Substituted phloroglucinol derivatives and application thereof

A technology of phloroglucinol and derivatives, which is applied in the field of series substituted phloroglucinol derivatives, and achieves the effects of stable physical and chemical properties, simple synthesis process, and improvement of respiratory system function.

Active Publication Date: 2013-03-27
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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  • Substituted phloroglucinol derivatives and application thereof
  • Substituted phloroglucinol derivatives and application thereof
  • Substituted phloroglucinol derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (E)-1-(2,4-Diallyloxy)-6-hydroxyphenyl)-3-(4-(allyl)phenyl)propene-1-one. (E)-1-(2,4-bis(allyloxy)-6-hydroxyphenyl)-3-(4-(allyloxy)phenyl) prop-2-en-1-one.

[0029]

[0030] Dissolve 5g of naringenin in 50ML of N,N-dimethylformamide (DMF), and then add 3eq of potassium carbonate K 2 CO 3 , the system was cooled to 0 degrees, and two equivalents of 2eq allyl bromide were added dropwise. After gradually rising to room temperature, react for 24 hours, add dropwise 600ML aqueous sodium chloride solution, and extract with ethyl acetate. The organic phase was washed three times with water, concentrated, and separated by silica gel column chromatography (petroleum ether: ethyl acetate = 20:1) to obtain 1.3 g of a light yellow solid. Melting point MP=55-58 degrees, thin layer chromatography: petroleum ether: ethyl acetate = 5:1, Rf=0.7, mass spectrum M+H= 393.3, yield = 18%.

[0031] NMR: 1 H-NMR(400Mhz,DMSO-d6): δ4.634(6H, dd, J1=17.6Hz; J2=4.8Hz, allyloxy-OCH2-),δ5.28...

Embodiment 2

[0035] 1-(2,4,6-Trihydroxy-3-propylphenyl)-3-4-hydroxyphenyl)propane 1-one.

[0036] 1-(2,4,6-trihydroxy-3-propylphenyl)-3-(4-hydroxyphenyl)propan-1-one.

[0037]

[0038] Dissolve 1 g of 6-allyl naringenin in 100 ml of ethanol. Add catalyst 10% Pd / C, 0.5g. Hydrogenation at normal pressure for 20 hours. The solid was removed by filtration, the filtrate was concentrated, and separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 2:1) to obtain 0.11 g of a light red solid. Melting point MP=183-185 degrees. Thin layer chromatography: petroleum ether: ethyl acetate = 1:1, Rf = 0.3, mass spectrum M-H = 315.3, HPLC purity = 99%.

[0039] NMR: 1 H-NMR(400Mhz, DMSO-d6): δ0.854 (3H,t,J=7.2Hz,H-3''), δ1.405(2H,q,J1=7.2Hz, H-2'') , δ2.386(2H,t, J=7.6Hz, H-1''), δ2.761(2H, t, J=8Hz,H-2), δ3.224(2H,t,J=7.6Hz , H-3), δ5.999(1H, s, H-6), δ6.663(2H, d, J=8.4Hz, H-3',H-5'), δ7.015(1H, d , J=8.4Hz, H-2',H-6'), δ9.110(-9OH), δ10.201(-4'OH), δ10.516...

Embodiment 3

[0043] (E)-1-(4-propenyloxy)-2,6-dihydroxyphenyl)-3-(4-(propenyloxy)phenyl)propen-1-one.

[0044] (E)-1-(4-(allyloxy)-2,6-dihydroxyphenyl)-3-(4-(allyloxy)phenyl)prop-2-en-1-one.

[0045]

[0046] Dissolve 5g of naringenin in 50ML of N,N-dimethylformamide (DMF), then add 3eq equivalent of potassium carbonate K2CO3, cool the system to 0 degrees, and dropwise add two equivalents of 2eq allyl bromide. After gradually rising to room temperature, react for 24 hours, add dropwise 600ML aqueous sodium chloride solution, and extract with ethyl acetate. The organic phase was washed three times with water, concentrated, and separated by silica gel column chromatography, petroleum ether: ethyl acetate = 10:1 to obtain 2 g of a light yellow mixture. Recrystallization from dichloromethane gave 0.6 g of a solid. Melting point MP=121-125 degrees, thin layer chromatography: Rf=0.7, petroleum ether: ethyl acetate = 2:1, Rf=0.7, mass spectrum M+H= 393.3.

[0047] NMR: 1 H-NMR(400Mhz, DMSO...

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Abstract

The invention discloses a series of substituted phloroglucinol derivatives with a structure shown as the general formula (I) in the specification, and a pharmaceutically acceptable salt thereof, wherein in the general formula (I), A is selected from H, methyl, ethyl or propyl; B1 is selected from H, allyl or natural glycosides disaccharides; B2 and B3 are respectively selected from H or allyl; and X-Y represents that two carbon atoms are connected by a single bond or a double bond. The invention further provides a preparation method of the compounds, and applications of the compounds to preparation of drugs for improving the function of respiratory systems, in particular cough-relieving drugs. Experiments prove that the derivatives, disclosed by the invention, have remarkable cough-relieving effect, no clinical addiction, stable physicochemical property and good prospect as clinical cough-relieving medicine, and are simple in synthetic process and suitable for large-scale production.

Description

technical field [0001] The present invention relates to a series of substituted phloroglucinol derivatives; and their application in the preparation of improving respiratory system function, especially cough medicine preparations. 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 to become 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 molecular structures of naringe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/64C07H15/203C07H1/00A61K31/12A61K31/7034A61P11/00A61P11/14
Inventor 王永刚苏薇薇彭维吴忠
Owner SUN YAT SEN UNIV
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