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N-substituted sophora flavescens olefine acid derivative as well as preparation method and application thereof

A technology of matrine and compounds, applied in the field of medicine for diseases, can solve the problem of Coxsackie virus with no specific medicine

Inactive Publication Date: 2012-09-12
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no specific drug against Coxsackie virus, and clinically it is mainly symptomatic treatment

Method used

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  • N-substituted sophora flavescens olefine acid derivative as well as preparation method and application thereof
  • N-substituted sophora flavescens olefine acid derivative as well as preparation method and application thereof
  • N-substituted sophora flavescens olefine acid derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0060] Step 2. Preparation of diphenyldiazomethane:

[0061] Take 9.8g (0.05mol) of benzophenone hydrazone, add 120mL of petroleum ether (30-60℃), add 13.05g (0.15mol) of electrolytic manganese dioxide, reflux for 1h, filter with suction, wash the filter cake with petroleum ether, and combine the filtrates , used directly in the next reaction.

[0062] Step 3. Preparation of diphenylmethyl ester of α and β matrine:

[0063] Add the petroleum ether solution of diphenyldiazomethane directly to the methanol solution of SC-1, stir at room temperature until the purple color completely subsides, about 12 hours, concentrate to dryness, add dichloromethane and water layer, dichloromethane layer with anhydrous Na 2 SO 4 After drying, a dichloromethane solution of diphenylmethyl esters of α and β matrine acids was obtained, which was directly used in the subsequent synthesis reaction of N-substituted α and β matrine acids.

[0064] Step 4. Preparation of diphenylmethyl esters of N-s...

Embodiment 1

[0072] The synthesis of embodiment 1.N-benzenesulfonyl matrine acid (SC-16A) and (SC-16B):

[0073]

[0074] Add K 2 CO 3 3.45g (0.025mol), 1.60mL (12.5mmol) of benzenesulfonyl chloride was added dropwise, stirred at room temperature, until TLC detection, the raw material point disappeared, filtered off inorganic salts, concentrated, flash column chromatography, 3g white solid was obtained, added m-formazine 15 mL of phenol was reacted at 80-90°C for 8 hours, 50 mL of methyl ethyl ketone was added, extracted with water three times, the aqueous layers were combined and concentrated to obtain 1.6 g of a white solid. Flash column chromatography yielded 0.6 g of SC-16A and 0.8 g of SC-16B.

[0075] SC-16A:

[0076] HRMS-ESI (M / Z): C 21 h 29 N 2 o 4 S 405.1833(M+1); 406.1909(M+2); 407.1851(M+3);

[0077] 1 H-NMR (CD 3 OD, δppm): 7.73-7.75 (2H, m), 7.50-7.59 (3H, m), 5.42-5.45 (2H, m), 3.79 (1H, dd, J=4.4, 12.4Hz), 3.49-3.54 ( 1H, m), 3.09(1H, t, J=12.4Hz), 2.98(2H, t...

Embodiment 2

[0081]The synthesis of embodiment 2.N-p-toluenesulfonyl matrine acid (SC-18A) and (SC-18B):

[0082]

[0083] Add K 2 CO 3 3.45g (0.025mol), 2.38g (12.5mmol) of p-toluenesulfonyl chloride was added dropwise, stirred at room temperature, until the TLC detection, the raw material point disappeared, filtered off inorganic salts, concentrated, flash column chromatography, to obtain 3.5g white solid, added 15 mL of m-cresol was reacted at 80-90°C for 8 hours, 50 mL of methyl ethyl ketone was added, extracted with water for 3 times, the aqueous layers were combined and concentrated to obtain 1.8 g of white solid. Flash column chromatography yielded 0.7 g of SC-18A and 0.8 g of SC-18B.

[0084] SC-18A:

[0085] HRMS-ESI (M / Z): C 22 h 31 N 2 o 4 S 419.2006(M+1); 420.2083(M+2); 421.2011(M+3);

[0086] 1 H-NMR (CD 3 OD, δppm): 7.62 (2H, d, J = 8Hz), 7.34 (2H, d, J = 8Hz), 5.38-5.49 (2H, m), 3.74 (1H, dd, J = 4.4, 12Hz), 3.43 (1H, t, J=9.6Hz), 2.91-3.05(5H, m), 2.76(1H, s)...

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Abstract

The invention relates to an N-substituted sophora flavescens olefine acid derivative represented by a general formula IA or IB, a preparation method thereof, a medicine composite containing the derivative, a method for utilizing the derivative to treat diseases caused by Coxsackie B viruses, and an application of the derivative to prepare a medicine for treating the diseases caused by the Coxsackie B viruses.

Description

technical field [0001] The present application relates to an N-substituted matrinenic acid derivative, a preparation method thereof, a pharmaceutical composition containing the derivative, a method for using the derivative to treat diseases caused by Coxsackie B virus, and the derivative Use of the compound in the preparation of medicines for treating diseases caused by Coxsackie B virus. Background technique [0002] Coxsackie virus is a group of viruses isolated from the feces of children clinically diagnosed with polio in Coxsackie, New York, USA in 1948. It belongs to the Enterovirus genus of the Picornaviridae family. The pathogen Coxsackieviruses are divided into two categories according to their biological characteristics: Type A and Type B. Eckovirus and poliovirus, which belong to the enterovirus class, are now called "parvoviruses". Coxsackie A virus infection is more common in children than in adults. The main features of clinical manifestations are acute feve...

Claims

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Application Information

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IPC IPC(8): C07D471/16A61K31/4375A61P31/14A61P9/00
CPCY02P20/55
Inventor 蒋建东宋丹青高丽梅李玉环高荣梅王辉强杜娜娜
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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