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Novel isoflavone nicotinic acid ester derivatives, preparing method and use thereof

A technology of nicotinic acid isoflavone ester and isoflavone ester, which is applied in the field of chemical compounds and can solve problems such as failure to effectively solve problems

Inactive Publication Date: 2008-07-02
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, none of the techniques reported in the above literature can effectively solve the problem.

Method used

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  • Novel isoflavone nicotinic acid ester derivatives, preparing method and use thereof
  • Novel isoflavone nicotinic acid ester derivatives, preparing method and use thereof
  • Novel isoflavone nicotinic acid ester derivatives, preparing method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Preparation of 4',5-di-hydroxy-7-nicotinic acid isoflavone ester (code 101) and 5-hydroxy-4',7-di-nicotinic acid isoflavone ester (code 102):

[0089] The 0.01mol 4′,5,7-trihydroxyisoflavone 1 was reacted with 0.03mol niacin in 10ml thionyl chloride at 72℃ for 9 hours, poured into an ice water bath, and extracted with ethyl acetate 3 times. Drying with sodium sulfate and then column chromatography with ethyl acetate: petroleum ether = 1:3 to obtain the target product 4',5-di-hydroxy-7-nicotinic acid isoflavone ester 2 with a yield of 45.2% and 5-hydroxy- 4',7-Di-nicotinic acid isoflavone ester 3, the yield is 52.6%. The relevant data are as follows:

[0090] 4',5-Di-hydroxy-7-nicotinic acid isoflavone 2 (code 101) MS (EI, 70ev) m / z: 375; 1 H NMR(300MHz, CDCl 3 ): 6.29 (2H, s), 6.98 (2H, d, J = 8.1 Hz), 7.12 (2H, d, J = 8.1 Hz), 7.48 (1H, s), 7.58-9.02 (4H, m), 9.50 (1H, s), 12.04 (1H, s); Anal.Calcd.forC 21 H 13 NO 6 : C, 67.20, H, 3.49, N 3.73; Found C, 67.19, H, 3.50, N 3...

Embodiment 2

[0092] Preparation of 4',5-di-methoxy-7-nicotinic acid isoflavone ester (code number 103):

[0093] Dissolve 0.03mol methyl iodide and 0.01mol 4′,5-di-hydroxy-7-nicotinic acid isoflavone ester 2 in 25ml acetone, add 10g catalyst K 2 CO 3 And react at 60°C for 4 hours to obtain the target product 4',5-di-methoxy-7-nicotinic acid isoflavone ester. The relevant data are as follows:

[0094] MS (EI, 70ev) m / z: 403; Anal.Calcd.for C 23 H 17 NO 6 : C, 68.48, H, 4.25, N3.47; Found C, 68.51, H, 4.21, N3.52.

Embodiment 3

[0096] Preparation of 4',5-di-ethoxy-7-nicotinic acid isoflavone ester (code number 104):

[0097] Using 0.03 mol of bromoethane instead of methyl iodide, the compound 4',5-di-ethoxy-7-nicotinic acid isoflavone ester can be obtained according to the operation of Example 2. The relevant data are as follows:

[0098] MS (EI, 70ev) m / z: 43 1; Anal.Calcd.for C 25 H21 NO 6 : C, 69.60, H, 4.91, N3.25; Found C, 69.33, H, 4.81, N3.22.

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Abstract

The invention relates to a new ramification containing nicotinic acid isoflavone ester and a preparation method and application thereof. Being proved by pharmacological tests, the new ramification containing nicotinic acid isoflavone ester of the invention has functions of antidiabetics, antiatheroscloresis, decreasing blood pressure, anticancer, calmness and antianxiety, antibiosis and antivirus with different degrees and has relatively small toxicity. Therefore, the new ramification containing nicotinic acid isoflavone ester of the invention and salt thereof can be used for preparing medicines of antidiabetics, antiatheroscloresis, decreasing blood pressure, anticancer, calmness and antianxiety, antibiosis and antivirus; meanwhile, the invention has relatively small toxicity and easy preparation method, is convenient for industrial production and can meet the needs of medicine field. The compound of the invention has the advantages of high curative effect, low toxicity, etc.

Description

Technical field [0001] The present invention relates to a compound, especially a new isoflavone nicotinic acid-containing derivative and its preparation method and use. The compound has lowering blood sugar, lowering blood lipid, lowering blood pressure, anti-cancer, sedation and anti-anxiety, antibacterial, antibacterial, antibacterial and antibacterial properties. Virus effect. Background technique [0002] Isoflavone compounds are widely distributed in the plant kingdom. Isoflavone compounds have various physiological and pharmacological effects such as dilation of coronary arteries, anti-inflammatory, antibacterial, anti-tumor, lowering blood pressure, prevention and treatment of tracheitis, and liver protection. However, the biological activity of isoflavone compounds is weak, which limits their application in the field of medicine. In order to enhance its effect, literature (Yan Bingshuang, et al. Chinese Journal of Medicinal Chemistry, 1995, 5(1):44) reported that imidazol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12A61K31/453A61P35/00A61P3/08A61P3/06A61P31/04A61P31/12A61P25/22
Inventor 廖端芳郑兴朱炳阳
Owner NANHUA UNIV
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