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Homodimer for caffeic acid and ferulic acid, and preparation method and pharmaceutical composition thereof

A kind of drug and doublet technology, applied in the field of homodimer, can solve the problems that are not enough to delay the development of Alzheimer's disease and can't effectively treat neurodegenerative diseases

Active Publication Date: 2015-04-29
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in recent years, the development of drugs targeting Aβ has failed one after another, because only clearing amyloid-β or acting on a single target, such as acetylcholinease inhibitors, is not enough to delay the development of Alzheimer's disease
With the development of related disciplines such as systems biology and network pharmacology, the new point of view believes that the single-molecule single-target strategy of "recovering the body by inhibiting a molecular target in the pathogenesis of the disease through drugs" cannot be effectively treated. Neurodegenerative diseases, cancer, depression and other diseases

Method used

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  • Homodimer for caffeic acid and ferulic acid, and preparation method and pharmaceutical composition thereof
  • Homodimer for caffeic acid and ferulic acid, and preparation method and pharmaceutical composition thereof
  • Homodimer for caffeic acid and ferulic acid, and preparation method and pharmaceutical composition thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] (E)-3-(3,4-dihydroxyphenyl)-N-{4-[3-(3,4-dihydroxyphenyl)-acrylamide]-phenyl}-acrylamide

[0031] Reagents: caffeic acid (166mg, 0.92mmol), p-phenylenediamine (50mg, 0.46mmol), BOP (407mg, 0.92mmol), treated according to the synthesis method of the general reaction formula to obtain a yellow solid with a yield of 21.4%.

[0032] 1 H-NMR (400MHz, DMSO-d 6 )d10.05(s, 2H), 8.32(s, 1H), 7.63(s, 4H), 7.38(d, J=15.5Hz, 2H), 7.01(s, 2H), 6.90(d, J=7.9 Hz, 2H), 6.78 (d, J = 8.1 Hz, 2H), 6.54 (d, J = 15.4 Hz, 2H).

[0033] 13 C NMR (100MHz, DMSO-d 6 )d 163.89, 148.68, 147.98, 140.51, 134.99, 126.37, 122.03, 119.66, 119.00, 115.82, 110.97.

Embodiment 2

[0035]

[0036] (E)-3-(4-Hydroxy-3-methoxyphenyl)-N-{4-[3-(4-hydroxy-3-methoxyphenyl)acrylamido]phenyl}-propene Amide

[0037] Reagents: ferulic acid (178mg, 0.92mmol), p-phenylenediamine (50mg, 0.46mmol), BOP (407mg, 0.92mmol), treated according to the general reaction formula to obtain a yellow solid with a yield of 30.2%.

[0038] 1 H NMR (400MHz, DMSO-d 6 )d10.06(s, 2H), 9.51(s, 2H), 7.65(s, 3H), 7.48(d, J=15.5Hz, 2H), 7.18(s, 2H), 7.11-7.00(m, 2H ), 6.83 (d, J=8.1 Hz, 2H), 6.64 (d, J=15.6 Hz, 2H), 3.83 (s, 6H).

[0039] 13 C NMR (100MHz, DMSO-d 6 )d 163.89, 148.68, 147.98, 140.51, 134.99, 126.37, 122.03, 119.66, 119.00, 115.82, 110.97, 55.66.

Embodiment 3

[0041]

[0042] (E)-3-(3,4-dihydroxyphenyl)-N-(4-{[3-(3,4-dihydroxyphenyl)-acrylamide]-methyl}-benzyl)-propene Amide

[0043] Reagents: caffeic acid (133.2mg, 0.74mmol), p-benzylidene diamine (50mg, 0.37mmol), BOP (325mg, 0.74mmol), processed according to the synthesis method of the general reaction formula to obtain a yellow solid with a yield of 25.6%.

[0044] 1 H NMR (400MHz, DMSO-d 6 )d8.45(s, 2H), 7.27(d, J=15.8Hz, 2H), 7.24(s, 4H), 6.94(s, 2H), 6.84(d, J=7.5Hz, 2H), 6.74( d, J = 8.0 Hz, 2H), 6.38 (d, J = 15.6 Hz, 2H), 4.35 (d, J = 4.6 Hz, 4H).

[0045] 13 C NMR (100MHz, DMSO-d 6 )d165.50, 147.40, 145.58, 139.54, 138.17, 127.45, 126.41, 120.51, 118.35, 115.82, 113.92, 42.09

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Abstract

The invention relates to homodimers for synthesizing a series of caffeic acids and ferulic acids. Structural formulas of the homodimers are as shown in a formula (I). The inhibiting effects and the free radical scavenging capacities of the homodimers on beta-starch amyloid protein self-aggregation can adjusted through an exchange joint, so that the homodimers can simultaneously act on a plurality of targets, and can be prepared into appropriate drug dosage forms for treating parkinson's disease, and diseases related to the beta-starch amyloid protein and oxidative stress.

Description

field of invention [0001] The present invention relates to the synthesis of a series of homodimers of caffeic acid and ferulic acid. The structural formula is shown in formula (I). By changing the linker, it adjusts its inhibitory effect on the self-aggregation of β-amyloid protein and its ability to scavenge free radicals, so that it can act on multiple targets at the same time. They can be formulated into appropriate pharmaceutical dosage forms for the treatment of Alzheimer's disease, and diseases related to beta-amyloid and oxidative stress. Background of the invention [0002] Alzheimer's disease (Alzheimer's disease, AD) is a neurodegenerative disease characterized by progressive cognitive dysfunction and memory impairment. Cellular function is gradually lost, resulting in impairment of memory, judgment, sense of orientation, attention, and language, accompanied by changes in behavior and personality, and eventually death of the patient within 5-10 years. Its three ...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C235/38C07C235/34A61K31/167A61K31/165A61P25/28
Inventor 皮荣标何细新杨晓红姜伊鸣陈紫薇陈美惠王胜男文石军刘培庆
Owner SUN YAT SEN UNIV
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