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6,8-substituted naringenin derivative and application thereof

A Derivative, Naringenin Technology

Active Publication Date: 2013-04-03
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Codeine phosphate is currently the most commonly used drug in clinical treatment of cough, but the drug is clinically addictive

Method used

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  • 6,8-substituted naringenin derivative and application thereof
  • 6,8-substituted naringenin derivative and application thereof
  • 6,8-substituted naringenin derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: 8-n-propylnaringenin (8-Propyl-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one).

[0050]

[0051] 1 g of 8-allylnaringenin (compound 18) was dissolved in 100 ml of ethanol. Add 10% Pd / C 0.5g hydrogenation at normal pressure for 20 hours. After suction filtration, the filtrate was concentrated and purified by silica gel column chromatography with petroleum ether: ethyl acetate = 2:1 to obtain 0.4 g of a yellow solid. The melting point is 195-197°C; thin-layer chromatography was carried out with petroleum ether: ethyl acetate = 1:1 as the developing solvent, Rf = 0.6; mass spectrum LRMS M-H = 313.4, HPLC purity = 99%, yield = 40%.

[0052] NMR: 1 H-NMR (400MHz, DMSO-d6): δ0.872 (3H, t, J=7.2Hz; H-3″), δ1.441 (2H, q, J=7.2 Hz, H-2″), δ2 .415(2H,t,J=8.4Hz,H-1〃),δ2.651(1H,dd,J 1 =16.8Hz,J 2 =2.8Hz,H-3a),δ3.213(1H,dd,J 1 =12.8Hz, J 2 =16.8Hz,H-3b),δ5.386(1H,dd,J 1 =12.8Hz,J 2 =2.8Hz, H-2), δ5.945(1H, s, H-6), δ6.788 (2H, d, J=8.8 Hz, H-3′, H...

Embodiment 2

[0054] Example 2: 6-n-propylnaringenin (6-Propyl-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one).

[0055]

[0056] 1 g of 6-allylnaringenin (compound 19) was dissolved in 100 ml of ethanol. Add Pd / C 0.2g and hydrogenate at normal pressure for 20 hours. After suction filtration, the filtrate was concentrated and purified by silica gel column chromatography with petroleum ether: ethyl acetate = 3:1 to obtain 0.4 g of a light yellow solid. The melting point is 173-175°C; thin-layer chromatography was carried out with petroleum ether: ethyl acetate = 1:1 as developing solvent, Rf = 0.6; mass spectrum M-H = 313.2, HPLC purity = 96%, yield = 13%.

[0057] NMR: 1 H-NMR (400MHz, DMSO-d6): δ0.822 (3H, t, J=7.2Hz; H-3″), δ1.417 (2H, q, J=7.2Hz, H-2″), δ2 .397(2H,t,J=7.2Hz,H-1〃),δ2.733 (1 H,dd,J 1 =17.2Hz,J 2=3.2Hz, H-3a), δ3.162(1H,dd,J 1 =12.4Hz,J 2 =16.8Hz, H-3b), δ5.408(1H,dd,J 1 =12.4Hz,J 2 =2.8Hz,H-2),δ5.976(1H, s,H-8),δ6.801 (2H,d,J=8.4Hz,H-3′,H-5′),δ7.304...

Embodiment 3

[0059] Example 3: 6-bromo-8-allylnaringenin (8-Allyl-6-bromo-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one) .

[0060]

[0061] Dissolve 0.7 g of 8-allylnaringenin (compound 18) in 50 ml of carbon tetrachloride (CCl 4 ), add 2 ml dimethylformamide, add 1.05eq N-bromosuccinimide (NBS), and heat to reflux for 5 hours. After cooling and concentrating, the sample was directly mixed and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain 0.48 g of a light yellow solid. Melting point is 203-205°C; TLC with petroleum ether: ethyl acetate = 3:1 as developing solvent, Rf = 0.6; mass spectrum LRMS: M-H = 391.2, 389.2; HPLC purity = 89.22%, yield 55% .

[0062] NMR: 1 H-NMR(400MHz,DMSO-d6):δ2.82(1H,dd,J 1 =2.8 Hz, J 2 =17.2Hz, H-3b), δ3.275(3H,m,H-1″,H-3a),δ4.901(2H,m,H-3″),δ5.478(1H,dd, J 1 =2.8Hz,J 2 =12.8Hz,H-2),δ5.795(1H,m,H-2〃),δ6.800(2H,t,H-3′,H5′),δ7.305(2H,d,J= 8.8Hz, H-2′, H-6′), δ9.553(1H, s, H-4′OH), δ10.334(1...

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Abstract

The invention discloses a series of 6,8-substituted naringenin derivatives which are modified by the naringenin as a lead compound and remarkably improve the functional biological activity of a respiratory system, and pharmaceutically acceptable salt of the derivative, and further discloses a preparation method of the derivates and the application in preparing cough relieving medicines. The derivate has the structure formula (1), wherein A6 and A8 are respectively selected from H, halogen, hydroxyl, alkyl with 1-3 carbon atoms and straight chain alkenyl, alcohol group, formyl or carboxylic acid group with 2-3 carbon atoms. Tests show that the derivate has a remarkable cough relieving function, is simple and stable in structure, free of addiction and simple in synthesis process, is suitable for large-scale industrial production, and has the development prospect as cough relieving medicines.

Description

technical field [0001] The invention relates to naringenin derivatives, specifically naringenin derivatives substituted at positions 6 and 8 and their application in preparing medicines for improving respiratory system function, especially in cough medicines. Background technique [0002] Naringenin is the aglycone of naringin, which is widely found in the flower buds of cherry blossoms, plum blossoms, orange peel, orange red and other plant raw materials. Both naringenin and naringin have antitussive properties. The chemical properties of naringenin are stable. After entering the human body, it exists as a prototype drug; The disaccharide is hydrolyzed under water and becomes naringenin, so it mainly exerts pharmacological effects in the form of naringenin in the human body (Kazuo Ishii, Takashi Furuta, Yasuji Kasuya. Determination of naringin and naringenin in human plasma by high-performance liquid chromatography. Journal of Chromatography B, 683(1996); 225-229). The m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32A61K31/352A61P11/00A61P11/14
CPCA61K31/352C07D311/32A61K31/353A61P11/00A61P11/14
Inventor 苏薇薇王永刚吴忠
Owner SUN YAT SEN UNIV
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