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Chalcone analogue containing 2-methyl-4-oxo-quinazoline-6-base, and preparation method and application thereof

A technology of methylquinazoline and oxoquinazoline, which is applied in the application field of chalcone analogues and antitumor drugs, and can solve problems that do not involve 2-methyl-4-oxoquinazoline Chalcone analogues and other issues

Inactive Publication Date: 2015-07-29
CAPITAL NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Nevertheless, no chalcone analogs comprising 2-methyl-4-oxoquinazolines are known in the prior art

Method used

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  • Chalcone analogue containing 2-methyl-4-oxo-quinazoline-6-base, and preparation method and application thereof
  • Chalcone analogue containing 2-methyl-4-oxo-quinazoline-6-base, and preparation method and application thereof
  • Chalcone analogue containing 2-methyl-4-oxo-quinazoline-6-base, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] (E)-6-(3-Phenylacryloyl)-2-methylquinazolin-4(3H)-one (Compound 1)

[0125] Yield: 86%, white solid, m.p.280-282℃. 1 H NMR (600MHz, DMSO-d 6 )δ:2.53(s,3H,CH 3 ), 7.48(m, 3H, phenyl 3'-H, 4'-H, 5'-H), 7.81(d, J=15.6Hz, 1H, COCH=), 7.83(d, J=8.4Hz, 1H, quinazolin-4(3H)-one 8-H), 7.95(m, 2H, phenyl 2'-H, 6'-H), 8.06(d, J=15.6Hz, 1H,=CHPh) ,8.55(d,J=8.4Hz,1H,quinazolin-4(3H)-one 7-H),8.84(s,1H,quinazolin-4(3H)-one 5-H),12.96( br s,1H,NH).ESI-HRMS m / z:C 18 h 15 N 2 o 2 ([M+H] + ) calculated value: 291.1134; measured value: 291.1132.

Embodiment 2

[0127] (E)-6-(3-(2-methoxyphenyl)acryloyl)-2-methylquinazolin-4(3H)-one (compound 2)

[0128] Yield: 56%, yellow solid, m.p.256-258℃. 1 H NMR (600MHz, DMSO-d 6 )δ:2.40(s,3H,CH 3 ),3.92(s,3H,OCH 3 ), 7.05(t, J=7.8Hz, 1H, phenyl 5'-H), 7.14(d, J=7.8Hz, 1H, phenyl 3'-H), 7.47(td, J=7.8, 1.2Hz ,1H,phenyl 4'-H),7.70(d,J=8.4Hz,1H,quinazolin-4(3H)-one 8-H),7.98(d,J=15.6Hz,1H,COCH= ), 8.04 (dd, J = 7.8, 1.2Hz, 1H, phenyl 6'-H), 8.10 (d, J = 15.6Hz, 1H, = CHPh), 8.44 (dd, J = 8.4, 2.4Hz, 1H , quinazoline-4(3H)-one 7-H), 8.79(d, J=2.4Hz, 1H, quinazoline-4(3H)-one 5-H), 12.47(s, 1H, NH) .ESI-HRMS m / z:C 19 h 17 N 2 o 3 ([M+H] + ) calculated value: 321.1239; measured value: 321.1238.

Embodiment 3

[0130] (E)-6-(3-(3-methoxyphenyl)acryloyl)-2-methylquinazolin-4(3H)-one (Compound 3)

[0131] Yield: 41%, white solid, m.p.229-231℃.1 H NMR (600MHz, DMSO-d 6 )δ:2.40(s,3H,CH 3 ),3.85(s,3H,OCH 3 ), 7.05(dd, J=7.8, 2.4Hz, 1H, phenyl 4'-H), 7.39(t, J=7.8Hz, 1H, phenyl 5'-H), 7.49(d, J=7.8Hz ,1H,phenyl 6'-H),7.53(s,1H,phenyl 2'-H),7.70(d,J=8.4Hz,1H,quinazolin-4(3H)-one 8-H) , 7.77(d, J=15.6Hz, 1H, COCH=), 8.05(d, J=15.6Hz, 1H,=CHPh), 8.48(dd, J=8.4, 1.8Hz, 1H, quinazoline-4( 3H)-one 7-H), 8.82(d, J=1.8Hz, 1H, quinazolin-4(3H)-one 5-H), 12.48(s, 1H, NH).ESI-HRMS m / z :C 19 h 17 N 2 o 3 ([M+H] + ) calculated value: 321.1239; measured value: 321.1239.

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Abstract

The invention discloses a chalcone analogue containing 2-methyl-4-oxo-quinazoline-6-base, shown in a general formula (I), wherein the definitions of Ar1 and Ar2 are shown in the description. Besides, the invention further discloses a preparation method and a medical composition of the chalcone analogue containing 2-methyl-4-oxo-quinazoline-6-base. The chalcone analogue containing 2-methyl-4-oxo-quinazoline-6-base, shown in the general formula (I), has an inhibiting effect on cell proliferation of human colonic carcinoma (HCT-116) and human breast cancer (MCF-7), and can be used as an antitumor drug.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, more specifically to chalcone analogues containing 2-methyl-4-oxoquinazolin-6-yl, their preparation methods and their application in antitumor drugs . Background technique [0002] 1,3-diaryl-2-propen-1-ones (1,3-diaryl-2-propen-1-ones), commonly known as chalcone (chalcone), is an important class of secondary metabolites in plants As well as natural precursors of synthetic flavones and isoflavones. Chalcone consists of two aromatic rings, A and B, and an α, β-unsaturated carbonyl system connecting the two rings. In the literature, the aromatic ring connected to the carbonyl group is usually called the A ring, and the aromatic ring connected to the carbon-carbon double bond is called the B ring. Studies have shown that natural or synthetic chalcones have a wide range of pharmacological activities, including antitumor activities [Zhu, C.; Zuo, Y.; Wang, R.; Liang, B.; Yue, X.; Wen, G...

Claims

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Application Information

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IPC IPC(8): C07D239/90C07D403/06C07D405/06C07D409/06C07D401/06A61K31/517A61P35/00
CPCA61K31/517C07D239/90C07D401/06C07D403/06C07D405/06C07D409/06
Inventor 曹胜利许兴智廖蓟丁盼盼马丽张晶晶唐雪
Owner CAPITAL NORMAL UNIVERSITY
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