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
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,*()
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:
基金资助:
Jun He1, Xuemei Tang1, Qing Zhou1, Feng Peng1, Tingting Liu1, Liwei Liu1, Ming He1, Chengwei Xie1, Wei Xue1,*()
Received:
2020-08-07
Revised:
2020-09-04
Published:
2020-10-12
Contact:
Wei Xue
Supported by:
文章分享
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.
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.
Compd. | R | n | X. oryzae | X. citri | R. solanacearum | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
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 | X. citri | R. solanacearum | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
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 |
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 |
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