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Pterostilbene amine compound containing isopropanol aromatic ether structure as well as preparation method and application of pterostilbene amine compound

A pterostilbene compound technology, applied in the field of pterostilbene compounds and their preparation, can solve the problems of endangering the safety of crops, increasing the resistance of plant pathogenic microorganisms, and affecting the environment

Pending Publication Date: 2021-04-09
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of traditional fungicides not only increases the resistance of plant pathogenic microorganisms but also affects the environment and endangers the safety of crops

Method used

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  • Pterostilbene amine compound containing isopropanol aromatic ether structure as well as preparation method and application of pterostilbene amine compound
  • Pterostilbene amine compound containing isopropanol aromatic ether structure as well as preparation method and application of pterostilbene amine compound
  • Pterostilbene amine compound containing isopropanol aromatic ether structure as well as preparation method and application of pterostilbene amine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the preparation of pterostilbene epoxy intermediate 1

[0054] Add 1.0 mmol of pterostilbene and 1.2 mmol of potassium carbonate into a 25 mL round bottom flask containing 10 mL of anhydrous DMF, and stir at room temperature until pterostilbene is completely dissolved. Continue to drop 1.3mmoL of epibromohydrin, and stir at 35°C for 8 hours until complete reaction. The reaction was stopped, and 50 mL of ethyl acetate was added, and the organic layer was washed with saturated ammonium chloride and saturated brine, dried over anhydrous sodium sulfate, precipitated, and subjected to column chromatography to obtain a white solid with a yield of 88.5%. Its NMR data are: 1 H NMR (400MHz, CDCl 3 )δ7.44 (d, J=8.7Hz, 2H, phenyl-H), 7.04 (d, J=16.3Hz, 1H, phenyl-C H =CH), 6.91 (dd, J=12.5, 3.7Hz, 3H, phenyl-CH=C H &phenyl-H), 6.66 (d, J=2.2Hz, 2H, phenyl-H), 6.39 (t, J=2.2Hz, 1H, phenyl-H), 4.23 (dd, J=11.0, 3.0Hz, 1H, 1 / 2phenyl-O-CH 2 ), 3.94 (dd, J=11.0, 5.7...

Embodiment 2

[0055] Example 2: (E)-1-amino-3-(4-(3,5-dimethoxystyryl)phenoxy)propan-2-ol

[0056] Add 1.0mmoL of pterostilbene epoxy intermediate 1 and 1.1mmoL of potassium carbonate into a round-bottomed flask containing 5mL of isopropanol, stir at room temperature until intermediate 1 is completely dissolved, then add 2.0mmoL of ammonia water dropwise, and heat to 60 After reacting at ℃ for 6 hours, the reaction was stopped, the solvent was removed by distillation under reduced pressure, and column chromatography gave a white solid with a yield of 85.1%.

[0057] Other target compounds were synthesized according to the steps of Examples 1 and 2 using corresponding raw materials or substituents. The structure, H-NMR and C-NMR data of the synthesized pterostilbene compounds containing isopropanol aromatic ether structure are shown in Table 1, and the physicochemical properties are shown in Table 2.

[0058] H NMR spectrum, C NMR data and high resolution mass spectrum data of the compounds...

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Abstract

The invention relates to a pterostilbene amine compound containing an isopropanol aromatic ether structure as well as a preparation method and application of the pterostilbene amine compound. The compound has a structure as shown in a general formula (I) which is described in the description. On the basis of a pterostilbene compound, fragments containing various aromatic amines and heterocyclic amines are introduced into the system to synthesize a series of isopropyl alcohol aromatic ether pterostilbene compounds containing various amine structures, and the compounds have a good inhibition effect on plant pathogenic microorganisms, and especially has a good inhibition effect on plant pathogenic bacteria such as xanthomonas oryzae pv. oryzae, xanthomonas axonopodis pv. citri, pseudomonas syringae pv. actinidiae, and plant pathogenic fungi such as botryosphaeria dothidea, rhizoctonia solani and anthracnose of pitaya.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a pterostilbene compound containing an isopropanol aromatic ether structure and a preparation method and application thereof. Background technique [0002] Bacterial and fungal diseases of plants, such as rice bacterial blight, pepper bacterial wilt, cabbage leaf spot, tobacco bacterial wilt, citrus canker, kiwifruit canker and cucumber gray mold, pepper fusarium wilt, rape fungus Sclerotinia, wheat head blight, potato late blight, blueberry root rot, grape sclerotium, pitaya anthracnose, rice sheath blight, etc. are several important diseases caused by plant pathogenic bacteria and fungi and affect crop production , mainly manifested as necrosis, withering, rot and other symptoms. The use of traditional fungicides not only increases the resistance of plant pathogenic microorganisms but also affects the environment and endangers the safety of crops. Therefore, there...

Claims

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Application Information

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IPC IPC(8): C07C217/32C07C217/58C07C217/90C07C213/04C07D211/22C07D213/36C07D295/088C07D307/52C07D333/20C07D303/23A01N43/36A01N43/40A01N43/60A01N43/08A01N43/10A01N33/10A01P1/00A01P3/00
CPCC07C217/32C07C217/90C07C217/58C07D295/088C07D211/22C07D213/36C07D307/52C07D333/20C07D303/23A01N43/36A01N43/40A01N43/60A01N43/08A01N43/10A01N33/10
Inventor 王培义王明伟周丽齐普应田欢雷立王优丹杨松薛伟
Owner GUIZHOU UNIV
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