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Flavone derivative, preparation method and application

A technology of derivatives and flavonoids, applied in the field of flavonoid derivatives and preparation, can solve problems such as visual disturbance, headache and facial flushing

Inactive Publication Date: 2008-03-26
TOPHARMAN SHANGHAI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to clinical side effects such as headache, facial flushing, and visual disturbance

Method used

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  • Flavone derivative, preparation method and application
  • Flavone derivative, preparation method and application
  • Flavone derivative, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1 3,7-diacetoxy-5-hydroxy-4'-methoxy-8-(3,3-dimethylpropenyl)flavone (TPN1306)

[0064]

[0065] Add 0.200 g of icariin to a 100 mL flask, dissolve it with 27 mL of anhydrous pyridine, add 0.127 mL of acetic anhydride, stir at room temperature for 3 h, then add 50 mL of saturated NaHCO 3 The aqueous solution was extracted three times with ethyl acetate (50 mL each time), the ethyl acetate layer was washed twice with saturated brine (50 mL each time), the organic phase was dried over anhydrous sodium sulfate, concentrated by filtration, and separated by silica gel column chromatography ( Eluent: petroleum ether / ethyl acetate=3:1) to obtain the target compound (0.174 g, 71%). 1 HNMR (CDCl 3 ): δ1.69 (3H, s, H-4″), 1.73 (3H, s, H-5″), 2.35 (3H, s, C 3 -OAc), 2.37 (3H, s, C 7 -OAc), 3.42 (2H, d, J=6.3Hz, H-1″), 3.90 (3H, s, OCH 3 ), 5.13 (1H, t, J=6.3Hz, H-2″), 6.58 (1H, s, H-6), 7.02 (2H, d, J=9.0Hz, H-3′, 5′), 7.52 (2H, d, J=9.0Hz, H-2', 6'), 12.15 (1H, s,...

Embodiment 2

[0066] Example 2 3,7-diacetoxy-5,4'-dimethoxy-8-(3,3-dimethylpropenyl)flavone (TPN1308)

[0067]

[0068] Add 0.010 g of the compound of Example 1 to a 5 mL flask, dissolve it in 1.1 mL of DMF, add 0.006 g of potassium carbonate and 0.014 mL of methyl iodide successively, stir at room temperature for 3 h, add 20 mL of saturated NH 4 Cl aqueous solution was extracted three times with ethyl acetate (20 mL each time), the ethyl acetate layer was washed twice with saturated brine (50 mL each time), dried over anhydrous sodium sulfate, concentrated by filtration, and separated by silica gel column chromatography ( Eluent: petroleum ether / ethyl acetate=4:1) to obtain the title compound (0.009 g, 87%). 1 H-NMR (CDCl 3 ): δ1.69 (3H, s, 3-CH 3 ), 1.73 (3H, s, 3-CH 3 ), 2.35 (3H, s, COCH 3 ), 2.36 (3H, s, COCH 3 ), 3.45 (2H, d, J=6.4Hz, H-1), 3.88 (3H, s, OCH 3 ), 3.93 (3H, s, 4'-OCH 3 ), 5.14 (1H, br t, J=6.4Hz, H-2), 6.55 (1H, s, H-6), 7.00 (2H, d, J=8.8Hz, H-3′, H-5′ ), 7....

Embodiment 3

[0069] Example 3 3,7-diacetoxy-5-ethoxy-4'-methoxy-8-(3,3-dimethylpropenyl)flavone (TPN1338)

[0070]

[0071] 0.010 gram of Example 1 compound, 1.1 mL of DMF, 0.006 gram of K 2 CO 3 , 0.004 g of KI and 0.017 mL of bromoethane were successively added into a 5 mL round bottom flask, and stirred at room temperature for 6.5 h. After the reaction was completed, 30 mL of saturated NH 4 Cl solution, extracted with EtOAc (3×30mL), the organic phase was washed with saturated brine (2×20mL), washed with anhydrous Na 2 SO 4 After drying, it was concentrated by filtration and separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=3:1) to obtain the target compound (0.006 g, 57%). 1 H NMR (CDCl 3 ): δ1.47 (3H, t, J=6.9Hz, C 5 -OCH 2 CH 3 ), 1.69 (3H, s, H-4″), 1.76 (3H, s, H-5″), 2.33 (3H, s, C 3 -OAc), 2.43 (3H, s, C 7 -OAc), 3.58 (2H, d, J=6.6Hz, H-1″), 3.88 (3H, s, C 4 '-OCH 3 ), 4.13 (2H, q, J=6.9Hz, C 5 -OCH 2 CH 3 ), 5.20 (1H, t, J=6.6...

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Abstract

The present invention relates to flavone derivatives in the structure as shown, and their preparation process and intermediate. These compounds have excellent PDE5 inhibiting activity, and may be applied in treating sexual disorder and vasoconstriction related diseases.

Description

technical field [0001] The invention relates to organic synthesis, more specifically to a class of flavonoid derivatives, a preparation method and application. Background technique [0002] Sildenafil citrate (sildenafil) was developed by Pfizer and launched in March 1998 as the first oral drug for the treatment of ED. However, there are side effects such as headache, facial flushing, and visual disturbance clinically. PDE5 inhibitory active substances with both high activity and high selectivity are currently a hot spot in the research and development of drugs for the prevention and treatment of sexual dysfunction. [0003] Epimedium is a commonly used ingredient in the prescription of traditional Chinese medicine tonic and tonic. There have been many studies on the chemical constituents and pharmacological effects of the crude drug Epimedium or its extracts. Dozens of compounds have been isolated and identified from it, including icariin (5-hydroxy-4'-methoxy-8-(3,3-dim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D407/12A61K31/352A61K31/5355A61K31/496A61P15/10C07D303/00C07D311/00
CPCC07D311/74C07D405/06A61P9/00A61P9/10A61P9/12A61P11/00A61P13/08A61P15/00A61P15/10A61P27/06A61P31/00
Inventor 张树军郭洪利陈新建棘玉荣刘正赖庆林年亦丰沈敬山
Owner TOPHARMAN SHANGHAI
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