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Glyantryine family alkaloid derivative, preparation thereof and application of Glyantryine family alkaloid derivative in prevention and treatment of plant viruses, pathogenic bacteria and diseases

A technology of alkaloid derivatives and plant pathogens, applied in the field of agricultural protection

Pending Publication Date: 2022-07-29
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no report about the synthesis method of Glyantrypine family alkaloid derivatives I-1~I-10 and the use of Glyantrypine family alkaloid derivatives in the prevention and treatment of plant virus pathogens

Method used

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  • Glyantryine family alkaloid derivative, preparation thereof and application of Glyantryine family alkaloid derivative in prevention and treatment of plant viruses, pathogenic bacteria and diseases
  • Glyantryine family alkaloid derivative, preparation thereof and application of Glyantryine family alkaloid derivative in prevention and treatment of plant viruses, pathogenic bacteria and diseases
  • Glyantryine family alkaloid derivative, preparation thereof and application of Glyantryine family alkaloid derivative in prevention and treatment of plant viruses, pathogenic bacteria and diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: Synthesis of Glyantrypine family alkaloid derivative I-1.

[0016] The first step, the synthesis of intermediate 3. Isatoic anhydride (1) (15 g, 92 mmol) and L-tryptophan methyl ester hydrochloride (2) (24 g, 92 mmol), triethylamine (14 mL, 96.6 mmol) were added to acetonitrile and heated at 80°C. TLC detected the end of the reaction, spin off most of the solvent, add ethyl acetate to dissolve, wash the organic phase with saturated brine, and recrystallize with petroleum ether / ethyl acetate to obtain 26 g of yellow solid, yield 85%, melting point 125-127°C . 1 H NMR (400MHz, CDCl 3 )δ8.21(s, 1H), 7.56(d, J=7.9Hz, 1H), 7.34(d, J=8.1Hz, 1H), 7.20-7.15(m, 3H), 7.10(t, J=7.5 Hz, 1H), 6.99 (d, J=1.9Hz, 1H), 6.69-6.59 (m, 2H), 6.55 (t, J=7.5Hz, 1H), 5.48 (s, 2H), 5.08 (dd, J =12.8, 5.4Hz, 1H), 3.71(s, 3H), 3.42(dd, J=5.2, 1.9Hz, 2H). 13 C NMR (100MHz, CDCl 3 ) δ172.6, 168.8, 148.9, 136.2, 132.6, 127.6, 127.6, 122.9, 122.3, 119.7, 118.7, 117.3, 116.6, 115.3, 1...

Embodiment 2

[0019] Example 2: Synthesis of Glyantrypine family alkaloid derivative I-2.

[0020] The first step, the synthesis of intermediate 4b. Intermediate 3 (5 g, 14.8 mmol) and Fmoc-L-ala-Cl (5.6 g, 17.8 mmol) were added to dichloromethane, and the reaction was carried out at room temperature overnight. The reaction was detected by TLC, and quenched by adding saturated sodium carbonate solution. The organic phase was washed with brine, and recrystallized from dichloromethane / petroleum ether to obtain 6.7 g of a yellow solid with a yield of 83% and a melting point of 128-130°C. 1 H NMR (400MHz, CDCl 3 )δ11.49(s, 1H), 8.58(d, J=8.2Hz, 1H), 8.15(s, 1H), 7.76(d, J=7.2Hz, 2H), 7.66(d, J=6.4Hz, 1H), 7.61-7.55(m, 1H), 7.52-7.44(m, 2H), 7.43-7.37(m, 2H), 7.37-7.27(m, 4H), 7.17(t, J=7.5Hz, 1H) , 7.09-7.03(m, 1H), 6.99(t, J=7.6Hz, 1H), 6.95(s, 1H), 6.73(d, J=7.4Hz, 1H), 5.55(d, J=6.2Hz, 1H), 5.04(dd, J=12.5, 5.2Hz, 1H), 4.50-4.32(m, 3H), 4.30-4.23(m, 1H), 3.73(s, 3H), 3.44-3.31(m, 2H) , ...

Embodiment 3

[0022] Example 3: Synthesis of Glyantrypine family alkaloid derivative I-3.

[0023] The first step, the synthesis of intermediate 8. Anthranilic hydrazide (6) (1.51g, 10mmol) and phthalic anhydride (7) (1.48g, 10mmol) were added to ethylene glycol, heated at 150°C, TLC detected the disappearance of the raw materials, cooled to room temperature, and pumped under reduced pressure. After filtering, the filter cake was washed with ethyl acetate to obtain 2.1 g of a khaki solid with a yield of 80% and a melting point of 288-290°C. 1 H NMR (400MHz, DMSO-d 6 )δ8.82(d, J=7.5Hz, 1H), 8.28(dd, J=8.0, 1.0Hz, 1H), 8.20(d, J=7.6Hz, 1H), 8.05-7.93(m, 2H), 7.93-7.89(m, 1H), 7.88-7.84(m, 1H). 7.64-7.56(m, 1H).

[0024] The second step, the synthesis of intermediate 9. Intermediate 8 (1 g, 3.8 mmol) was added to POCl 3 , heated at 90°C, TLC detected the disappearance of the raw materials, cooled to room temperature, slowly poured the reaction solution into ice water, and filtered under r...

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Abstract

The invention relates to alkaloid derivatives I-1-I-10 of a Glyantryine family, a preparation method of the alkaloid derivatives I-1-I-10 and application of the alkaloid derivatives I-1-I-10 in prevention and treatment of plant viruses, pathogenic bacteria and diseases. The alkaloid derivatives I-1 to I-10 of the Glyantryine family show anti-plant virus activity, can well inhibit tobacco mosaic virus, and meanwhile, the compounds also show broad-spectrum anti-plant germ activity, and have outstanding inhibitory activity on apple ring spot bacteria.

Description

technical field [0001] The invention relates to a Glyantrypine family alkaloid derivative and its preparation and application in preventing and controlling plant virus disease, belonging to the technical field of agricultural protection. Background technique [0002] The Glyantrypine family of alkaloids is a large class of alkaloids containing a pyrazine[2,1-b]quinazoline-3,6-dione skeleton and linked to indole, mainly from the secondary metabolites of marine and terrestrial fungi. In 1992, Mantle's research group at Imperial College London isolated glyantrypine alkaloids from the secondary metabolites of Aspergillus clavatus, and identified their structures by biosynthesis analysis, mass spectrometry, and hydrogen nuclear magnetic resonance spectroscopy (J.Chem.Soc. , Perkin Trans 11992, 1495-1496.). In 1995, the Numata group at Osaka Pharmaceutical University isolated seven new fumiquinazolines (FQs) A-G alkaloids from the deep-sea fish Pseudolabrus japonicus gastrointest...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D471/04A01N43/90A01P1/00A01P3/00
CPCC07D487/04C07D471/04A01N43/90
Inventor 汪清民王兹稳郝亚男刘玉秀
Owner NANKAI UNIV
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