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Icariin derivatives

A technology of icariin and derivatives is applied in the directions of sugar derivatives, sugar derivatives, sugar derivatives preparation, etc., to achieve the effect of excellent medicinal effect.

Inactive Publication Date: 2013-08-28
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] If new cholinesterase inhibitors can be found by improving the structure of icariin, it will bring good news to the treatment of Alzheimer's disease

Method used

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Examples

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Embodiment 1

[0035] Example 1 Preparation of Icariin Derivatives (Compounds 7, 8) of the present invention

[0036] Dissolve 5 g (7.4 mmol, 1 equiv) of ICA in 30 mL of DMF, add 5.7 g (51.8 mmol, 7 equiv) of triethylamine in an ice bath, stir for 10 min, add 5.7 g (51.8 mmol, 7 equiv) of acetic anhydride dropwise, and Stirred in the bath for 6h, quenched with ice water, filtered, washed with water, dissolved in ethyl acetate, dried over anhydrous MgSO4, concentrated in vacuo, and column chromatographed to obtain an alcoholic hydroxyl-protected icariin derivative (1 g, 15%). Dissolve 0.5 g (0.52 mmol, 1 equiv) of the protected product in 2 mL of anhydrous acetone, add appropriate amount of anhydrous K2CO3, catalytic amount of KI, stir for 10 min, add 0.55 mmol (1.1 equiv) of 1,3-dibromopropane or Ethyl bromoacetate, stirred at room temperature for 1-3h, and monitored the reaction by TLC. After the reaction was completed, the solid was removed by filtration, and the filtrate was concentrated ...

Embodiment 2

[0039] Example 2 Synthesis of Nitrogenous Derivatives of Icariin (Compounds 9 and 10)

[0040] Take 0.19g (0.17mmol, 1equiv) of compound 7 and dissolve it in anhydrous acetone, add an appropriate amount of K 2 CO 3 and catalytic amount KI, stirred at room temperature for 10 min, added piperidine or piperazine, stirred at room temperature for 30 min, filtered to remove solids, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography to obtain products 9 and 10.

[0041]Compound 9: Yellow powder, yield 90%.Mp.120~121℃; 1H NMR (400MHz, CDCl3) δ7.82(d, 2H, J=8.80Hz), 7.06(d, 2H, J=8.80Hz) ,6.92(s,1H),5.67(t,1H,J=2.08Hz),5.52(d,1H,J=7.04Hz),5.45(s,1H),5.32~5.40(m,2H),5.23~ 5.03(m, 2H), 5.06(t, 1H, J=6.56Hz), 4.96(t, 1H, J=10.08Hz), 4.64(bs, 1H), 4.39~4.31(m, 4H), 3.90(s ,3H),3.71~3.77(bs,4H),3.38~3.48(m,2H),2.50(d,2H,J=5.12Hz),2.13(s,3H),2.03(s,3H),2.00( d, 6H, J=3.84Hz), 1.68(s, 3H), 1.66(s, 3H), 1.63(s, 15H), 1.22~1.26(m, 3H), 0.81(d...

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Abstract

The invention provides icariin derivatives disclosed as Formula I. The icariin derivatives provided by the invention have in-vitro acetylcholine ester inhibiting activity, and have better drug effects than icariin, thereby providing a new option for clinical medicines for treating senile dementia.

Description

technical field [0001] The present invention relates to icariin derivatives. Background technique [0002] The most common form of dementia is Alzheimer's disease (AD), a progressive neurodegenerative disorder that is one of the most common causes of mental deterioration in middle-aged and older adults, with more than 250,000 people living with Alzheimer's disease. In the past few decades, a large amount of research work has been dedicated to exploring the pathogenesis of Alzheimer's disease and seeking drugs for the treatment of Alzheimer's disease, and various hypotheses have been put forward one after another, among which the latest and most mainstream hypothesis is the theory of beta-amyloid deposition (Aβ). However, there is no new drug based on this theory on the market. At present, three new phase III clinical drugs targeting Aβ have been declared a failure, which is a blow to the Aβ theory. At present, there are still many drugs under research based on this theory...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00A61K31/7048A61P25/28
CPCY02P20/55
Inventor 尹述凡李霞陈超董林李颖
Owner SICHUAN UNIV
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