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Novel oxazine compound and use for preventing platelet aggregation

A compound and oxazine 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: 2013-01-23
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. Modified, designed and synthesized a series of oxazines to overcome the above-mentioned shortcomings of natural flavonoids and 4-chromanones

Method used

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  • Novel oxazine compound and use for preventing platelet aggregation
  • Novel oxazine compound and use for preventing platelet aggregation
  • Novel oxazine compound and use for preventing platelet aggregation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: 9-phenyl-4,8,9,10-tetrahydroflavone[8,7-e][1,3]oxazine

[0024] Mix 1.2mL 37% formaldehyde aqueous solution with 5mmol aniline dissolved in 2-3mL 95% ethanol, heat to reflux and stir for a few minutes, then add 5mmol 7-hydroxyflavone dissolved in 10mL 95% ethanol, heat to reflux and stir overnight. After cooling, a large amount of white precipitate was precipitated, which was filtered by suction, and finally recrystallized by ethanol to obtain white crystals with a yield of 44%. MS m / z (M): 355.39. 1 HNMR (CDCl 3 ): δ4.61 (2H, s), 6.00 (2H, s), 6.40 (1H, d), 6.60 (3H, m), 6.71 (1H, s), 7.08~7.34 (8H, m). δ

Embodiment 2

[0025] Example 2: 9-Benzyl-4,8,9,10-tetrahydroflavone[8,7-e][1,3]oxazine

[0026] According to the preparation method provided in Example 1, the compound is obtained by reacting 7-hydroxy-flavone with aqueous formaldehyde and benzylamine. Yield: 47%. MS m / z (M): 369.41. 1 HNMR (CDCl 3 ): δ3.62 (4H, s), 5.01 (2H, s), 6.40 (1H, d), 6.60 (3H, m), 6.71 (1H, s), 7.06-7.21 (8H, m).

Embodiment 3

[0027] Example 3: 9-(2-methylphenyl)-4,8,9,10-tetrahydroflavone[8,7-e][1,3]oxazine

[0028] According to the preparation method provided in Example 1, the compound is obtained by reacting 7-hydroxy-flavone with aqueous formaldehyde and 2-methylaniline. Yield: 38%. MS m / z (M): 369.41. 1 HNMR (CDCl 3 ): δ2.35(3H, s), 4.61(2H, s), 6.00(2H, s), 6.40(1H, d), 6.47(2H, m), 6.71(1H, s), 6.89(2H, m), 7.14-7.34 (6H, m).

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Abstract

The invention pertains to the field of medical technology, relating to an oxazine compound and a medical application thereof; the oxazine compound and an oxazine salt obtained from an addition reaction of pharmaceutically-applicable oxazine acid can be used as a platelet aggregation inhibitor; the oxazine compound has a structural formula shown as above; in a structural formula I and a structural formula II, X can be independently chosen from CH2 and C=0, R1 can be independently chosen from H and a substituted or un-substituted aromatic base, R2 can be independently chosen from H or a substituted or un-substituted aromatic base, and R3 can be independently chosen from H, alkyl group with one to four carbon atoms, benzyl or substituted or un-substituted aromatic base. The oxazine compound has simple synthetic method, adapts to industrialized production and is more stable when compared with natural analogues. Shown by biological activity assay, the oxazine compound has the functions of analgesia, anti-inflammatory and antithrombin activity and is a platelet aggregation inhibiting medicament.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to oxazine 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, aggregation and releas...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04A61K31/5365A61K31/5383A61P7/02A61P29/00
Inventor 胡春刘晓平王颖刘洋黄二芳宋爱华
Owner SHENYANG PHARMA UNIVERSITY
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