Quinazolinone derivatives and production method and application thereof

A kind of technology of quinazolinone and derivatives, applied in the field of quinazolinone derivatives and preparation thereof, can solve problems such as no literature reports, and achieve the effects of low production cost, low toxicity and high yield

Active Publication Date: 2020-01-24
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] We have recently synthesized a new eight- or seven-membered heterocyc

Method used

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  • Quinazolinone derivatives and production method and application thereof
  • Quinazolinone derivatives and production method and application thereof
  • Quinazolinone derivatives and production method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of target product 1a

[0026]

[0027] (1) Under electromagnetic stirring, 4-chloroisatoic anhydride 2a (5mmol, 987mg) and methyl anthranilate (25mmol, 3780mg) were successively added to a 100mL round-bottomed flask, heated to reflux for 12h, and the crude product was Silica gel column chromatography purification (eluent: V 二氯甲烷 :V 石油醚 =1:1) to obtain 1124 mg of white solid compound 3a (yield 74%).

[0028] (2) Under electromagnetic stirring, compound 3a (5 mmol, 1520 mg), tetrahydrofuran (30 mL), lithium aluminum hydride (10 mmol, 380 mg) were sequentially added to a 1000 mL round bottom flask, and the mixture was heated at 0 °C After the reaction was complete, the reaction solution was adjusted to be alkaline with 10% NaOH solution until a white precipitate was formed, then suction filtered, and the filter cake was rinsed three times with dichloromethane, the filtrate was collected, and the solvent was removed under reduced pressure to obtain 840 mg of...

Embodiment 2

[0033] Synthesis of target product 1b

[0034]

[0035](1) Under electromagnetic stirring, 5-fluoroisatoic anhydride 2b (5mmol, 905mg) and methyl anthranilate (25mmol, 3780mg) were successively added to a 100mL round-bottomed flask, heated to reflux for 12h, and the crude product was Silica gel column chromatography purification (eluent: V 二氯甲烷 :V 石油醚 =1:1) to obtain 1036 mg of white solid compound 3b (yield 72%).

[0036] (2) Under electromagnetic stirring, compound 3b (5 mmol, 1440 mg), tetrahydrofuran (30 mL), lithium aluminum hydride (10 mmol, 380 mg) were sequentially added to a 100 mL round bottom flask, and the mixture was heated at 0 °C After the reaction was complete, the reaction solution was adjusted to be alkaline with 10% NaOH solution until a white precipitate was formed, then suction filtered, and the filter cake was rinsed three times with dichloromethane, the filtrate was collected, and the solvent was removed under reduced pressure to obtain 1112 mg of ...

Embodiment 3

[0041] Synthesis of target product 1c

[0042]

[0043] (1) Under electromagnetic stirring, 5-nitroisatoic anhydride (5mmol, 1040mg) and methyl anthranilate (25mmol, 3780mg) were successively added to a 100mL round-bottomed flask, heated to reflux for 12h, and the crude product was Silica gel column chromatography purification (eluent: V 二氯甲烷 :V 石油醚 =1:1), to obtain 2100 mg of white solid compound 3c (yield 67%).

[0044] (2) Under electromagnetic stirring, compound 3c (3.2 mmol, 1000 mg), tetrahydrofuran (30 mL), lithium aluminum hydride (6.4 mmol, 243 mg) were sequentially added to a 250 mL round bottom flask, and the mixture was heated at 0 °C After the reaction was complete, the reaction solution was adjusted to be alkaline with 10% NaOH solution until a white precipitate was formed, then suction filtered, and the filter cake was rinsed three times with dichloromethane, the filtrate was collected, and the solvent was removed under reduced pressure to obtain 470 mg of...

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Abstract

The invention discloses quinazolinone derivatives and a production method and application thereof. The quinazolinone derivatives are synthesized by means of the simple and convenient method, the yields are high, the production cost is low, with a concentration of 50 mM and an LPS concentration of 1 <mu>g/mL, the capability of compounds 1a, 1i, 1l and 1n of inhibiting release of NO is superior to that of an anti-inflammatory medicine indometacin, while the capability of 1b, 1e and 1j of inhibiting release of NO is equivalent to that of indometacin; and the cytotoxic effects of the compounds 1a,1i, 1l, 1n, 1b and 1j, with high capability of inhibiting release of NO, on RAW264.7 cells are all lower than that of the anti-inflammatory medicine indometacin. The quinazolinone derivatives have obvious anti-inflammatory effects and very low toxicity, can be made into anti-inflammatory medicines in various dosage forms, and have very high medical values and wide market prospects.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a quinazolinone derivative and a preparation method and application thereof. Background technique [0002] Quinazolinones are an important class of nitrogen-containing heterocyclic compounds, which appear in large quantities in various biologically active natural products and drug molecules, and their derivatives exhibit a wide range of biological activities, such as antitumor, antibacterial, antidiabetic, anti Viral, anti-inflammatory and anti-convulsant etc. Therefore, the synthesis method and biological activity of quinazolinone derivatives have always been a research hotspot in organic synthetic chemistry and medicinal chemistry, and hundreds of related documents are reported every year. [0003] We have recently synthesized a new eight- or seven-membered heterocyclic quinazolinone derivatives, which have not been reported in any literature so far. Contents of the invent...

Claims

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Application Information

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IPC IPC(8): C07D498/04C07D487/04A61P29/00
CPCA61P29/00C07D487/04C07D498/04
Inventor 潘成学孔翔飞郭秀云顾子钰莫冬亮苏桂发
Owner GUANGXI NORMAL UNIV
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