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2-substituted pyridyl quinazolinone derivative and synthesis method and application thereof

A technology of pyridyl quinazolinone and dimethyl quinazoline, which is applied in the field of chemistry, can solve the problems of anti-bacteria that have not been reported, and achieve good activity effect

Active Publication Date: 2017-04-26
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are no reports about the compounds that the pyridine heterocycle is directly connected to the quinazolinone structure and the antibacterial aspects of such compounds

Method used

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  • 2-substituted pyridyl quinazolinone derivative and synthesis method and application thereof
  • 2-substituted pyridyl quinazolinone derivative and synthesis method and application thereof
  • 2-substituted pyridyl quinazolinone derivative and synthesis method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Embodiment 1, the synthetic method of 6-chloro-2-(2-chloropyridin-3-yl)-3,8-dimethylquinazolin-4(3H)-one (a), comprises the following steps:

[0034] (1) Synthesis of 2-chloronicotinyl chloride:

[0035] In a 100mL round bottom flask, add 2-chloronicotinic acid (2.00g, 12.69mmol), thionyl chloride (1.84mL, 25.38mmol), N,N-dimethylformamide (0.37g, 5.08mmol) and stir , heated to reflux for 8 hours, evaporated under reduced pressure to remove excess thionyl chloride, and obtained a yellow solid, namely 2-chloronicotinoyl chloride, which was directly used in the next reaction without purification.

[0036] (2) Synthesis of 2-chloro-N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)nicotinamide:

[0037]In a 100mL three-necked flask, add 2-amino-5-chloro-3-methylbenzamide (8.06g, 40.58mmol), 30mL dichloromethane, N,N-diisopropylamine ethylamine (8.39g, 64.93mmol ), stirred at room temperature for 30 minutes, slowly added dropwise the newly prepared dichloromethane solution o...

Embodiment 2

[0041] The synthetic method of embodiment 2, 6-chloro-2-(2-(cyclopropylamino)pyridin-3-yl)-3,8-dimethylquinazolin-4(3H)-one (b) , including the following steps:

[0042] (1) step is with embodiment 1 (1) step;

[0043] (2) step is with embodiment 1 (2) step;

[0044] (3) step is with embodiment 1 (3) step;

[0045] (4) In a 50mL three-necked flask, add 6-chloro-2-(2-chloropyridin-3-yl)-3,8-dimethylquinazolin-4(3H)-one (1.00g, 3.12mmol ), KI (0.15g, 0.92mmol), dimethyl sulfoxide 10mL, stirred at room temperature for 10min, added cyclopropylamine (0.36g, 6.25mmol), after addition, reacted at room temperature for 30min, heated to 100°C, followed by TLC for 48h After the reaction was complete, the reflux device was removed, 20 mL of ice water was added, the solid was suction filtered, and the filter cake was washed three times (10×3) mL with ice water to obtain a crude product, which was then recrystallized with absolute ethanol and naturally dried in a fume hood to obtain whit...

Embodiment 3

[0047] Example 3, 6-chloro-3,8-dimethyl-2-(2-(4-methylpiperazin-1-yl)pyridin-3-yl)quinazolin-4(3H)-one ( c) the synthetic method, comprises the following steps:

[0048] (1) step is with embodiment 1 (1) step;

[0049] (2) step is with embodiment 1 (2) step;

[0050] (3) step is with embodiment 1 (3) step;

[0051] (4) In a 50mL three-necked flask, add 6-chloro-2-(2-chloropyridin-3-yl)-3,8-dimethylquinazolin-4(3H)-one (1.00g, 3.12mmol ), KI (0.15g, 0.92mmol), dimethyl sulfoxide 10mL, stirred at room temperature for 10min, added N-methylpiperazine (0.62g, 6.25mmol), added, reacted at room temperature for 30min, heated to 100°C, TLC Follow up the reaction, after 48 hours the reaction is complete, remove the reflux device, add 20mL of ice water, filter the solid with suction, wash the filter cake with ice water three times (10×3) mL to obtain a crude product, then recrystallize with absolute ethanol and dry naturally in a fume hood White crystals were obtained.

[0052] H NM...

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Abstract

The invention discloses a 2-substituted pyridyl quinazolinone derivative and a synthesis method and application thereof. A general structural formula of the derivative is show as the following (I), wherein R represents one of Cl, CH3CH2NH, CH3CH2CH2NH, (CH3)2CHNH, CH3CH2CH2CH2NH, NH2CH2CH2NH and PhCH2NH. The 2-substituted pyridyl quinazolinone derivative has the advantages of having the activity of resisting rice xanthomonas oryzae, tobacco pseudomonas solanacearum and xanthomonas Campestris pv.citri. The formula (I) is defined in the description.

Description

technical field [0001] The present invention relates to the field of chemical technology, specifically to a kind of 2-substituted pyridyl quinazolinone derivatives, also relates to the preparation method of the 2-substituted pyridyl quinazolinone derivatives, and the 2-substituted pyridyl quinazolinone derivatives Use of substituted pyridyl quinazolinone derivatives in inhibiting rice bacterial blight, tobacco bacterial wilt and citrus canker. Background technique [0002] Pyridine is the biological isostere of benzene ring, which has similar structure and properties with benzene ring. When replacing benzene ring with pyridine ring, because the pyridine ring has better systemic property, it can often significantly improve the biological activity and at the same time Significantly reduces toxicity. Quinazolinone derivatives have a wide range of biological activities, such as: antibacterial, anticancer, insecticidal and other biological activities. Therefore, a pyridine hete...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/54A01P3/00A01P1/00A01P7/04A01P13/00
CPCA01N43/54C07D401/04
Inventor 欧阳贵平陈琴涂红邰安琪
Owner GUIZHOU UNIV
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