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A kind of norcantharimid derivative and its preparation method and application

A technology of cantharimides and derivatives, which is applied in the field of norcantharimides derivatives and their preparation, can solve the problems of loss of normal diaphragm, cell death, vacuole increase, etc., and achieve the purpose of inhibiting plant pathogenic fungi, spreading The effect of spectral suppression

Inactive Publication Date: 2016-06-22
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Cantharidin has strong antibacterial activity against plant pathogenic fungi, which is mainly manifested in the increase of vacuoles in the mycelial protoplasts, the increase of cavities and the deposition of abnormal substances, resulting in the expansion and unevenness of mycelial cells, which in turn causes the expansion of mycelium Distorted growth, resulting in extravasation of intracellular material, loss of normal septum function, and ultimately cell death

Method used

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  • A kind of norcantharimid derivative and its preparation method and application
  • A kind of norcantharimid derivative and its preparation method and application
  • A kind of norcantharimid derivative and its preparation method and application

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preparation example Construction

[0042] The preparation method of above-mentioned norcantharidin amide derivatives adopts the following reactions to complete:

[0043]

[0044] where R is m-chlorophenyl or m-bromophenyl

[0045] Concrete preparation method is:

[0046] Add norcantharidin, m-chloroaniline (or m-bromoaniline), 1.5ml triethylamine, and 15ml toluene into a 100ml round-bottomed flask in sequence, and heat to reflux for 36 hours under constant stirring. After the reaction system was cooled at room temperature, a solid precipitated out. After filtration, it was recrystallized with a 2:5 (V:V) ethyl acetate-n-hexane mixed solvent to obtain white crystals, which were the target compound.

Embodiment 1

[0049] Compound N-(3'-chlorophenyl)norcantharimid and its synthesis (1a)

[0050]

[0051] In a round bottom flask, add 1.0g (5.95mmol) norcantharidin, 0.76g m-chloroaniline (1 equivalent), 1.5ml triethylamine, 15ml toluene in sequence, stir continuously, and heat to reflux for 36 hours. After the reaction system was cooled at room temperature, a solid precipitated out. After filtration, it was recrystallized with a 2:5 (V:V) ethyl acetate-n-hexane mixed solvent to obtain white crystals. product by 1 H-NMR spectrum and 13 C-NMR spectrum measurement, the analysis results are as follows figure 1 , figure 2 shown.

Embodiment 2

[0053] Compound N-(3'-bromophenyl)norcantharimid and its synthesis (1b)

[0054]

[0055] Add 1.0g (5.95mmol) norcantharidin, 1.02g m-bromoaniline (1 equivalent), 1.5ml triethylamine, and 15ml toluene to a 100ml round-bottomed flask in sequence, stir continuously, and heat to reflux for 36 hours. After the reaction system was cooled at room temperature, a solid precipitated out. After filtration, it was recrystallized with a 2:5 (V:V) ethyl acetate-n-hexane mixed solvent to obtain white crystals. product by 1 H-NMR spectrum and 13 C-NMR spectrum measurement, the analysis results are as follows image 3 , Figure 4 shown.

[0056] The physicochemical data of the prepared norcantharidin amide derivatives are shown in Table 1.

[0057] The physicochemical data of table 1 norcantharidin amides derivatives

[0058]

[0059] Examples of its bacteriostatic properties are given below.

[0060] (1) Weigh 100mg of the drug, dissolve it in 10mL of acetone, and prepare a 10mg / m...

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Abstract

The invention discloses a demethylcantharidin imide derivative and a preparation method and application thereof. 3'-chlorphenyl and 3'-bromophenyl are introduced into the structure of a demethylcantharidin derivative to form two demethylcantharidin imide derivatives: N-(3'-chlorphenyl)demethylcantharidin imide and N-(3'-bromophenyl)demethylcantharidin. The two compounds have broad-spectrum activity in suppressing plant pathogenic fungi, and can be used for preparing cantharidin agricultural drugs.

Description

technical field [0001] The invention belongs to the technical field of cantharidin derivatives, and relates to a norcantharimid derivative and its preparation method and application. Background technique [0002] Cantharidin, also known as cantharidin, is a terpene endogenous defense substance widely present in the cantharidin family insects such as cantharidin. Studies have found that it has tumor-inhibiting, insecticidal, and bactericidal activities, so it has high research value and has attracted widespread attention. However, cantharidin is highly toxic and complex to synthesize. Studies in recent years have shown that the compound norcantharidin (norcantharidin) after cantharidin lacks two methyl groups in the 2 and 3 positions not only maintains a strong anti-tumor activity, but also greatly reduces the toxicity, basically eliminating the effect of cantharidin on the human body. Toxic side effects of the urinary system. In addition, the synthesis steps and condition...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/18A01P3/00
CPCC07D491/18
Inventor 张雅林王阳孙文博郑胜礼
Owner NORTHWEST A & F UNIV