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Neooxazine compounds and their uses

A compound, 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 simple synthesis method

Inactive Publication Date: 2014-10-29
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the content of natural flavonoids is low, and the stability of 4-chromanone Mannich bases is poor. We have modified the structure of flavonoids and 4-chromanones, designed and synthesized a series of oxazines to overcome The aforementioned disadvantages of natural flavonoids and 4-chromanones

Method used

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  • Neooxazine compounds and their uses
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  • Neooxazine compounds and their uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: 3-Benzyl-2,3,4,6,7,8-hexahydrochromeno[6,7-e][1,3]oxazine

[0027] Dissolve 5 mmol of 7-hydroxychroman in 2 mL of 95% ethanol, add 1.2 mL of 37% formaldehyde aqueous solution, stir for a few minutes, add dropwise 5 mmol of 7-hydroxychroman dissolved in 2-3 mL of 95% ethanol under ice cooling Benzylamine, stirred overnight at room temperature, concentrated and separated by silica gel column chromatography (petroleum ether: ethyl acetate = 30:1) to obtain 3-benzyl-2,3,4,6,7,8-hexahydrochromene [6,7-e][1,3]oxazine as a white solid, yield: 31%. MS m / z (M) 281.35. 1 HNMR (CDCl 3 ):δ2.04(2H,m),2.55(2H,m),3.62(4H,s),3.94(2H,m),5.01(2H,s),6.11(1H,s),6.70(1H, s), 7.10(5H,m).

Embodiment 2

[0028] Example 2: 3-Phenyl-2,3,4,6,7,8-Hexahydrochromeno[6,7-e][1,3]oxazine

[0029] According to the method of Example 1, the white solid 3-phenyl-2,3,4,6,7,8-hexahydrochromene was obtained by reacting 7-hydroxychroman with aqueous formaldehyde and aniline and separated by column chromatography ,7-e][1,3]oxazine, yield: 42%. MS m / z (M) 267.32. 1 HNMR (CDCl 3 ): δ2.04(2H,m),2.55(2H,m), 3.94(2H,m), 4.61(2H,s), 6.00(2H,s), 6.11(1H,s), 6.60(3H, m), 6.70(1H,s), 7.08(2H,m).

Embodiment 3

[0030] Example 3: 3-(2-methylphenyl)-2,3,4,6,7,8-hexahydrochromeno[6,7-e][1,3]oxazine

[0031] According to the method of Example 1, the white solid 3-(2-methylphenyl)-2,3,4,6,7 was obtained by reacting 7-hydroxychroman with formaldehyde aqueous solution and 2-methylaniline and separated by column chromatography ,8-Hexahydrochromeno[6,7-e][1,3]oxazine, yield: 37%. MS m / z (M) 281.35. 1 HNMR (CDCl 3 ): δ2.04(2H,m), 2.35(3H,s), 2.55(2H,m),3.94(2H,m),4.61(2H,s),6.00(2H,s),6.11(1H, s), 6.47(2H,m), 6.70(1H,s), 6.88(2H,m).

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Abstract

The invention belongs to the technical field of medicine, and relates to an oxazine compound and medical application thereof. The oxazine compound and pharmaceutically-applicable salt thereof formed by the addition with acid can be used as a platelet aggregation inhibitor. The structural general formula is shown in the specification. In the structural formula I or II or III or IV or V or VI, R can be independently selected from H, C1-C4 alkyl and benzyl, or substituted or unsubstituted aryl. The synthesis method of the compound provided by the invention is simple and is applicable to industrial production; the compound is more stable in comparison with natural analogs; and biological activity tests show that the compound has analgesic, antiphlogistic and anticoagulant activities. Thus, the compound is a platelet aggregation inhibitor.

Description

[0001] This application is a divisional application filed by Shenyang Pharmaceutical University on February 9, 2009 with the application number 200910010321.9 and the title of the invention "New oxazine compounds and their anti-platelet aggregation application". technical field [0002] The invention belongs to the technical field of medicine, and relates to oxazine compounds and their anti-platelet aggregation application. technical background [0003] 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. [0004] Platelets are produced by the lysis of mature megakaryocytes in the bone marrow. The newly formed platelets are large in size, have...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04A61K31/5365A61P7/02
Inventor 胡春黄二芳王颖兰惠瑜刘晓平宋爱华
Owner SHENYANG PHARMA UNIVERSITY
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