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Cyanoacrylate derivatives and their preparation method and biological activity

A technology of cyanoacrylic acid and its derivatives, which can be used in botany equipment and methods, organic active ingredients, biocides, etc., and can solve problems such as activity decline

Inactive Publication Date: 2005-04-06
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The herbicidal activity of the synthesized compound was determined by pot planting method. The bioassay results showed that the cyanoacrylate compound after replacing benzene with pyridine had better herbicidal activity. The high herbicidal activity is still maintained after radical replacement, but with the increase of the alkoxy group, the activity tends to decrease slightly

Method used

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  • Cyanoacrylate derivatives and their preparation method and biological activity
  • Cyanoacrylate derivatives and their preparation method and biological activity
  • Cyanoacrylate derivatives and their preparation method and biological activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1, the synthesis of 3-p-trifluoromethylaniline-3-methylthio-2-cyanoacrylate (the compound number is a):

[0049] (1) Synthesis of 3,3-dimethylthio-2-cyanoacrylate:

[0050] After adding 400mL of absolute ethanol, 34.0g (0.301mol) of ethyl cyanoacetate, and 23.0g (0.303mol) of carbon disulfide into a 1000mL four-necked bottle, the temperature was controlled to be less than 20°C, and 360mL of sodium ethoxide (0.610M) with a concentration of 1.7M was added dropwise. mol), the dropwise addition time is about 1h, after the dropwise addition is completed, stir at room temperature for 8h, then add dropwise 38.5g dimethyl sulfate (0.305mol), dropwisely complete in 30min, heat to reflux for 2.5h, and the reaction is complete. The reaction system was poured into 500mL of water and allowed to stand overnight to obtain a white needle-like solid, which was suction filtered and dried. Recrystallized twice with n-hexane: ether (1:1) to obtain 36.7 g of white crystals, name...

Embodiment 2

[0054]Example 2, Synthesis of 3-(2,6-dichloro-4-trifluoromethyl)aniline-3-methylthio-2-cyanoacrylate (compound number is b):

[0055] (1) Synthesis of 3,3-dimethylthio-2-cyanoacrylate,

[0056] Synthesize as in Example 1 (1) method and conditions.

[0057] (2) Synthesis of 3-(2,6-dichloro-4-trifluoromethyl)aniline-3-methylthio-2-cyanoacrylate:

[0058] 2.17g (0.01mol) of 3,3-dimethylthio-2-cyanoacrylate, 2.30g (0.01mol) of 2,6-dichloro-4-trifluoromethylaniline were added to a 50mL three-necked flask, and 0.80 60% NaH (0.02mol) was added, then 20mL of DMF and 20mL of toluene mixed solvent was added dropwise, the temperature of the addition was controlled below 10°C, and after stirring at room temperature for 40h, the reaction was complete. Pour the reaction system into 100 mL of ice water, separate the water phase, slowly adjust the pH with 10% HCl, a light yellow solid precipitates, dry it, and recrystallize it with ethanol to obtain 2.61 g of white crystals, namely 3-(2,6-d...

Embodiment 3

[0060] Example 3, Synthesis of 3-(4-methylbenzothiazole-2-)amine-3-methylthio-2-cyanoacrylate (compound number is d):

[0061] (1) Synthesis of 3,3-dimethylthio-2-cyanoacrylate,

[0062] Synthesize as in Example 1 (1) method and conditions.

[0063] (2) Synthesis of 3-(4-methylbenzothiazole-2-)amine-3-methylthio-2-cyanoacrylate: 3,3-dimethylthio-2-cyanoacrylate 2.65 g (0.012mol), and 2.0g (0.012mol) of 2-amino-4-methylbenzothiazole were added to a 100mL three-necked flask. After adding 0.96g (0.024mol) of 60% NaH, then dropwise add 25mL of toluene and 25mL of DMF as a mixed solvent, use an ice bath to control the dropwise addition temperature not to exceed 20°C, and complete the dropwise addition in about 10min, after stirring at room temperature for 48h, TLC traced the completion of the reaction . The reaction system was poured into 150 mL of ice water, the water phase was separated, and 10% HCl solution was added dropwise, and milky yellow solids were precipitated. When t...

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Abstract

This invention discloses a medicine of anti-tumor and anti-plant virus effect---- cyanoacrylate category derivative and its preparing method and biological activity. The following general formula denotes the compound and its preparing method. The definition of R1, R2, R3 in the formula is in instruction book. Materials are carbon bisulfide, cyan acetic ester, dimethyl sulfate, aromatic amine, and sodium cyanide is catalyst, cyanoacrylate category derivative is synthesized by three steps. There is proliferation inhibitory effect of compound b, k to PC3 prostate cancer cell gene stock, and proliferation inhibitory effect of compound i, j to NIN3T3 cell ERK albumen phosphorylation, and good anti-cancer activity is revealed. There is inhibitory activity of compound b, n to tobacco mosaic, and certain anti-plant virus activity is revealed.

Description

technical field [0001] The medicine with anti-tumor and anti-plant virus effects of the invention is a cyanoacrylate derivative and a preparation method thereof. [0002] Selecting photosynthesis as the target of herbicides is the need of creating green pesticides in the world today. In 1985, Deisenhofer (Deisenkorfer.J, Epp.O.Miki.K.et al, Nature, 1985, 318 (12): 618) adopted X -Diffraction method successfully solved the three-dimensional structure of the electron transfer system protein in the photosynthesis of Violet fungus. This research result makes the new photosynthesis inhibitor designed based on the receptor model a research hotspot in the world today. The research shows that 2-cyanoacrylic acid Ester is a class of important herbicides that inhibit plant photosynthesis. It acts on the same target—the plastoquinone QB binding site in PSII of photosynthesis, and competitively replaces the plastoquinone QB bound to the D1 protein, resulting in the blockage of electron tr...

Claims

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Application Information

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IPC IPC(8): A01N47/40A61K31/275A61K31/428A61K31/44A61P35/00C07C255/30C07C323/58C07D213/72C07D277/82
Inventor 杨松金林红宋宝安钟惠民刘刚
Owner GUIZHOU UNIV
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