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Furo[2,3-h] chromene compound and use for preventing platelet aggregation

A 3-h, compound technology, applied in the field of medicine, can solve the problems of poor stability and low content of natural flavonoids, and achieve the effect of a simple synthesis method

Inactive Publication Date: 2013-05-15
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the content of natural flavonoids is low, and the stability of 4-chromanone Mannich bases is poor. We modified the structures of flavonoids and 4-chromanones, designed and synthesized a series of furo[2,3- h] chromene compounds to overcome the above-mentioned shortcomings of natural flavonoids and 4-chromanones

Method used

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  • Furo[2,3-h] chromene compound and use for preventing platelet aggregation
  • Furo[2,3-h] chromene compound and use for preventing platelet aggregation
  • Furo[2,3-h] chromene compound and use for preventing platelet aggregation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: 8-benzoyl-9-methylfuro[2,3-h]-4-chromanone

[0023] Mix 3mmol 7-hydroxy-8-acetyl-4-chromanone, 3mmol α-chloroacetophenone, 30mmol anhydrous potassium carbonate, and 50mL dry acetone, stir and reflux for 7 hours. After cooling, filter with suction, remove acetone by rotary evaporation, add 30 mL of ethyl acetate, wash with 10 mL of water and 10 mL of saturated sodium chloride aqueous solution in turn, dry, and remove ethyl acetate by rotary evaporation. Separation by column chromatography (oil ether: ethyl acetate = 8:1) gave a white solid. Yield 42%, MS m / z (M): 306.31. 1 H-NMR (d 6 -DMSO): δ1.94 (3H, s), 2.97 (2H, t), 4.13 (2H, t), 7.06 (1H, d, J=8.88Hz), 7.45-7.54 (3H, m), 7.71 ( 1H, d, J = 8.91 Hz), 7.81 (2H, m).

Embodiment 2

[0024] Example 2: 8-(4-methylbenzoyl)-9-methylfuro[2,3-h]-4-chromanone

[0025] According to the method in Example 1, a white solid was obtained by reacting 7-hydroxy-8-acetyl-4-chromanone and 4-methyl-α-chloroacetophenone with a yield of 38%. MS m / z (M): 320.34. 1 H-NMR (d 6 -DMSO): δ1.95 (3H, s), 2.35 (3H, s), 2.97 (2H, t), 4.13 (2H, t), 7.06 (1H, d, J=8.92Hz), 7.25 (2H, dd, J = 1.80, 8.88 Hz), 7.69-7.71 (3H, m).

Embodiment 3

[0026] Example 3: 8-(4-chlorobenzoyl)-9-methylfuro[2,3-h]-4-chromanone

[0027] According to the method in Example 1, a white solid was obtained by reacting 7-hydroxy-8-acetyl-4-chromanone and 4-chloro-α-chloroacetophenone with a yield of 32%. MS m / z (M): 340.76. 1 H-NMR (d 6 -DMSO): δ1.94 (3H, s), 2.97 (2H, t), 4.13 (2H, t), 7.06 (1H, d, J=8.91Hz), 7.46 (2H, dd, J=1.80, 8.88 Hz), 7.71-7.75 (3H, m).

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Abstract

The invention pertains to the field of medical technology and relates to a furo [2, 3-h] chromene compound and an application thereof for inhibiting platelet aggregation; the furo [2, 3-h] chromene compound, pharmaceutically-acceptable salt, or stereo-isomers and pre-drugs of the furo [2, 3-h] chromene compound, as well as pharmaceutical compatibility acceptable carriers or diluents of the furo [2, 3-h] chromene compound can be used as platelet aggregation inhibitors. The structural formula of the furo [2, 3-h] chromene compound is as shown above, wherein, X can be chosen from CH2 or C=O, R1 can be independently chosen from H or a substituted or un-substituted aromatic base, R2 can be independently chosen from H or a substituted or un-substituted aromatic base, and R can be independently chosen from H, alkyl group with one to four carbon atoms, chlorine, bromine, fluorin, methoxyl, nitryl or hydroxyl. The furo [2, 3-h] chromene compound has simple synthetic method, adapts to industrialized production and is more stable compared with natural analogues. Shown by biological activity assay, the furo [2, 3-h] chromene compound has antithrombin activity and is a platelet aggregation inhibiting drug.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to furo[2,3-h]chromene compounds and their anti-platelet aggregation application. Background technique [0002] Clinical studies have shown that common cardiovascular and cerebrovascular diseases such as hypertension, diabetes, angina pectoris, myocardial infarction, cerebral infarction and cerebral hemorrhage are all related to changes in platelet function and abnormal blood rheology (Tianjin Medicine, 1992, 20 (11):684). Therefore, preventing platelet aggregation is of great significance. [0003] Platelets are produced by the lysis of mature megakaryocytes in the bone marrow. The newly formed platelets are large in size, have the ability to synthesize proteins, have strong adhesion, are easy to aggregate and release reactions, and have hemostatic function. At present, it is believed that the physiological activities of platelets mainly include three aspects: adhesion, aggregatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04A61K31/352A61P7/02A61P7/00A61P9/10A61P11/00A61P17/02A61P19/02A61P1/00A61P25/28A61P27/02A61P43/00
Inventor 胡春刘晓平洪秀云黄二芳王颖王世辉金丽萍宋爱华詹华强董婷霞
Owner SHENYANG PHARMA UNIVERSITY
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