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Scutellarin carbamate derivative, preparation method and use thereof

A technology of carbamates and scutellarin aglycone is applied in the directions of drug combinations, pharmaceutical formulations, and medical preparations containing active ingredients, which can solve the problems of serious toxic and side effects, poor solubility of scutellarin, and short half-life in vivo.

Inactive Publication Date: 2012-07-25
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Because scutellarin has problems such as poor solubility, low bioavailability, short half-life in vivo, and serious side effects, it will be of great significance to use scutellarin as a lead substance for structural modification in order to find therapeutic drugs with better pharmacological activity and curative effect

Method used

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  • Scutellarin carbamate derivative, preparation method and use thereof
  • Scutellarin carbamate derivative, preparation method and use thereof
  • Scutellarin carbamate derivative, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 5,6,7-trimethoxy-4'-( N - Preparation of tetrahydropyrrolecarboxy)-flavone (T-1)

[0035] Add 5,6,7-trihydroxy-4'-( N -Tetrahydropyrrole carboxyloxy)-flavone 1.0 mmol, acetone 30 ml, anhydrous potassium carbonate 12.0 mmol and dimethyl sulfate 10.0 mmol, heated and refluxed and stirred for 24 hours (the reaction process was tracked by TLC); after the reaction, Filtrate while hot, wash the filter cake with a small amount of acetone, evaporate the filtrate to remove the solvent under reduced pressure, add 30 ml of ice water to the residue, and filter with suction. The obtained crude product is recrystallized from ethanol to obtain 0.39 g of a yellow powder solid, with a yield of 92.0%; HR- TOFMS (+Q) m / z :426.1551 ([C23 h 23 NO 7 +H] + Calculated value: 426.1553).

Embodiment 2

[0037] 5-hydroxy-6,7-dimethoxy-4'-( N -tetrahydropyrrolecarboxy)-flavone (T-2) and 5,7-dihydroxy-6-methoxy-4′-( N - Preparation of tetrahydropyrrolecarboxy)-flavone (T-3)

[0038] Add 5,6,7-trihydroxy-4'-( N -Tetrahydropyrrolecarboxy)-flavone 1.0 mmol, acetone 30 ml, anhydrous potassium carbonate 3.0 mmol and dimethyl sulfate 2.9 mmol, heat up to 40-45°C and keep stirring for 18 hours (track the reaction process with TLC) After the reaction, filter while it is hot, wash the filter cake with a small amount of acetone, evaporate the filtrate to remove the solvent under reduced pressure, add 30 ml of ice water to the residue, and filter with suction. The obtained crude product is dried and purified by column chromatography (eluent: chloroform- Methanol=50:1 v / v), to get 5-hydroxy-6,7-dimethoxy-4′-( N -tetrahydropyrroloyloxy)-flavone yellow powder solid 0.186 g, yield 45.2%; HR-TOFMS (+Q) m / z :412.1399 ([C 22 h 21 NO 7 +H] + Calculated: 412.1396); and 5,7-dihydroxy-6-m...

Embodiment 3

[0040] 5,6,7-trimethoxy-4'-( N,N - Preparation of dimethylcarbamoyloxy)-flavone (T-4)

[0041] The operating process is the same as in Example 1, except that 5,6,7-trihydroxyl-4'-( N -Tetrahydropyrrolecarboxy)-flavone with 5,6,7-trihydroxy-4'-( N,N -Dimethylcarbamoyloxy)-flavone instead, dimethyl sulfate is replaced by iodomethane to give 5,6,7-trimethoxy-4'-( N,N -Dimethylcarbamoyloxy)-flavone yellow powder solid, yield 90.0%; HR-TOFMS (+Q) m / z :400.1395 ([C 21 h 21 NO 7 +H] + Calculated value: 400.1396).

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Abstract

The invention discloses a 4'-carbamate derivative of scutellarin shown in formula (I), a preparation method of the compound and application of the compound in preparing medicines for preventing and / or treating various symptoms and diseases caused by acetyl cholinesterase and / or mediated by free radicals, such as vascular dementia and Alzheimer's disease. In the formula, each of R1, R2 and R3 independently represents H, C1-C12 alkyl or R6CO, wherein R6 represents C1-C12 alkyl, but R1, R2 and R3 are not H at the same time; each of R4 and R5 independently represents H, C1-C12 alkyl, C1-C6 fatty alcohol, or an ester formed by the C1-C6 fatty alcohol and C1-C6 carboxylic acid, the C1-C6 carboxylic acid, or an ester formed by the C1-C6 carboxylic acid and the C1-C6 fatty alcohol; or R4NR5 represents a morpholine ring, a piperidine ring, a 4-benzyl piperidine ring, a piperazine ring, the piperazine ring with the 4-position substituted by C1-C12 alkyl, or a tetrahydropyrrole ring.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new type of scutellarin derivatives, in particular to carbamate derivatives at the 4'-position of scutellarin, a preparation method thereof and a preparation method for preventing or / and treating various causes. Acetylcholinesterase or / and free radicals mediate the use of symptoms or diseases caused by drugs, including but not limited to neurodegenerative diseases such as vascular dementia and Alzheimer's disease (Alzheimer's disease). Background technique [0002] Vascular dementia (Vascular Dementia, VD) is caused by various types of cerebrovascular diseases (including ischemic cerebrovascular disease, hemorrhagic cerebrovascular disease, acute and chronic hypoxic cerebrovascular disease, etc.) It is a clinical syndrome of cognitive dysfunction, and its main clinical manifestations include: decline in cognitive ability, memory, and social life ability, as well as changes in e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61K31/4025A61K31/352A61K31/5377A61K31/453A61K31/496A61P25/28
Inventor 邓勇杜俊蓉桑志培王宇强晓明
Owner SICHUAN UNIV
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