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Meridianin derivative as well as preparation and application thereof in prevention and treatment of plant virus and bacterial diseases

A technology for plant virus diseases and plant pathogens, which is applied in the fields of chemicals for biological control, botanical equipment and methods, applications, etc., which can solve the problem of increasing NFAT time, the biological activity of derivatives has not been systematically studied, and has not been systematically studied. research and reports on the issues, to achieve the effect of good anti-plant virus and fungus activity

Active Publication Date: 2020-02-07
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0035] In 2017, the Kinsella research group (Bioorg.Med.Chem.Lett.2017, 27, 2617-2621.) designed and synthesized a series of 6-azameridianins derivatives as DYRK inhibitors to increase NFAT (activated T cell nuclear factor ), and found that when the indole in the meridianin skeleton was changed to 6-azaindole, it could bind Dyrk1a (serine protein kinase) effectively and increase the time of NFAT in the nucleus, while the original meridianin skeleton molecule did not This effect (reaction eleven)
[0037] So far, although meridianin alkaloids have relatively mature synthetic routes and have been found to have certain anticancer activities, their other biological activities, especially the activities in the control of plant virus pathogens, have not been systematically studied and reported, in addition, the biological activities of their derivatives have not been systematically studied

Method used

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  • Meridianin derivative as well as preparation and application thereof in prevention and treatment of plant virus and bacterial diseases
  • Meridianin derivative as well as preparation and application thereof in prevention and treatment of plant virus and bacterial diseases
  • Meridianin derivative as well as preparation and application thereof in prevention and treatment of plant virus and bacterial diseases

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of Meridianin derivatives I-1 and I-2

[0052] I-1: In a 100mL round bottom flask, dissolve meridianin C (0.2g, 0.7mmol) in acetonitrile, and add Boc 2 O (0.18g, 0.84mmol), DMAP (0.07mmol, 0.01g), react at room temperature for two hours. After the reaction is complete, remove the solvent, add water, extract with dichloromethane, wash the organic phase with water, dry over anhydrous sodium sulfate, and concentrate under reduced pressure. Crude column chromatography (V 氯甲烷 :V 甲醇 =100:1→V 二氯甲烷 :V 甲醇 =20:1) to obtain 0.18 g of light yellow solid with a yield of 67% and a melting point of 171-173°C. 1 H NMR (400MHz, DMSO-d 6 )δ8.86(d, J=1.6Hz, 1H, Ar-H), 8.50(s, 1H, Ar-H), 8.25(d, J=5.2Hz, 1H, Ar-H), 8.07(d, J=9.2Hz, 1H, Ar-H), 7.56(dd, J=8.8, 1.6Hz, 1H, Ar-H), 7.21(d, J=5.2Hz, 1H, Ar-H), 6.77(s, 2H, NH 2 ), 1.67(s, 9H, C(CH 3 ) 3 ). 13 C NMR (100MHz, DMSO-d 6 )δ164.0, 160.7, 158.6, 148.9, 134.7, 129.8, 129.2, 128.1, 125.8, 118.1, 117...

Embodiment 2

[0054] Embodiment 2: the synthesis of Meridianin derivatives I-3

[0055] In a 100mL round bottom flask, the natural product meridianin C (0.5g, 1.7mmol) was dissolved in dry dichloromethane, DMAP (0.01g, 0.085mmol), p-toluenesulfonyl chloride (0.33g, 1.87 mmol), N, N-diisopropylethylamine (0.33g,, 2.55mmol), stirred at room temperature for 20h. After the reaction is complete, add 10% dilute hydrochloric acid to the system, extract with dichloromethane, wash once with water and once with saturated brine, dry over anhydrous sodium sulfate, and concentrate under reduced pressure. Crude column chromatography (V 二氯甲烷 :V 甲醇 =100:1→V 二氯甲烷 :V 甲醇 =20:1) to obtain 0.5 g of a light yellow solid with a yield of 62% and a melting point of 216-217°C. 1 H NMR (400MHz, DMSO-d 6 )δ8.83(d, J=2.0Hz, 1H, Ar-H), 8.73(s, 1H, Ar-H), 8.26(d, J=5.2Hz, 1H, Ar-H), 7.98(d, J=8.4Hz, 2H, Ar-H), 7.94(d, J=8.8Hz, 1H, Ar-H), 7.57(dd, J=8.8, 2.0Hz, 1H, Ar-H), 7.43(d, J=8.4Hz, 2H, Ar-H), 7.26(d, J=5.2H...

Embodiment 3

[0056] Embodiment 3: the synthesis of Meridianin derivatives I-4 and I-5

[0057] I-4: In a 100mL round bottom flask, dissolve meridianin D (0.5g, 1.7mmol) in acetonitrile, add potassium carbonate (0.5g, 3.4mmol), benzoyl chloride (0.24g, 1.7 mmol), stirred at room temperature for 12h. After the reaction is complete, remove the solvent, add water, extract with ethyl acetate, wash the organic phase with saturated brine, and dry over anhydrous sodium sulfate. Crude column chromatography (V 乙酸乙酯 :V 石油醚 =1:1) to obtain 0.39 g of a yellow solid with a yield of 57% and a melting point of 178-179°C. 1 H NMR (400MHz, DMSO-d 6 )δ8.74(d, J=8.4Hz, 1H, Ar-H), 8.53(s, 1H, Ar-H), 8.31-8.21(m, 2H, Ar-H), 7.91(d, J=7.6 Hz, 2H, Ar-H), 7.82(t, J=7.2Hz, 1H, Ar-H), 7.71(t, J=7.6Hz, 2H, Ar-H), 7.64(d, J=8.0 Hz, 1H, Ar-H), 7.18(d, J=5.2Hz, 1H, Ar-H), 6.78(s, 2H, NH2 ). 13 C NMR (100MHz, DMSO-d 6 ) δ168.9, 164.0, 160.4, 158.8, 137.6, 133.6, 133.2, 130.3, 130.0, 129.4, 127.5, 125.1, 119.3, 11...

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Abstract

The invention relates to a meridianin derivative I as well as a preparation method and application thereof in prevention and treatment of plant virus and bacterial diseases. The meridianin derivativeI disclosed by the invention shows especially excellent plant virus resisting activity, can well inhibit tobacco mosaic virus (TMV), and also shows certain plant pathogenic bacterium resisting activity.

Description

technical field [0001] The invention relates to meridianin derivatives and their preparation and application in the prevention and treatment of plant virus pathogens, belonging to the technical field of agricultural protection. Background technique [0002] The ocean is the largest treasure house of resources on the earth. Its unique marine environment (high salinity, high pressure, anoxic, low (constant) temperature, low (no) light) produces marine natural products with diverse biological activities and rich structures. So far, more than 25,000 natural products of marine biological origin have been found, and this number is still increasing by an average of 1,000 species per year (Nat.Prod.Rep.2014, 31, 160-258.; Nat.Prod .Rep.2017, 34, 235-294.). In the field of medicine, many marine natural products exhibit excellent medicinal activities such as antitumor, antibacterial, antiviral, and anticardiovascular diseases (Journal of Chengde Medical College 2017, 34, 332-336.); i...

Claims

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Application Information

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IPC IPC(8): C07D403/04C07D403/14C07D409/14A01N43/54A01P1/00A01P3/00
CPCC07D403/04C07D403/14C07D409/14A01N43/54Y02P20/55
Inventor 汪清民王兹稳董吉刘玉秀宋红健李永强
Owner NANKAI UNIV
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