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Novel oxazine compound and use for preventing platelet aggregation
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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: 2009-07-22
SHENYANG PHARMA UNIVERSITY
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[0006] However, the content of natural flavonoids is low, and the stability of 4-chromanone Mannich bases is poor. We have modified the structures of flavonoids and 4-chromanones, and designed and synthesized a series of oxazines to overcome The aforementioned disadvantages of natural flavonoids and 4-chromanones
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Embodiment 1
[0025] Example 1: 3-Benzyl-2,3,4,6,7,8-hexahydrochromeno[6,7-e][1,3]oxazine
[0026] Dissolve 5mmol of 7-hydroxychroman in 2mL of 95% ethanol, add 1.2mL of 37% formaldehydeaqueous solution, stir for a few minutes, add dropwise 5mmol of benzylamine dissolved in 2-3mL of 95% ethanol under ice-cooling, room temperature Stir overnight, concentrate and separate by silica gelcolumn chromatography (petroleumether: ethyl acetate = 30:1) to give 3-benzyl-2,3,4,6,7,8-hexahydrochromeno[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
[0027] Example 2: 3-phenyl-2,3,4,6,7,8-hexahydrochromeno[6,7-e][1,3]oxazine
[0028] According to the method of Example 1, the white solid 3-phenyl-2,3,4,6,7,8-hexahydrochromeno[6 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
[0029] Example 3: 3-(2-methylphenyl)-2,3,4,6,7,8-hexahydrochromeno[6,7-e][1,3]oxazine
[0030] 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 aqueous formaldehyde 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 pertains to the filed 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 with a structural formula shown as follow; in structural formulas I-VI, 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 activityassay, 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. technical background [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...
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