6-bromotryptamine derivative as well as preparation method and application thereof

A technology of bromotryptamine and its derivatives, which is applied in the field of 6-bromotryptamine derivatives and its preparation, and can solve the problems of low activity and high toxicity

Active Publication Date: 2017-09-01
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A large number of active natural ingredients found in marine organisms, some can be directly used in the research and development of new drugs, but some active ingredients have problems such as low activity or high toxicity

Method used

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  • 6-bromotryptamine derivative as well as preparation method and application thereof
  • 6-bromotryptamine derivative as well as preparation method and application thereof
  • 6-bromotryptamine derivative as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0027] A 6-bromotryptamine derivative, the structural formula is represented by (I):

[0028] ..... (Ⅰ)

[0029] In the general formula (I), R is selected from -Cl or -H;

[0030] When R=-Cl, the compound is 6-bromotryptamine chlorophenylacetic acid;

[0031] When R=-H, the compound is 6-bromotryptamine phenylpropionic acid.

Embodiment 2

[0033] Preparation of Bromotryptamine Chlorophenylacetic Acid

[0034] Weigh 0.35mmol of chlorophenylacetic acid, dissolve it in 5mL of dichloromethane, then add 0.096g of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCL), and White turbid liquid, then add 0.068g 1-hydroxybenzotriazole (HOBT), stir at room temperature for 30min, the white turbidity disappears, check the reaction process with thin-layer chromatography, and when new spots appear, dissolve 7mL with 0.25 Mmol 6-bromotryptamine (where 6-bromotryptamine is 6-bromotryptamine hydrochloride obtained by removing hydrochloric acid with sodium hydroxide) was added dropwise to the above reaction solution in dichloromethane, stirred at room temperature overnight, and was analyzed by TLC After detection, it was found that the raw material point disappeared, the reaction was stopped, the solvent was distilled off, and the crude product was obtained, and a small amount of product was finally separated by semi...

Embodiment 3

[0037] Preparation of 6-bromotryptamine phenylpropionic acid

[0038] Weigh 0.35mmol of phenylpropionic acid, dissolve it in 5mL of dichloromethane, then add 0.096g of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCL), a white To the turbid liquid, add 0.068g 1-hydroxybenzotriazole (HOBT), stir at room temperature for 30min, the white turbidity disappears, detect the reaction process with thin-layer chromatography, and when new spots appear, dissolve 7mL with 0.25mmol 6-Bromotryptamine dichloromethane was added dropwise to the above reaction solution, stirred at room temperature overnight, detected by TLC, found that the raw material point disappeared, stopped the reaction, evaporated the solvent to obtain the crude product, and finally used semi-preparative liquid chromatography Trace product was isolated. Semi-preparative liquid chromatography conditions: dissolve the crude product in methanol, filter with a pore size of 0.22 μm, use an XBridge preparative...

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Abstract

The invention discloses a 6-bromotryptamine derivative as well as a preparation method and application thereof. The 6-bromotryptamine derivative is characterized by being expressed by a structural formula (I) and comprising 6-bromotryptamine chloro-phenylacetic acid and 6-bromotryptamine phenylpropionic acid. The preparation method comprises the following steps: weighing chloro-phenylacetic acid or phenylpropionic aci, dissolving with dichloromethane, further adding EDC.HCl till a white muddy liquid is generated, further adding HOBt, stirring for 30 minutes at normal temperature till a white muddy phenomenon is vanished, detecting the reaction process through thin-layer chromatography, when new points occur, dropping dichloromethane in which 6-bromotryptamine is dissolved into a reaction liquid, performing stirring reaction at room temperature, leaving to stand over night, performing thin-layer chromatography detection, terminating reaction if raw material points are eliminated, boiling off a solvent so as to obtain a crude product, finally separating a trace product by using semi-preparative type liquid chromatogram, and purifying, thereby obtaining the 6-bromotryptamine derivative. The 6-bromotryptamine derivative has the advantages that AchE can be remarkably inhibited, and the 6-bromotryptamine derivative has the potential of being developed into medicines for treating the Alzheimer's disease.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a 6-bromotryptamine derivative and its preparation method and application. Background technique [0002] Alzheimer's disease (AD), commonly known as senile dementia, is a neurodegenerative disease caused by impairment of language, learning, memory and other cognitive abilities of the central nervous system. It is one of the diseases with the highest incidence among the elderly. With the advent of an aging society, the number of AD cases is bound to increase sharply in the next few decades, which will put a huge pressure on my country's medical insurance system, and the demand for anti-senile dementia drugs will have a broad room for growth. At present, the more accepted pathological theory of AD in the world is "cholinergic deficiency theory", which believes that the loss of the neurotransmitter-acetylcholine (ACh) in the brain of Alzheimer's patients is the key caus...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/16A61P25/28
Inventor 黄春辉何山丁立建崔巍申屠杰益赵佳颖王敏君斯拉瓦·爱泼斯坦
Owner NINGBO UNIV
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