2020-10-12
Contact: Wei Xue
Supported by:
the National Natural Science Foundation of China(21867003); the Natural Science Foundation of Guizhou Province(20192452); the Natural Science Foundation of Guizhou Province(20191105); the Natural Science Foundation of Guizhou Province(20171028)

文章分享

1. cjoc202008006辅助材料.pdf(3517KB)

摘要/Abstract

以杨梅苷为原料, 通过活性拼接, 设计并合成一系列含喹唑啉硫醚的杨梅素衍生物, 其结构通过¹H NMR、¹³C NMR、¹⁹F NMR和HRMS进行确证. 生物活性测试结果表明, 该类化合物对水稻白叶枯病菌(X. Oryzae)、柑橘溃疡病菌(X. Citri)和烟草青枯病菌(R. Solanacearum)表现出一定的抑制活性. 其中, 5,7-二甲氧基-3-(3-((6-溴喹唑啉-4-基)硫基)丙氧基)-2-(3,4,5-三甲氧基苯基)-4H-色烯-4-酮(A₁₅)对水稻白叶枯病菌的EC₅₀值为13.9 μg/mL, 优于对照药叶枯唑(88.9 μg/mL)和噻菌铜(68.1 μg/mL); 5,7-二甲氧基-3-(4-((6-氯喹唑啉-4-基)硫基)丁氧基)-2-(3,4,5-三甲氧基苯基)-4H-色烯-4-酮(A₃)、5,7-二甲氧基-3-(3-((6-氯喹唑啉-4-基)硫基)丙氧基)-2-(3,4,5-三甲氧基苯基)-4H-色烯-4-酮(A₁₄)、5,7-二甲氧基- 3-(3-((6-溴喹唑啉-4-基)硫基)丙氧基)-2-(3,4,5-三甲氧基苯基)-4H-色烯-4-酮(A₁₅)和5,7-二甲氧基-3-(3-((6-氟喹唑啉-4-基)硫基)丙氧基)-2-(3,4,5-三甲氧基苯基)-4H-色烯-4-酮(A₁₆)对烟草青枯病菌的EC₅₀值分别为1.1, 14.0, 11.9和7.5 μg/mL, 优于对照药叶枯唑(38.5 μg/mL)和噻菌铜(184.8 μg/mL). 活体实验结果表明, 化合物A₁₅对水稻白叶枯病菌的具有良好治疗活性和保护活性. 通过扫描电镜成像初步探讨了目标化合物A₃对烟草青枯病菌和A₁₅对水稻白叶枯病菌的抑菌作用机制.

关键词: 杨梅素衍生物, 喹唑啉硫醚, 生物活性, 活体实验, 扫描电镜

A series of myricetin derivatives containing quinazoline thioether moiety were designed and synthesized using myricetrin as the starting material through active splicing strategy. All target compounds were characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. Their biological activities were evaluated. The results of biological activities showed that these compounds exhibited certain inhibitory activities against X. oryzae, X. citri and R. solanacearum. Among them, 3-(3-((6-bro- moquinazolin-4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₁₅) displayed appreciable inhibitory effect against X. oryzae with a half maximal effective concentration (EC₅₀) values of 13.9 μg/mL, which was better than those of the control drugs of bismerthiazol (88.9 μg/mL) and thiodiazole-copper (68.1 μg/mL). The EC₅₀ values of 3-(4- ((6-chloroquinazolin-4-yl)thio)butoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₃), 3-(3-((6-chloro- quinazolin-4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₁₄), 3-(3-((6-chloroquinazolin- 4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₁₅) and 3-(3-((6-fluoroquinazolin-4-yl)- thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₁₆) against Ralstonia solanacearum were 1.1, 14.0, 11.9 and 7.5 μg/mL, respectively, which were superior to the control drugs of bismerthiazol (38.5 μg/mL) and thio-diazole-copper (184.8 μg/mL). The results of in vivo experiments showed that compound A₁₅ has good curative and protective activities against X. oryzae. The possible antibacterial mechanisms of target compound A₃ against R. solanacearum and A₁₅ against X. oryzae were preliminarily discussed base on scanning electron microscope analyses.

Key words: myricetin derivative, quinazoline thioether, biological activity, in vivo experiment, scanning electron microscope

引用此文

贺军, 唐雪梅, 周清, 彭峰, 刘婷婷, 柳立伟, 贺鸣, 谢承卫, 薛伟. 含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究[J]. 有机化学, 2021, 41(2): 708-718.

Jun He, Xuemei Tang, Qing Zhou, Feng Peng, Tingting Liu, Liwei Liu, Ming He, Chengwei Xie, Wei Xue. Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 708-718.

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

分享此文

图/表 10

参考文献 30

[1]	Fan, Z.J.; Shi, J., Luo, N.; Ding, M.H.; Bao, X.P. J. Agric. Food Chem. 2019, 67, 11598. doi: 10.1021/acs.jafc.9b04733
[2]	Jiang, S.C.; Tang, X.; Chen, M.; He, J.; Su, S.J.; Liu, L.W.; Xue, W. Pest Manage. Sci. 2019, 76, 853. doi: 10.1002/ps.v76.3
[3]	Tang, X.; Zhang, C.; Chen, M.; Xue, Y.N.; Liu, T.T.; Xue, W. New J. Chem. 2020, 44, 2374. doi: 10.1039/C9NJ05867B
[4]	Mo, F.; Ma, J.; Yang, X.; Zhang, P.; Li, Q.; Zhang, J. Phytomedicine 2020, 153223.
[5]	Yu, M.S.; Lee, J.; Lee, J.M.; Kim, Y.; Chin, Y.W.; Jee, J.G.; Jeong, Y.J. Bioorg. Med. Chem. Lett. 2012, 22, 4049.
[6]	Sun, F.; Zheng, X.Y.; Ye, J.; Wu, T.T.; Wang, J.L.; Chen, W. Nutr. Cancer 2012, 64, 599. doi: 10.1080/01635581.2012.665564
[7]	Afroze, N.; Pramodh, S.; Hussain, A.; Waleed, M.; Vakharia, K. 3 Biotech 2020, 10, 211. doi: 10.1007/s13205-020-02207-3 pmid: 32351869
[8]	Wang, S.J.; Tong, Y.; Lu, S.; Yang, R.; Liao, X.; Xu, Y.F.; Li, X. Planta Med. 2010, 76, 1492. doi: 10.1055/s-0030-1249780
[9]	Jiang, M.; Zhu, M.; Wang, L.; Yu, S. Biomed. Pharmacother. 2019, 120, 109506. doi: 10.1016/j.biopha.2019.109506
[10]	Guitard, R.; Paul, J.F.; Véronique, N.R.; Aubry, J.M. Food Chem. 2016, 213.
[11]	Jiang, S.C.; Su, S.J.; Chen, M.; Peng, F.; Zhou, Q.; Liu, L.W.; Xue, W. J. Agric. Food Chem. 2020, 68, 5641. doi: 10.1021/acs.jafc.0c01652
[12]	Li, P. ; Chen, Y. ; Xia, R.J. ; Guo, T. ; Zhang, M. ; Jiang, S.C. ; Tang, X. ; He, M. ; Xue, W. Chem. J. Chin. Univ. 2019, 40, 909. (in Chinese)
	李普, 陈英, 夏榕娇, 郭涛, 张敏, 蒋仕春, 汤旭, 贺鸣, 薛伟, 高学校化学学报, 2019, 40, 909.).
[13]	Liu, H.B. ; Lv, P. ; Pan, N.N. ; Ai, L.M. ; Liu, Y.X. Chem. J. Chin. Univ. 2014, 35, 981. (in Chinese)
	刘海彬, 吕萍, 潘宁宁, 艾丽梅, 刘永祥, 高学校化学学报, 2014, 35, 981.).
[14]	Xu, Y.Y. M.S. Thesis, Suzhou University, Suzhou, 2014. (in Chinese)
	许芸芸, 硕士论文, 苏州大学, 苏州, 2014. ).
[15]	Zhang, G.Q. ; Guo, Q.Q. ; Zhao, T.Y. ; Wang, M. ; Xing, L.N. Chin. J. Synth. Chem. 2020, 28, 491. (in Chinese)
	张贵强, 郭晴晴, 易君明, 赵廷渊, 王梅, 邢林娜, 合成化学, 2020, 28, 491.).
[16]	Dos, R.; Sharon, V.; Ribeiro, N.S.; Rocha, D.A.; Fortes, I.S.; Silva, T.D.; Andrade, S.F.; Macedo, A.J. Chem. Biol. Drug Des. 2020.
[17]	Wan, Z.H. M.S. Thesis, Guizhou University, Guiyang, 2015 (in Chinese)
	万治华, 硕士论文, 贵州大学, 贵阳, 2015. ).
[18]	Sun, H.Y. ; Sun, H.S. ; Liu, M.Z. ; Huang, W. ; Yang, G.F. Chin. J. Org. Chem. 2018, 38, 2067. (in Chinese) doi: 10.6023/cjoc201801001 pmid: 4FA21444-EA59-40C1-AD40-801153E03F2D
	孙海燕, 孙宏顺, 刘明珍, 黄伟, 杨光富, 有机化学, 2018, 38,2067. ). doi: 10.6023/cjoc201801001 pmid: 4FA21444-EA59-40C1-AD40-801153E03F2D
[19]	Wu, J.; Bai, S.; Yue, M.; Luo, L.J.; Shi, Q.C.; Ma, J.; Du, X.L.; Kang, S.H.; Hu, D.Y.; Yang, S. Chem. Pap. 2014, 68, 969.
[20]	Gao, X.W. ; Cai, X.J. ; Yan, K. ; Gao, L.L. ; Wang, H.Y. ; Chen, Z. ; Song, B.A. Chin. J. Org. Chem. 2008, 28, 1785. (in Chinese)
	高兴文, 蔡学建, 严凯, 高丽丽, 王和英, 陈卓, 宋宝安, 有机化学, 2008, 28, 1785.).
[21]	Li, Q. M.S. Thesis, Guizhou University, Guiyang, 2018 (in Chinese)
	李琴, 硕士论文, 贵州大学, 贵阳, 2018. ).
[22]	Liu, J.H. ; Liu, Y. ; Jian, J.Y. ; Bao, X.P. Chin. J. Org. Chem. 2013, 33, 370. (in Chinese) doi: 10.6023/cjoc201209023 pmid: 11C482BE-3826-4983-A1EE-9E2D78F6A53D
	刘军虎, 刘勇, 蹇军友, 鲍小平, 有机化学, 2013, 33, 370.). doi: 10.6023/cjoc201209023 pmid: 11C482BE-3826-4983-A1EE-9E2D78F6A53D
[23]	Zhang, C.R. ; Wang, L. ; Ge, Y.L. ; Ju, X.L. Chin. J. Org. Chem. 2007, 27, 1432. (in Chinese) pmid: 3EE5FFF9-1017-4055-94E0-F766AF5A8D30
	张成仁, 王柳, 葛燕丽, 巨修练, 有机化学, 2007, 27, 1432.). pmid: 3EE5FFF9-1017-4055-94E0-F766AF5A8D30
[24]	Yang, Y. ; Ma, Y.N. ; Huang, T. ; Xie, W. ; Zhang, X. ; Huang, G.S. ; Liu, X.D. Chin. J. Org. Chem. 2018, 38, 2143. (in Chinese) doi: 10.6023/cjoc201801024 pmid: 2F15FB54-4D6B-4FD4-874B-4E042BF95257
	杨锐, 马艳妮, 黄婷, 解伟, 张霞, 黄国双, 刘小东, 有机化学, 2018, 38, 2143.). doi: 10.6023/cjoc201801024 pmid: 2F15FB54-4D6B-4FD4-874B-4E042BF95257
[25]	Xue, W.; Song, B.A.; Zhao, H.J; Qi, X.B.; Huang, Y.J.; Liu, X.H. Eur. J. Med. Chem. 2015, 97, 155. doi: 10.1016/j.ejmech.2015.04.063
[26]	Chen, Y.; Li, P.; Su, S.J.; Chen, M.; He, J.; Liu, L.W.; Xue, W. RSC Adv. 2019, 9, 23045. doi: 10.1039/C9RA05139B
[27]	Long, C.W. M.S. Thesis, Guizhou University, Guiyang, 2015 (in Chinese)
	龙承文, 硕士论文, 贵州大学, 贵阳, 2015. ).
[28]	Zhang, C. ; Jiang, S.C. ; Chen, Y. ; Guo, T. ; Xia, R.J. ; Tang, X. ; Chen, L.J. ; He, M. ; Xue, W. Chin. J. Org. Chem. 2019, 39, 1160. (in Chinese) doi: 10.6023/cjoc201809040 pmid: DECEC00F-5C46-4CBC-9383-F2F20CA3E870
	张橙, 蒋仕春, 陈英, 郭涛, 夏榕娇, 汤旭, 陈丽娟, 贺鸣, 薛伟, 有机化学, 2019, 39, 1160.). doi: 10.6023/cjoc201809040 pmid: DECEC00F-5C46-4CBC-9383-F2F20CA3E870
[29]	Wang, L.; Zhou, X.; Lu, H.; Mu, X.F.; Jin, L.H. Molecules 2020, 25, 1488. doi: 10.3390/molecules25071488
[30]	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 pmid: CFF8992F-E3F2-45B7-9EE9-7CCC16E0A1D0
	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.). doi: 10.6023/cjoc201903048 pmid: CFF8992F-E3F2-45B7-9EE9-7CCC16E0A1D0

Compd.	R	n	X. oryzae				R. solanacearum
Compd.	R	n	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL
A₁	6-Me	4	22.2±8.1	20.0±4.2	15.6±2.9	14.9±1.3	—	—
A₂	8-Me	4	32.7±0.1	16.6±3.5	10.1±5.3	6.7±2.9	21.5±1.6	13.3±0.5
A₃	Cl	4	59.9±4.6	27.3±0.3	11.3±2.7	—	88.4±5.5	83.8±4.4
A₄	6-Br	4	64.2±5.2	42.0±0.6	—	—	86.8±3.5	55.5±4.5
A₅	6-F	4	42.2±6.4	35.5±1.1	11.2±3.8	9.6±1.9	66.9±3.8	44.1±2.4
A₆	7-Cl	4	30.9±4.9	28.4±5.2	8.5±3.4	6.7±1.0	65.8±3.4	57.1±3.9
A₇	6-I	4	28.7±3.9	26.5±2.6	—	—	80.7±2.9	63.0±3.5
A₈	6-Cl-8-Me	4	42.6±3.4	36.6±0.9	30.0 ± 5.0	23.3±1.7	70.4±1.3	77.3±6.8
A₉	7-F	4	50.4±2.0	30.1±1.3	16.6±0.8	22.2±3.4	70.8±4.0	59.1±3.9
A₁₀	6,7-(OMe)₂	4	41.4±2.4	28.1±2.0	8.8±2.2	5.3±1.6	40.7±6.1	27.1±7.0
A₁₁	7,8-Me₂	4	40.4±4.4	34.2±5.5	—	—	22.2±5.4	16.9±6.5
A₁₂	6-Me	3	23.7±4.5	23.4±1.7	12.5±1.2	12.7±2.3	12.1±5.4	—
A₁₃	8-Me	3	26.8±2.8	23.2±7.4	11.5±2.9	4.4±1.8	8.7±4.3	—
A₁₄	6-Cl	3	44.6±2.5	29.8±2.9	33.1±2.2	13.3±2.2	77.6±1.3	71.3±3.8
A₁₅	6-Br	3	86.1±5.1	71.4±4.5	58.0±2.3	12.1±1.1	99.1±3.0	76.2±3.6
A₁₆	6-F	3	44.9±3.2	40.6±4.7	—	—	73.1±2.7	66.0±5.2
A₁₇	7-Cl	3	31.2±2.8	28.4±3.2	19.3±1.2	15.2±0.6	19.7±3.5	12.7±1.6
A₁₈	6-I	3	62.8±3.8	39.9±5.6	56.2±3.4	28.3±0.9	35.1±5.2	19.1±1.2
A₁₉	6-Cl-8-Me	3	42.7±3.4	36.0±7.4	21.1±5.0	19.0±2.2	50.8±1.6	42.8±0.7
A₂₀	7-F	3	41.4±4.4	29.2±0.8	23.8±1.6	10.6±4.2	63.3±8.7	39.1±4.5
A₂₁	6,7-(OMe)₂	3	34.1±2.8	24.5±0.8	12.1±3.0	—	12.1±4.1	6.6±2.9
A₂₂	7,8-Me₂	3	58.0±2.3	47.7±0.4	18.3±5.3	11.6±6.9	38.5±2.9	33.4±6.7
中间体1	—	—	35.5±1.6	18.3±1.9	18.9±4.0	9.3±2.8	40.8±2.0	14.0±1.3
杨梅素	—	—	30.3±5.3	10.6±0.5	11.0±3.5	—	9.3±4.5	5.2±3.0
杨梅苷	—	—	10.9±3.9	8.9±5.1	—	—	20.9±2.0	7.7±4.8
叶枯唑^b	—	—	55.1±1.82	39.0±1.8	51.4±2.0	19.2±2.0	59.5±5.7	51.7±0.2
噻菌铜^b	—	—	62.2±4.8	36.1±4.4	63.3±0.6	18.5±6.0	38.4±3.8	20.9±1.6

Compd.	R	n	X. oryzae				R. solanacearum
Compd.	R	n	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL
A₁	6-Me	4	22.2±8.1	20.0±4.2	15.6±2.9	14.9±1.3	—	—
A₂	8-Me	4	32.7±0.1	16.6±3.5	10.1±5.3	6.7±2.9	21.5±1.6	13.3±0.5
A₃	Cl	4	59.9±4.6	27.3±0.3	11.3±2.7	—	88.4±5.5	83.8±4.4
A₄	6-Br	4	64.2±5.2	42.0±0.6	—	—	86.8±3.5	55.5±4.5
A₅	6-F	4	42.2±6.4	35.5±1.1	11.2±3.8	9.6±1.9	66.9±3.8	44.1±2.4
A₆	7-Cl	4	30.9±4.9	28.4±5.2	8.5±3.4	6.7±1.0	65.8±3.4	57.1±3.9
A₇	6-I	4	28.7±3.9	26.5±2.6	—	—	80.7±2.9	63.0±3.5
A₈	6-Cl-8-Me	4	42.6±3.4	36.6±0.9	30.0 ± 5.0	23.3±1.7	70.4±1.3	77.3±6.8
A₉	7-F	4	50.4±2.0	30.1±1.3	16.6±0.8	22.2±3.4	70.8±4.0	59.1±3.9
A₁₀	6,7-(OMe)₂	4	41.4±2.4	28.1±2.0	8.8±2.2	5.3±1.6	40.7±6.1	27.1±7.0
A₁₁	7,8-Me₂	4	40.4±4.4	34.2±5.5	—	—	22.2±5.4	16.9±6.5
A₁₂	6-Me	3	23.7±4.5	23.4±1.7	12.5±1.2	12.7±2.3	12.1±5.4	—
A₁₃	8-Me	3	26.8±2.8	23.2±7.4	11.5±2.9	4.4±1.8	8.7±4.3	—
A₁₄	6-Cl	3	44.6±2.5	29.8±2.9	33.1±2.2	13.3±2.2	77.6±1.3	71.3±3.8
A₁₅	6-Br	3	86.1±5.1	71.4±4.5	58.0±2.3	12.1±1.1	99.1±3.0	76.2±3.6
A₁₆	6-F	3	44.9±3.2	40.6±4.7	—	—	73.1±2.7	66.0±5.2
A₁₇	7-Cl	3	31.2±2.8	28.4±3.2	19.3±1.2	15.2±0.6	19.7±3.5	12.7±1.6
A₁₈	6-I	3	62.8±3.8	39.9±5.6	56.2±3.4	28.3±0.9	35.1±5.2	19.1±1.2
A₁₉	6-Cl-8-Me	3	42.7±3.4	36.0±7.4	21.1±5.0	19.0±2.2	50.8±1.6	42.8±0.7
A₂₀	7-F	3	41.4±4.4	29.2±0.8	23.8±1.6	10.6±4.2	63.3±8.7	39.1±4.5
A₂₁	6,7-(OMe)₂	3	34.1±2.8	24.5±0.8	12.1±3.0	—	12.1±4.1	6.6±2.9
A₂₂	7,8-Me₂	3	58.0±2.3	47.7±0.4	18.3±5.3	11.6±6.9	38.5±2.9	33.4±6.7
中间体1	—	—	35.5±1.6	18.3±1.9	18.9±4.0	9.3±2.8	40.8±2.0	14.0±1.3
杨梅素	—	—	30.3±5.3	10.6±0.5	11.0±3.5	—	9.3±4.5	5.2±3.0
杨梅苷	—	—	10.9±3.9	8.9±5.1	—	—	20.9±2.0	7.7±4.8
叶枯唑^b	—	—	55.1±1.82	39.0±1.8	51.4±2.0	19.2±2.0	59.5±5.7	51.7±0.2
噻菌铜^b	—	—	62.2±4.8	36.1±4.4	63.3±0.6	18.5±6.0	38.4±3.8	20.9±1.6

Compd.	n	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
A₄	4	6-Br	y=1.8096x+1.6782	0.9627	68.5
A₁₅	3	6-Br	y=1.1947x+3.6346	0.9934	13.9
A₁₈	3	6-I	y=1.3339x+2.4922	0.9715	75.9
噻菌铜^a	—	—	y=1.8570x+1.5964	0.9910	68.1
叶枯唑^a	—	—	y=1.2079x+2.6426	0.9844	88.9

Compd.	n	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
A₄	4	6-Br	y=1.8096x+1.6782	0.9627	68.5
A₁₅	3	6-Br	y=1.1947x+3.6346	0.9934	13.9
A₁₈	3	6-I	y=1.3339x+2.4922	0.9715	75.9
噻菌铜^a	—	—	y=1.8570x+1.5964	0.9910	68.1
叶枯唑^a	—	—	y=1.2079x+2.6426	0.9844	88.9

Compd.	n	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
A₃	4	6-Cl	y=0.593x+4.9827	0.9921	1.1
A₄	4	6-Br	y=1.8966x+2.1798	0.9632	30.7
A₅	4	6-F	y=0.8597x+3.5656	0.9585	46.6
A₆	4	7-Cl	y=0.5752x+4.2419	0.9636	20.1
A₇	4	6-I	y=1.4886x+2.9695	0.9507	23.1
A₈	4	6-Cl-8-Me	y=1.4015x+3.064	0.9633	24.1
A₉	4	7-F	y=1.3577x+2.8057	0.9934	41.3
A₁₄	3	6-Cl	y=0.9359x+3.9275	0.9617	14.0
A₁₅	3	6-Br	y=1.7487x+3.0242	0.9766	11.9
A₁₆	3	6-F	y=0.8035x+4.2979	0.9904	7.5
A₂₀	3	6-Cl-8-Me	y=0.538x+3.9015	0.9582	110.1

含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究

Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 10

参考文献 30

相关文章 15

编辑推荐

相关统计

本文评价

Compd.	n	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
噻菌铜^a	—	—	y=0.6931x+3.4289	0.9773	184.8
叶枯唑^a	—	—	y=0.8701x+4.0372	0.9753	38.5

Treatment	Morbidity/ %	Disease index/ %	Control efficiency/ %
A₁₅	100	44.1	49.4
叶枯唑^a	100	47.6	45.3
噻菌铜^a	100	56.8	34.8
CK^b	100	87.0	—

Treatment	Morbidity/ %	Disease index/ %	Control efficiency/ %
A₁₅	100	45.9	47.2
叶枯唑^a	100	45.5	47.7
噻菌铜^a	100	56.5	35.1
CK^b	100	87.0	—

[1]	光明甲, 姜硕, 朱宝玉, 张如松, 王鲲鹏, 王明慧, 许良忠. 新型吡咯-2-甲酸及其衍生物的设计、合成和杀虫、杀螨活性[J]. 有机化学, 2023, 43(8): 2895-2904.
[2]	何金燕, 田富云, 吴青青, 郑月明, 陈玉婷, 许海燕, 金正盛, 詹丽, 程新强, 顾跃玲, 高召兵, 赵桂龙. 基于[3.3.3]螺桨烷的电压门控钙离子通道α2δ亚基配体的合成和生物活性研究[J]. 有机化学, 2023, 43(6): 2226-2238.
[3]	孙洋, 王杨, 张紫婵, 钱烨, 骆桂成, 周贝贝, 缪丽沙, 陈雨蝶, 戴红, 徐宝琳, 吴正光. 新型含1,3,4-噁二唑基团的吡唑肟衍生物的合成与生物活性[J]. 有机化学, 2023, 43(4): 1584-1590.
[4]	王启帆, 张源泉, 幸丽, 周远香, 龚晨裕, 何帮灿, 张念, 吴拥军, 薛伟. 含1,2,4-三唑并[3,4-b]-1,3,4-噻二唑杨梅素衍生物的设计、合成及生物活性研究[J]. 有机化学, 2023, 43(4): 1525-1536.
[5]	雍灿, 李芸, 毕涛, 陈国凤, 郑东霞, 王周玉, 张园园. 基于D-半乳糖衍生的小分子半乳糖凝集素抑制剂的合成及活性研究进展[J]. 有机化学, 2022, 42(5): 1307-1325.
[6]	罗洁, 颜雅倩, 王浩鑫, 李瑶瑶. 新多环大环内酰胺Clifednamide K的发现[J]. 有机化学, 2022, 42(4): 1224-1228.
[7]	毛雅君, 邵香敏, 李阳杰, 曹瑞梅, 冯亚莉, 翟广玉. 槲皮素衍生物的合成研究进展[J]. 有机化学, 2022, 42(11): 3588-3605.
[8]	徐洪亮, 苏静, 王子时, 侯晨忻, 吴鹏冲, 邢月, 李香帅, 朱晓磊, 路运才, 徐利剑. 苯基吡咯类杀菌剂的设计合成及三维-定量构效关系(3D-QSAR)研究[J]. 有机化学, 2021, 41(9): 3560-3570.
[9]	章乐天, 苏嘉媛, 徐晓勇. 作为杀菌和杀虫先导的1,2,4-噁二嗪衍生物的设计与合成研究[J]. 有机化学, 2021, 41(9): 3539-3549.
[10]	周莎, 王目阔, 谢伟彬, 周沙, 熊丽霞, 赵毓, 李正名. 新型含N-COCF₃硫亚胺取代的手性双酰胺类化合物的合成与生物活性研究[J]. 有机化学, 2021, 41(9): 3532-3538.
[11]	邵继炎, 李志杰, 王迓君, 熊裕焱, 胡向东. 环庚三烯酮衍生物的合成和抑制胃癌细胞增殖的活性研究[J]. 有机化学, 2021, 41(9): 3675-3681.
[12]	朱海梦, 王超, 宗利利. 亚砜化合物的生物活性研究和不对称合成进展[J]. 有机化学, 2021, 41(9): 3431-3447.
[13]	江婷, 蒲洪, 段燕文, 颜晓晖, 黄勇. 深海、沙漠、火山、极地来源链霉菌新天然产物(2009~2020)[J]. 有机化学, 2021, 41(5): 1804-1820.
[14]	秦啸天, 张俊朝, 何钰晴, 张锐, 程华, 陈宬, 秦鑫. 含4-氨基二芳醚结构的辅酶Q衍生物的合成与生物活性研究[J]. 有机化学, 2021, 41(5): 2045-2054.
[15]	许萌, 高燊原, 曾源煦, 高安慧, 高立信, 许磊, 周宇波, 高建荣, 叶青, 李佳. 3-(吲哚-3-基)-4-(吡唑并[3,4-c]哒嗪-3-基)马来酰亚胺脱氢类异柠檬酸酶-1突变体高效抑制剂的合成与评价[J]. 有机化学, 2021, 41(5): 1991-2000.