Fluoro isoflavone containing derivative, monufacturing method and its use

A technology of difluoromethoxy isoflavones and derivatives, which is applied in the field of fluorine-containing isoflavone derivatives, and can solve problems such as technology failure to effectively solve problems

Inactive Publication Date: 2004-02-18
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the technology reported in the above literature cannot effectively solve the problem

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] 4', 5-di-hydroxy-7-difluoromethoxy isoflavone (code 101) and 5-hydroxy-4', 7-di-difluoromethoxy isoflavone (code 102):

[0068] 0.01mol4', 5,7-trihydroxyisoflavone 1 is mixed with 0.03molHCF in 10ml concentration of 40% dioxane and sodium hydroxide aqueous solution at 72°C 2 Cl was reacted for 9 hours, extracted 3 times with ethyl acetate, dried over anhydrous sodium sulfate, and then column chromatographed with ethyl acetate:petroleum ether=1:3 to obtain the target product 4',5-di-hydroxy-7-di The yield of fluoromethoxy isoflavone 2 is 45.2% and that of 5-hydroxy-4',7-bis-difluoromethoxy isoflavone 3 is 52.6%.

[0069] The relevant data are as follows: 4', 5-di-hydroxy-7-difluoromethoxy isoflavone 2 (code 101) MS (EI, 70ev) m / z: 320; IRυ max (cm -1 , KBr): 1662 (C=O), 3319, 3528 (OH); 1 H NMR (300MHz, CDCl 3 ): 6.599 (1H, d, J = 2.4), 6.820 (2H, d, J = 12.0), 6.867 (1H, d, J = 2.4), 7.371 (2H, d, J = 12.0), 7.427 (1H, t, J = 72.8), 8.244 (1H, s), 9.550 (1H, s), 12...

Embodiment 24

[0071] Embodiment 24', the preparation of 5-two-methoxy-7-difluoromethoxy isoflavone (code name 103)

[0072] 0.03mol methyl iodide and 0.01mol 4', 5-two-hydroxyl-7-difluoromethoxy isoflavone 2 were dissolved in 25ml of acetone, and 10 grams of catalyst K was added 2 CO 3 , reacted at 60°C for 4 hours to obtain the target product 4', 5-bis-methoxy-7-difluoromethoxy isoflavone.

[0073] The relevant data are as follows: MS (EI, 70ev) m / z: 348; IRυ max (cm -1 , KBr): 1637 (C=O); 1 H NMR (300MHz, CDCl 3 ): 3.834 (3H, s), 3.970 (3H, s), 6.546 (1H, d, J=2.1), 6.642 (1H, t, J=72.4), 6.724 (1H, d, J=2.1), 6.940 (2H, d, J=8.7), 7.472 (2H, d, J=8.7), 7.811 (1H, s); 19 F NMR (300MHz) - 82.150 (d, J=72.4).

Embodiment 3

[0074] Example 3 4', the preparation of 5-bis-ethoxy-7-difluoromethoxy isoflavone (code 104)

[0075] Replace methyl iodide with 0.03mol bromoethane according to the operation of Example 2 to obtain compound 4', 5-bis-ethoxy-7-difluoromethoxy isoflavone. The relevant data are as follows: MS (EI, 70ev) m / z: 376; IRυ max (cm -1 , KBr): 1613 (C=O); 1 H NMR (300MHz, CDCl 3 ): 1.386-1.572 (6H, m), 4.023-4.181 (4H, m), 6.525 (1H, d, J=2.4), 6.628 (1H, t, J=72.6), 6.699 (1H, d, J= 2.4), 6.931 (2H, d, J=8.4), 7.436 (2H, d, J=8.4), 7.780 (1H, s); 19 F NMR (300MHz)-82.085 (d, J=72.6).

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Abstract

A fluoric isoflavone derivative and its preparing process are disclosed. Said derivative can be used to prepare the medicines for treating cancer, hypertension, hyperglycemia, dysphoria and bacterialand viral diseases. Its advantages are high curative effect and low poison.

Description

technical field [0001] The present invention relates to a class of fluorine-containing isoflavone derivatives, a production method and its application, in particular to a class of fluorine-containing isoflavones with anti-cancer, antihypertensive, hypoglycemic, sedative, anti-anxiety, antibacterial and antiviral effects derivative. Background technique [0002] Isoflavones are widely distributed in the plant kingdom. Isoflavones have various physiological activities and pharmacological effects such as dilating coronary arteries, anti-inflammation, antibacterial, anti-tumor, lowering blood pressure, preventing and treating tracheitis, and protecting the liver. However, the biological activity of isoflavones is weak, which limits their application in the field of medicine. In order to enhance its effect, literature (Yan Bingshuang, etc. Chinese Journal of Medicinal Chemistry, 1995, 5 (1): 44) reported that imidazole, amino, alkyl and other groups were introduced into the basi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/352A61P3/10A61P9/12A61P25/20A61P25/22A61P31/04A61P31/12A61P35/00C07D311/30
Inventor 卿凤翎郑兴
Owner DONGHUA UNIV
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