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1, 4-disubstituted 3, 4-dihydro-2 (3H)-quinazolinone compound as well as synthesis method and application thereof

A technology of quinazolinones and compounds, applied in the field of organic synthesis and medicine, capable of solving problems that have not yet been reported

Active Publication Date: 2020-11-27
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, 3,4-dihydro-2(3H)-quinazolinones have not been reported

Method used

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  • 1, 4-disubstituted 3, 4-dihydro-2 (3H)-quinazolinone compound as well as synthesis method and application thereof
  • 1, 4-disubstituted 3, 4-dihydro-2 (3H)-quinazolinone compound as well as synthesis method and application thereof
  • 1, 4-disubstituted 3, 4-dihydro-2 (3H)-quinazolinone compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Example 1 Compound 2a

[0088]

[0089] Under nitrogen protection, magnesium (0.4g, 17.8mmol) was added to tetrahydrofuran THF (20mL), then a grain of iodine (diameter 0.2mm, about 10mg) was added, and heated to 70°C. Then 2-methylbromobenzene (3 g, 17.5 mmol) was added and reacted at 70° C. for 1 hour. Afterwards, the solution was transferred to a THF solution (20 mL) of 2-nitrobenzaldehyde (2.65 g, 17.5 mmol) and reacted at room temperature for 1 hour. After the reaction solution was quenched with water, it was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Solvent was removed using a rotary evaporator. The obtained crude product was purified by silica gel column chromatography. The product 3.6g (14.8mmol) was obtained, the yield was 85%, white solid.

Embodiment 2

[0090] Example 2 compound 3a example

[0091] Compound 3a

[0092]

[0093] Chromium trioxide pyridine hydrochloride (PCC) (90mmol) in dichloromethane (20mL) was added dropwise to compound 2a (3.6g, 14.8mmol) in dichloromethane (50mL) at room temperature, stirred at room temperature for 5h , the reaction solution was filtered through celite, washed with ether, and the solvent was removed by a rotary evaporator. The obtained crude product was purified by silica gel column chromatography to obtain 3.2 g (13.2 mmol) of the product, with a yield of 90%, as a pale yellow solid.

Embodiment 3

[0094] Example 3 Compound 4 Example

[0095] Compound 4a

[0096]

[0097] Compound 3a (3g, 12.4mmol), ethanol (15mL), water (15mL) and iron powder (14g, 249mmol) were mixed and heated at 40°C for 30 minutes, then hydrochloric acid (2mL, 12mol / L) was added, and React for 2 hours. The solution was filtered through celite and washed with saturated sodium bicarbonate. After extraction with dichloromethane, the organic layer was dried over anhydrous sodium sulfate. Solvent was removed by rotary evaporator. The obtained crude product was purified by silica gel column chromatography. The product was obtained in 2.5 g (12 mmol), 95% yield, as a pale yellow solid.

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Abstract

The invention belongs to the field of organic synthesis and medicines, and particularly relates to a 1, 4-disubstituted 3, 4-dihydro-2 (3H)-quinazolinone compound as well as a synthesis method and application thereof. R1 is hydrogen or chlorine, R2 is hydrogen, methyl, methoxyl or fluorine, R3 is nitrophenyl, (2-trifluoromethyl-5-Cl) piperidyl, phenyl, methoxyl phenyl, methyl phenyl, 2-trifluoromethyl phenyl or C2-C8 alkyl or naphthenic base, R4 is hydrogen or methyl, and X is O or S. The compound is a novel compound with a non-peptide structure, has a good inhibitory effect on cancer cells, has a broad-spectrum effect, especially has good inhibitory activity on hepatoma carcinoma cells, and has good market prospects and application prospects.

Description

technical field [0001] The invention belongs to the field of organic synthesis and medicine, and specifically relates to a 1,4-disubstituted 3,4-dihydro-2(3H)-quinazolinone compound and a synthesis method and application thereof. Background technique [0002] Quinazolinones and their derivatives are widely used in the medical field due to their structural variability and broad-spectrum biological activities. CN 106632092 A shows that 4-quinazoline derivatives and 2,4-quinazoline derivatives can be used for DHQA medicine and antibacterial. In DE2702530A1, Sumitomo Chemical Co., Ltd. first mentioned an important 4-dihydro-2(1H)-quinazolinone derivative in 1976. The prior art shows that derivatives with different substituents at the 3 and 4 positions are good Na + / Ca 2+ Ion exchange inhibitor, which can be used for related treatment of ischemic heart disease; CN 101255138A discloses derivatives with 3, 4-substituted 2(1H)-quinazoline structures, which have anticoccidial act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/82C07D239/78C07D401/04A61P35/00A61P35/02
CPCC07D239/82C07D239/78C07D401/04A61P35/00A61P35/02C07B2200/07
Inventor 孙智华王圆圆戴伊如
Owner SHANGHAI UNIV OF ENG SCI