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Camelinine A derivative as well as preparation and application thereof in prevention and treatment of plant virus and pathogenic bacterial diseases

A technology of camelamine and plant pathogens, applied in the field of agricultural protection, can solve the problems that cytotoxicity is not directly related

Pending Publication Date: 2022-02-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] In 2007, Jason Herr (Bioorg.Med.Chem.2007, 15, 4237-4246.) of the Albany Molecular Research Company in the United States found that 3-fluorocameline A has a strong inhibitory activity on Topo I, which is similar to the inhibitory activity of CPT Comparable, but not directly related to the cytotoxicity of CPT
On the other hand, in 2004, the Chavan research group of the State Key Laboratory of Organic Chemistry in India (Tetrahedron Lett.2004, 60, 9931-9935.) found that 14-ethyl cameline A was more cytotoxic than cameline A. slightly improved

Method used

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

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the synthesis of cameline A derivative I-1~I-12

[0015] The first step, the synthesis of intermediate 3. Dissolve anthranilamide (1) (5g, 37mmol) in chloroform, add triethylamine (14mL), slowly add o-nitrobenzoyl chloride (2) (7mL, 52mmol) under stirring, and react at room temperature for four hours , TLC detects that the reaction is complete, and suction filtration under reduced pressure gives 4.2 g of a white solid, with a yield of 80%, and a melting point of 195-197 ° C. 1 H NMR (400MHz, DMSO-d 6 )δ12.52(s, 1H), 8.48(d, J=8.2Hz, 1H), 8.38(brs, 1H), 8.11(d, J=8.1Hz, 1H), 7.92-7.75(m, 5H), 7.59(t, J=7.7Hz, 1H), 7.23(t, J=7.6Hz, 1H).

[0016] The second step is the synthesis of intermediate 4. Intermediate 3 (4g, 14mmol) was dissolved in 10% KOH aqueous solution (40mL) and absolute ethanol (20mL), heated to reflux at 90°C, TLC detected that the reaction was complete, most of the solvent was spin-dried, and extracted with ethyl acetate , dried over an...

Embodiment 2

[0030] Embodiment 2: the synthesis of cameline A derivative I-12

[0031] Compound 8 (600mg, 2mmol) was dissolved in THF, protected by oxygen, heated at 100°C by TLC to detect the completion of the reaction, diluted with water, extracted with methyl tert-butyl ether, dried with anhydrous sodium sulfate, filtered with suction, precipitated under reduced pressure, column Chromatography (V (petroleum ether): V (ethyl acetate) = 10: 1) gave 480 mg of a light yellow solid with a yield of 61% and a melting point of 131-133°C. 1 H NMR (400MHz, CDCl 3 )δ8.82(d, J=7.9Hz, 1H), 8.23(d, J=8.0Hz, 1H), 7.87-7.76(m, 4H), 7.65(t, J=6.8Hz, 1H), 7.59( d, J=7.9Hz, 1H), 7.50-7.38(m, 3H). 13 C NMR (100MHz, CDCl 3 )δ159.8, 146.9, 146.6, 145.3, 142.0, 136.1, 135.7, 135.4, 133.7, 131.9, 129.8, 129.3, 129.0, 128.1, 127.6, 127.5, 127.3, 126.7, 126.2, 121.7, 119 for C 21 h 12 Cl 2 N 3 O[M+H] + 392.0352, found 392.0353.

Embodiment 3

[0032] Embodiment 3: the assay of anti-tobacco mosaic virus activity, assay procedure is as follows:

[0033] 1. Virus purification and concentration determination:

[0034] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the crude virus extract was centrifuged twice with polyethylene glycol, the concentration was measured and refrigerated at 4°C for later use.

[0035] 2. Compound solution preparation:

[0036] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL mother solution, and then diluted with 1‰ Tween 80 aqueous solution to the required concentration; Ningnanmycin preparation was directly diluted with water.

[0037] 3. In vivo protection:

[0038] Select Shanxi tobacco with uniform growth at the 3-5 leaf stage, spray the whole plant, and repeat each treatment 3 t...

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PUM

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Abstract

The invention relates to camelinine A derivatives I-1 to I-12, a preparation method thereof and application of the camelinine A derivatives in prevention and treatment of plant virus and pathogenic bacterial diseases. The tryptanthrin derivatives I-1 to I-12 disclosed by the invention show anti-plant virus activity, can well inhibit tobacco mosaic virus; meanwhile, the compounds also show broad-spectrum anti-plant germ activity, and have outstanding inhibitory activity on physalospora piricola.

Description

technical field [0001] The invention relates to a cameline A derivative and its preparation and application in the prevention and treatment of plant virus and bacterial diseases, and belongs to the technical field of agricultural protection. Background technique [0002] In 2007, Jason Herr (Bioorg.Med.Chem.2007, 15, 4237-4246.) of the Albany Molecular Research Company in the United States found that 3-fluorocameline A has a strong inhibitory activity on Topo I, which is similar to the inhibitory activity of CPT Comparable, but not directly related to the cytotoxicity of CPT. 3-N, N-diethylaminoethoxy and 3-N, N-dimethylaminoethoxy cameline A have the effect of improving the toxicity of HCT-116 tumor cells (human colon cancer cell line). It is worth noting that in 2004, the Dallavalle research group of the University of Milan (Bioorg.Med.Chem.Lett.2004, 14, 5757-5761.) found that 2,3-dimethoxy camelline A was mediated by topo-I The DNA cleavage of H460 (human non-small lun...

Claims

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Application Information

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IPC IPC(8): C07D487/04A01N43/90A01P3/00A01P1/00
CPCC07D487/04A01N43/90
Inventor 汪清民郝亚男刘玉秀王兹稳宋红健李永强
Owner NANKAI UNIV
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