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6-cinnamon acyl-2H-benzo [b] [1, 4] oxazine-3 (4H)-ketone compound and application thereof

Technology of a compound, oxazine, applied in the field of chalcone derivatives of benzoxazine

Inactive Publication Date: 2014-04-30
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 6-cinnamoyl-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives are based on the basic structure of chalcone, and introduce a broad-spectrum antibacterial and anti-inflammatory , anti-virus, anti-tumor, and inhibitory protein methyltransferase benzoxazinone structure, which realizes further modification of drug molecules, which is conducive to improving the physical and chemical properties of drugs. After searching, there are no relevant literature and patent reports.

Method used

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  • 6-cinnamon acyl-2H-benzo [b] [1, 4] oxazine-3 (4H)-ketone compound and application thereof
  • 6-cinnamon acyl-2H-benzo [b] [1, 4] oxazine-3 (4H)-ketone compound and application thereof
  • 6-cinnamon acyl-2H-benzo [b] [1, 4] oxazine-3 (4H)-ketone compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: Intermediate 1 namely: the synthesis of 6-acetyl-2H-benzo[b][1,4]oxazin-3(4H)-one

[0026]

[0027] Add 3.82 grams of 2H-benzo[b][1,4]oxazin-3(4H)-one and 13.33 grams of aluminum chloride in a 250-ml round-bottomed flask, and 100 milliliters of anhydrous dichloromethane, and react in an ice bath After 30 minutes, 2.04 g of acetic anhydride was added slowly. Heated to reflux, and the reaction was detected by TLC until the raw material was completely consumed, and the reaction time was 5 hours. The reacted mixture was diluted with water and filtered, and the filtrate was washed twice with 100 ml of saturated sodium bicarbonate solution and once with water, and the resulting solution was dried over sodium sulfate and concentrated under reduced pressure to obtain a crude product, which was recrystallized with methanol to obtain a pure product, the product The rate is 51%.

[0028] Molecular formula: C 10 h 9 NO 3

[0029] Molecular weight: 191.18

[...

Embodiment 2

[0032] Embodiment 2: Compound 1 namely: the synthesis of 6-cinnamoyl-2H-benzo[b][1,4]oxazin-3(4H)-ketone

[0033]

[0034] Add 287 mg of 6-acetyl-2H-benzo[b][1,4]oxazin-3(4H)-one and 191 mg of benzaldehyde, 120 mg of sodium hydroxide, 40 One milliliter of anhydrous methanol was heated to reflux, and the reaction was detected by TLC until the raw material was completely consumed, and the reaction time was 12 hours. The reaction mixture was cooled to room temperature and filtered to obtain 6-cinnamoyl-2H-benzo[b][1,4]oxazin-3(4H)-one (231 mg) with a yield of 55.2%.

[0035] Molecular formula: C 17 h 13 NO 3

[0036] Molecular weight: 279.29

[0037] Appearance: yellow solid

[0038] Melting point: 245-247°C.

[0039] The NMR data are as follows:

[0040] 1H NMR (DMSO, 400MHz): δ=10.87(s, 1H, NH), 7.91(dd, J1=2.04, J2=8.36Hz, 1H, CH), 7.46-7.89(m, 8H, ArH), 7.10( d, J=8.36Hz, 1H, CH), 4.72 (s, 2H, CH2).13C NMR (DMSO, 100MHz): δ=187.82, 164.63, 147.89, 144.04, 135.17, ...

Embodiment 3

[0045] Embodiment 3: Compound 2 namely: the synthesis of 6-piperonylacryloyl-2H-benzo[b][1,4]oxazin-3(4H)-one

[0046]

[0047] Add 287 mg of 6-acetyl-2H-benzo[b][1,4]oxazin-3(4H)-one, 270 mg of piperonal, 120 mg of sodium hydroxide in a 100 ml round bottom flask, 40 One milliliter of anhydrous methanol was heated to reflux, and the reaction was detected by TLC until the raw material was completely consumed, and the reaction time was 12 hours. The reaction mixture was cooled to room temperature and filtered to obtain 6-piperonylacryloyl-2H-benzo[b][1,4]oxazin-3(4H)-one (219 mg) with a yield of 45.2%.

[0048] Molecular formula: C 18 h 13 NO 5

[0049] Molecular weight: 323.30

[0050] Appearance: yellow solid

[0051] Melting point: 267-268°C.

[0052] The NMR data are as follows:

[0053] 1 H NMR (DMSO, 300MHz): δ=10.86(s, 1H, NH), 7.91(dd, J 1 =2.1,J 2 =8.4Hz, 1H, CH), 6.98-7.77(m, 6H, ArH), 7.08(d, J=8.4Hz, 1H, CH), 6.11(s, 2H, CH 2 ), 4.70 (s, 2H, CH 2 ). ...

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Abstract

The invention discloses a 6-cinnamon acyl-2H-benzo [b] [1, 4] oxazine-3 (4H)-ketone derivative and application thereof, wherein a structural general formula of the derivative is shown in Formula (I), and Ar in the formula represents an aryl. Pharmacological experiments show that the compound provided by the invention has an obviously inhibiting effect on the proliferation of lung carcinoma cells A549, and indicate that a chalcone derivative containing benzoxazine ketone disclosed by the invention has development prospects in clinical applications and has important values in the exploitation of anti-tumor drugs.

Description

technical field [0001] The present invention relates to a chalcone derivative of benzoxazine and its application, in particular to a 6-cinnamoyl-2H-benzo[b][1,4]oxazin-3(4H)-ketone Compound and its application in the preparation of antitumor drugs. Background technique [0002] The chalcone structure is the main pharmacophore of many drugs and is a synthon of some drug molecules and natural product molecules. For example, the chalcone compounds described in patents CN102397269 and CN101759544 have good applications in the preparation of anti-inflammatory drugs and drugs for the treatment of inflammation-related diseases; at the same time, in patent CN103382195, benzopyranchalcone compounds have an effect on the inflammatory factor iNOS , TNF-α or IL-4 have inhibitory effect and can be used to treat inflammations such as osteoarthritis, rheumatoid arthritis or asthma. The chalcone compound described in the patent CN103483211 has antibacterial synergistic effect. The chalco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/36C07D413/06A61K31/538A61P35/00
CPCC07D265/36C07D413/06
Inventor 赵宝祥苗俊英周学文马汉林
Owner SHANDONG UNIV
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