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Scutellarein carbamate derivates, preparation method and application thereof

A technology of scutellarin aglycone and carbamate, applied in the field of scutellarin aglycone 4'-position carbamate derivatives and scutellarin aglycone derivatives, can solve the problem of poor solubility of scutellarin, Short half-life in vivo, serious side effects, etc.

Inactive Publication Date: 2009-01-07
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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  • Scutellarein carbamate derivates, preparation method and application thereof
  • Scutellarein carbamate derivates, preparation method and application thereof
  • Scutellarein carbamate derivates, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of 6,7-(diphenylmethylenedioxy)-5,4'-dihydroxyflavone (3)

[0031] Add 13.3 g (0.047 mol) of scutellarin aglycon and 16.7 g (0.070 mol) of diphenylmethylene chloride into the reaction flask in sequence, mix well, raise the temperature to 170°C for 1 hour under the protection of inert gas, and cool to room temperature Afterwards, add an appropriate amount of chloroform, suction filter while hot, evaporate the filtrate to remove the solvent under reduced pressure, and recrystallize the residue with chloroform to obtain 13.83 g of light brown needle crystals, mp: 250-252°C, yield 65.9%. 1 H NMR (DMSO-d 6 , 400MHz) δ: 13.18 (brs, 1H, 5-OH), 10.41 (brs, 1H, 4'-OH), 7.95 (d, J=8.8Hz, 2H, Ar'-H 3，5 ), 7.61(s, 1H, Ar-H 8 ), 7.59~7.56(m, 4H, Ph-H), 7.51~7.47(m, 6H, Ph-H), 6.94(d, J=8.8Hz, 2H, Ar’-H 2，6 ), 6.88(s, 1H, Ar-H 3 ); HR-TOFMS m / z: 449.1036 ([C 28 h 18 o 6 -H] + Calculated value: 449.1025).

Embodiment 2

[0033] Preparation of 6,7-(diphenylmethylenedioxy)-5-hydroxy-4'-(N-tetrahydropyrrolecarboxy)-flavone (5a)

[0034] Add 1.0g (2.21mmol) of intermediate 3, 0.35mmol of tetrahydropyrrolecarbonyl chloride, 30ml of N,N-dimethylformamide and 5ml of anhydrous pyridine into the reaction flask, stir and react at room temperature for 15 hours (the reaction process is followed by TLC ); after the reaction, add an appropriate amount of ice water, filter with suction, and wash the filter cake with a small amount of ice water, and the resulting crude product is purified by column chromatography (eluent: chloroform-ethyl acetate) to obtain 0.593 g of a light yellow powder solid, mp: 226~228°C, yield 49.0%. 1 H NMR (CDCl 3 , 400MHz) δ: 7.86 (d, J=8.8Hz, 2H, Ar'-H 3，5 ), 7.64~7.61(m, 4H, Ph-H), 7.41~7.37(m, 6H, Ph-H), 7.31(d, J=8.8Hz, 2H, Ar’-H 2，6 ), 6.65(s, 1H, Ar-H 8 ), 6.62(s, 1H, Ar-H 3 ), 3.56(t, J=6.8Hz, 2H, NCH 2 -H α ), 3.53(t, J=6.8Hz, 2H, NCH 2 -H β ), 1.92(t, J=6.8Hz, 2H, ...

Embodiment 3

[0036] Preparation of 6,7-(diphenylmethylenedioxy)-5-hydroxy-4'-(N,N-dimethylcarbamoyloxy)-flavone (5b)

[0037] The operation process is the same as in Example 2, except that tetrahydropyrrolecarbonyl chloride is replaced by N, N-dimethylcarbamoyl chloride to obtain 6,7-(diphenylmethylenedioxy)-5-hydroxyl-4'- (N,N-Dimethylcarbamoyloxy)-flavone is light yellow powder solid, mp: 230-232°C, yield 71.2%. 1 H NMR (CDCl 3 , 400MHz) δ: 7.86 (d, J=8.8Hz, 2H, Ar'-H 3，5 ), 7.64~7.61(m, 4H, Ph-H), 7.41~7.37(m, 6H, Ph-H), 7.28(d, J=8.8Hz, 2H, Ar’-H 2，6 ), 6.65(s, 1H, Ar-H 8 ), 6.62(s, 1H, Ar-H 3 ), 3.13 (s, 3H, CH 3 ), 3.04 (s, 3H, CH 3 ).

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Abstract

The invention relates to a novel scutellarin aglycon 4 (1)-position carbamate derivant (1), a preparation method and the application thereof. A pharmacological experiment proves that the compounds have obvious inhibitory activity of acetylcholinesterase and have protective effect with different degrees on PC12 cell trauma induced by H2O2, so the compounds can be used for preparing the drugs for treating neurodegenerative diseases such as vascular dementia, AD (presenile dementia), etc.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new type of scutellarin aglycone derivatives, in particular to scutellarin aglycone 4'-position carbamate derivatives, a preparation method thereof and a method for preparing and treating vascular dementia, albino Application in drugs for neurodegenerative diseases such as 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 emotion and personality. It is a chronic progressive disease. In China, Japan and other Asian countries, vascular dementia ...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61K31/496A61K31/5377A61K31/4025A61P25/28
Inventor 邓勇沈怡吴贝钟裕国
Owner SICHUAN UNIV
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