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Preparation method and application of natural product Streptochlorin and derivatives thereof

A technology of natural products and derivatives, applied in botany equipment and methods, chemicals for biological control, applications, etc., can solve the problem of less Streptochlorin and its derivatives

Inactive Publication Date: 2020-06-26
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] After reviewing relevant information, we learned that there are few patent reports on Streptochlorin and its derivatives, mainly focusing on the research on the inhibitory effect on cancer cells, and few related reports on its use as an agricultural fungicide

Method used

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  • Preparation method and application of natural product Streptochlorin and derivatives thereof
  • Preparation method and application of natural product Streptochlorin and derivatives thereof
  • Preparation method and application of natural product Streptochlorin and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Synthesis of Compound 5 (X=Cl, Streptochlorin)

[0065] 1. Synthesis of indole-3-carbaldehyde

[0066] Taking indole (compound 1) as raw material to synthesize raw material indole-3-carboxaldehyde (compound 2), the synthetic route is as follows:

[0067]

[0068] Take a 100mL round bottom flask, add 14.0mL of N,N-dimethylformamide, cool in an ice-water bath to 0-5°C; add POCl with a syringe 3 2.0mL, stirred in an ice-water bath for 30min; Dissolve 2.34g (20.0mmoL) of indole in 5mL of N,N-dimethylformamide, add and react at 35°C for 1h; cool, add H 2 O12.0mL, 26mL of 30% NaOH aqueous solution, heated to reflux for 30min; cooled, a large number of light yellow crystals naturally precipitated; filtered with suction, washed the solid with water several times to remove the alkali and N,N-dimethylformamide in the system; Weigh after drying. The calculated yield is 97%. Mp: 195.8-198.7°C. 1 H NMR (400MHz, DMSO) δ12.14(s, 1H), 9.94(s, 1H), 8.29(s, 1H), 8.10(d, J=7.2Hz, ...

Embodiment 2

[0082] After completing the framework construction of Streptochlorin according to the synthetic route of Example 1, carry out structural modification to it, the modification site is concentrated on the free NH position of the indole ring, and combine it with different halogenated groups RX in the base of sodium hydride Under neutral conditions, the reaction ranges from 0.25 to 3 hours in the temperature range from room temperature to 100 °C. The obtained compounds were 1 H NMR, 13 Confirmation by C NMR, IR and HRMS.

[0083] 1. Synthesis of compound I-3

[0084] Compound 5 (X=Cl) (0.20mmoL) was obtained by using the synthesis route of Example 1 above. Take 3mL of anhydrous tetrahydrofuran and stir to dissolve; under ice-water bath conditions, add sodium hydride (60%, 0.30mmoL) and react at room temperature for 30min ; Add 2mL of anhydrous tetrahydrofuran containing allyl bromide (0.24mmoL), react at room temperature for 2h, and monitor the progress of the reaction by TLC. ...

Embodiment 3

[0174] The heating conditions in the reaction conditions have been further optimized. Some compounds are heated by microwaves. After screening the reaction temperature, solvent, radiation intensity and other conditions, the microwave reaction only takes 15 minutes to obtain the target compound. The obtained compounds were 1 H NMR, 13 Confirmation by C NMR, IR and HRMS.

[0175] 1. Synthesis of compound I-18:

[0176] After the compound 5 (X=Cl) was obtained by using the synthesis route of the above-mentioned Example 1, the method of microwave-assisted organic synthesis was adopted, and microwave reaction tubes were taken to add microwave magnets, compound 4 (X=Cl) (0.20mmol) and anhydrous Tetrahydrofuran 5mL (dried and re-distilled), after stirring and dissolving, add sodium hydride (60%, 0.40mmol), add a drying tube to react for 20min, add bromomethylcyclopropane (0.24mmol), seal the tube and put it in microwave reaction React in the container for 15 minutes, and the react...

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Abstract

The invention discloses a preparation method of a derivative of a natural product Streptochlorin. The invention also discloses an application of the natural product Streptochlorin and the derivative thereof in killing pathogenic bacteria of crops. The natural product Streptochlorin and the derivative thereof have the advantages that the bactericidal activity is good, can be applied to crop diseases caused by fungi, bacteria and viruses, and show efficient and / or broad-spectrum bactericidal activity.

Description

technical field [0001] The invention relates to an agricultural fungicide, in particular to a preparation method of the natural product Streptochlorin and its derivatives and their application in sterilization. Background technique [0002] The natural product Streptochlorin is a small molecule indole alkaloid isolated from marine Streptomyces sp. by Japanese scientist H.Watanabe et al. in 1988. Its structure was identified as 4-chloro-5-( 3'-indolyl)-oxazole. According to literature reports, Streptochlorin has anti-angiogenic, anti-microbial, anti-cell proliferation and anti-cancer activities. The compound can also effectively inhibit endothelial cell invasion and microtubule formation stimulated by vascular endothelial growth factor (VEGF) at micromolar concentrations. It is not toxic to normal cells. In addition, Streptochlorin was able to inhibit TNF-α-induced NF-κB activation in a newly developed cell-based reporter assay. [0003] According to relevant information, ...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D413/14A01N43/76A01P1/00A01P3/00
CPCC07D413/04C07D413/14A01N43/76
Inventor 张明智施展刘畅章维华
Owner NANJING AGRICULTURAL UNIVERSITY
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