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Icariin Derivatives

A technology of icariin and its derivatives, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., to achieve the effect of excellent drug effect

Inactive Publication Date: 2016-03-16
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 under ice-bath conditions, stir for 10 min, add 5.7 g (51.8 mmol, 7 equiv) of acetic anhydride dropwise, and Stir for 6 h, quench with ice water, filter, wash the solid with water, dissolve in ethyl acetate, dry over anhydrous MgSO4, concentrate in vacuo, and column chromatography 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 the reaction was monitored 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℃; 1HNMR (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,3H,J=6.24Hz...

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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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Patent Type & Authority Patents(China)
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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