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3,3'-disubstituted bipyridine derivatives, and preparation method and application thereof

A bipyridine and derivative technology, which is applied in the field of 3,3'-disubstituted bipyridine derivatives and their preparation, can solve the problems of neuron loss of cognitive function, decline, insufficient explanation for the accumulation of peptides, etc. The method is simple, the raw material is cheap, and the effect of low cytotoxicity

Active Publication Date: 2018-08-21
GUANGDONG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Deposition of excess Aβ can lead to a series of inflammatory responses, leading to neuronal loss and cognitive decline
However, the self-aggregating properties of Aβ are not sufficient to explain the accumulation of peptides in specific brain regions in AD patients

Method used

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  • 3,3'-disubstituted bipyridine derivatives, and preparation method and application thereof
  • 3,3'-disubstituted bipyridine derivatives, and preparation method and application thereof
  • 3,3'-disubstituted bipyridine derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of N,N'-[(2,2'-bipyridyl)-3,3'-diyl]bis(4-chlorobenzamide)(compound 3a)

[0030] Add 0.20g of 4-chlorobenzoic acid and 0.14mL of N,N-diisopropylethylamine (DIEA) into a round-bottomed flask containing 8mL of DMF, stir to dissolve the solid completely, and cool to 0-5°C with an ice bath . After adding 0.21 g of 2-(7-benzotriazole oxide)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), stir for 5 minutes, then add 3,3'-di Amino-2,2'-bipyridine 0.10g, stirred in ice bath for 10min, then naturally warmed to room temperature, followed by TLC, after the reaction was completed, the reaction solution was poured into 20mL of ice water, stirred, and a light yellow solid precipitated. The solid was suction filtered, washed with water and dried. The crude product was purified by silica gel chromatography to obtain 3a as a light yellow powder with a yield of 81%. 1 H NMR (400MHz, CDCl 3 ): δ14.35(s,2H),9.39(s,2H),8.42(s,2H),7.65(d,J=8.0Hz,4H),7.47(d,J=8.0Hz,4H)...

Embodiment 2

[0032] Embodiment 2: the synthesis of compound 3b

[0033] The method was the same as in Example 1, except that benzoic acid was used instead of 4-chlorobenzoic acid, and the crude product was purified by silica gel column chromatography to obtain light yellow solid 3b with a yield of 84%. 1 H NMR (400MHz, CDCl 3)δ14.56(s, 2H), 9.43(d, J=7.9Hz, 2H), 8.42(s, 2H), 8.08(d, J=5.7Hz, 4H), 7.57(d, J=7.0Hz, 6H),7.48-7.45(m,2H)..ESI-MS m / z:395.5[M+H] + .

[0034]

Embodiment 3

[0035] Embodiment 3: the synthesis of compound 3c

[0036] The method was the same as in Example 1, except that 3,4-dimethoxybenzoic acid was used instead of 4-chlorobenzoic acid, and the crude product was purified by silica gel chromatography to obtain 3c as a white solid with a yield of 85%. 1 H NMR (400MHz, CDCl 3 ):δ14.35(s,2H),9.39(s,2H),8.42(s,2H),7.64(s,4H),7.45(s,2H),7.02(s,2H),3.99(s, 12H).ESI-MS m / z:515.5[M+H] + .

[0037]

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PUM

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Abstract

The invention discloses 3,3'-disubstituted bipyridine derivatives and a preparation method thereof, and an application of the 3,3'-disubstituted bipyridine derivatives in preparation of drugs againstAlzheimer's disease. The 3,3'-disubstituted bipyridine derivatives have chemical formulas as shown in a formula I and a formula II which are described in the specification. In the formula I and the formula II, R is selected from the group consisting of -H, halogen, -O(CH2)mCH3, and an amino group substituted by one or more methyl or ethyl groups; R1 is selected from the group consisting of -O(CH2)mCH3 and -OH; and R2 is selected from the group consisting of C1-C4 aliphatic hydrocarbons, an amino group substituted by one or more methyl or ethyl groups, and two groups which are described in thespecification. The invention also discloses the preparation method and the application for the derivatives provided by the invention. The 3,3'-disubstituted bipyridine derivatives provided by the invention have the ability of inhibiting Abeta aggregation and metal complexing, can inhibit metal ion induced Abeta aggregation activity, and have low biological toxicity and good safety. Thus, the 3,3'-disubstituted bipyridine derivatives provided by the invention have broad application space in preparation of drugs against Alzheimer's disease.

Description

technical field [0001] The invention relates to the technical fields of medicine and chemical industry, and more specifically, to a 3,3'-disubstituted bipyridyl derivative and its preparation method and application. Background technique [0002] Alzheimer's disease (AD), also known as senile dementia, is a chronic, progressive degenerative disease of the central nervous system. In recent years, with the development of society and the improvement of people's living standards, the world's population is aging, so the incidence of AD is increasing year by year, and it has become one of the main diseases that seriously threaten the health and quality of life of the elderly. So far, the pathogenesis of AD has not been clarified, and it may involve various factors such as gene defects, metabolic disorders, free radical damage, immune neuroinflammation, neuronal apoptosis, and environmental toxins. Aiming at these factors, many hypotheses have been put forward, among which the amyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/75A61K31/444A61K31/496A61P25/28A61P21/04
CPCA61P21/04A61P25/28C07D213/75
Inventor 王晓琴赵楚萍何明华钟志乾陈嘉和王燕纯王茂钦
Owner GUANGDONG MEDICAL UNIV
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