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Ceramide compound and application

A technology for ceramides and compounds, which is applied to ceramide compounds and application fields, can solve the problems of large molecular weight, difficult to large-scale preparation, limited practical clinical application, etc., and achieves the effect of improving cognition and high activity

Inactive Publication Date: 2017-05-10
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, NGF is a protein composed of more than 100 amino acids; due to reasons such as large molecular weight and strong polarity, it cannot pass through the blood-brain barrier, and it is difficult to prepare on a large scale, which limits its actual clinical application.
At present, no better treatment method has been found other than direct administration of drugs in brain surgery

Method used

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  • Ceramide compound and application
  • Ceramide compound and application
  • Ceramide compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Compound Ⅰ-1: (2S,3R,E)-2-Docosanoylaminooctadec-4-ene-1,3-diol;

[0036] Dissolve sphingosine (0.1mmol) in dry 8ml tetrahydrofuran, add dicyclohexylcarbodiimide (0.11mmol), 1-hydroxybenzotriazole (0.11mmol), docosanoic acid (0.11mmol ), react overnight at room temperature to obtain 42 mg of white solid, yield: 68%.

[0037] 1 H NMR (500MHz, CDCl 3 )δ6.23(dt, J=6.5,15.5Hz,1H),5.75(d,J=8.0Hz,1H),5.48(dd,J=6.5,15.5Hz,1H),4.31(t,1H), 3.93(dd,1H),3.90(m,1H),3.71(dd,1H),2.24(m,2H),2.05(m,2H),1.60(m,2H),1.25-1.31(m,58H) ,0.88(t,J=7.0Hz,6H); MS(m / z):622[M+H] + .

[0038] The structural formula of this compound is:

[0039]

Embodiment 2

[0041] Compound Ⅰ-2: (2S,3R,E)-2-Octadecanoylaminooctadec-4-ene-1,3-diol;

[0042] The synthetic method is the same as that of compound Ⅰ-1, and the reaction materials are: octadecanoic acid (0.11mmol), sphingosine (0.1mmol), 1-hydroxybenzotriazole (0.11mmol), dicyclohexylcarbodiimide ( 0.11 mmol), 41 mg of white solid was obtained, yield: 72%.

[0043] The structural formula of this compound is:

[0044]

Embodiment 3

[0046] Compound Ⅰ-3: (2S,3R,E)-2-Tetradecanoylaminooctadec-4-ene-1,3-diol;

[0047] The synthetic method is the same as that of compound Ⅰ-1, and the reaction materials are: myristic acid (0.11mmol), sphingosine (0.1mmol), 1-hydroxybenzotriazole (0.11mmol), dicyclohexylcarbodiimide ( 0.11 mmol), 36 mg of white solid was obtained, yield: 70%.

[0048] 1 H NMR (500MHz, CDCl 3 )δ6.24(dt, J=6.5,15.5Hz,1H),5.77(d,J=8.0Hz,1H),5.50(dd,J=6.5,15.5Hz,1H),4.33(t,1H), 3.92(dd,1H),3.91(m,1H),3.73(dd,1H),2.24(m,2H),2.08(m,2H),1.60(m,2H),1.26-1.37(m,42H) ,0.88(t,J=7.0Hz,6H); MS(m / z):510[M+H] + .

[0049] The structural formula of this compound is:

[0050]

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Abstract

The invention relates to a ceramide compound; in the structural general formula, m=2-12; n=0-20. The ceramide compound has significant pseudo neural growth factor activity, and is the small molecule compound capable of passing through blood-brain barrier. The structural general formula is shown as Figure.

Description

technical field [0001] The present invention relates to ceramide compounds, in particular to a ceramide compound and its application. Background technique [0002] With the acceleration of the aging process, the prevalence of senile dementia has increased significantly, and it has become the main cause of death in adults. Alzheimer's disease wipes out all memory, cognition, language and other abilities of the patient, and the patient has to go through a long and painful death process, causing huge mental and economic pressure on the patient and their relatives. [0003] Senile dementia can be roughly divided into three types: Alzheimer's disease (AD for short), vascular dementia (Vascular dementia, Vascular Dentia, VaD for short) and other types of dementia. So far, the exact pathological mechanism of AD is still unclear, and there is no program that can cure dementia or change the course of the disease. symptoms and delay the further development of dementia. Therefore, t...

Claims

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Application Information

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IPC IPC(8): C07C233/18A61K31/164A61P25/28A61P25/00A23L33/10
CPCA23V2002/00C07C233/18A23V2200/322
Inventor 戚建华边凌林罗燕長田裕之向兰曹雪丽
Owner ZHEJIANG UNIV
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