Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Isatin derivative 6-bromo-2,3-dioxoindolin-N-halogen substituted phenylacetamide, and preparation method and application thereof

A technology of dioxoindoline and phenylacetamide, applied in the application of antiepileptic drugs, in the field of preparation of antidepressants, which can solve problems such as depression, aggravation of depression, and reduction of folic acid levels, and achieve rapid onset and short reaction time Flexible, low neurotoxic effects

Inactive Publication Date: 2015-12-02
ZHEJIANG OCEAN UNIV
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In clinical application, a variety of drugs have been used alone for antidepressant patients, such as amitepine, clomipramine, moclobemide, fluoxetine, paroxetine, sertraline, citalopram, etc.; There are also many kinds of antiepileptic drugs that can be used alone in clinical application, such as phenytoin, phenobarbital, valproic acid, carbamazepine, lamotrigine, etc.; but doctors will not choose it for patients with epilepsy and depression. Antidepressant drugs, as a result, can make the patient's depression worse. Some drugs, including epilepsy drugs, can also cause depression. Some antiepileptic drugs are closely related to behavior changes and depression. Other antiepileptic drugs can reduce the level of folic acid in the body. can also lead to depression

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Isatin derivative 6-bromo-2,3-dioxoindolin-N-halogen substituted phenylacetamide, and preparation method and application thereof
  • Isatin derivative 6-bromo-2,3-dioxoindolin-N-halogen substituted phenylacetamide, and preparation method and application thereof
  • Isatin derivative 6-bromo-2,3-dioxoindolin-N-halogen substituted phenylacetamide, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 16

[0023] Embodiment 16-Bromo-2,3-dioxoindoline-N-halogen substituted phenylacetamide derivative physical constant

[0024]

[0025]

[0026] (a) Preparation of 6-bromo-dioxoindoline-1-yl-N-(2-fluorophenyl)acetamide

[0027] Add 30mL DMF to a 50mL round-bottomed flask, add 3.4mmol compound II (6-bromo-2,3-indoledione) 0.5g in batches under ice-cooling, stir and dissolve, then add 3.4mmol K 2 CO 3 0.3g, stirred at room temperature for 1h. Add 0.42 g of 3.4 mmol of 2-fluorophenyl chloroacetamide and 0.5 g of potassium iodide 6 mmol, raise the temperature to 80° C. for 8 h, and monitor the reaction by TLC until the reaction is complete. Cool to room temperature, add distilled water about 6 times the volume of the reaction solution, add dropwise dilute hydrochloric acid to adjust the pH value of the solution to 3-4, stir for 10 min, filter with suction, dry, and recrystallize the crude product with ethanol to obtain product a. The spectral data of the compound are as follows...

Embodiment 2

[0038] Embodiment 2 anticonvulsant pharmacological experiment and neurotoxicity experiment

[0039] The forced swimming test is the most commonly used experiment for the study of depressants and antidepressants. The sum of the time for mice to give up swimming and struggling in the water is called the immobility time, which reflects the symptoms of helplessness in mice, while the forced swimming test The prolongation of the immobility time in the middle showed depression-like symptoms. The compound provided by the invention is screened by the mouse forced swimming test to evaluate its antidepressant efficacy and safety.

[0040] (1) Mice forced swimming test:

[0041] a method: see (PorsoltRDetal, ArchIntPharmaeodynTher, 1997) and other reported methods, after intraperitoneal injection for 30 minutes, put the mouse into the XSC-mouse constant temperature swimming instrument (in a bucket with a water depth of 10cm and a diameter of 34cm, the water temperature is 25 ± 2°C), ob...

Embodiment 3

[0051] Convulsion experiment induced by embodiment 3 pentylenetetrazole

[0052] The invention provides a basis for studying the therapeutic effect of the isatin derivative 6-bromo-2,3-dioxoindoline-N-halogen substituted phenylacetamide on a mouse convulsion model induced by pentylenetetrazole.

[0053] a Model establishment: The convulsion mouse model was injected intraperitoneally with 90 mg / kg pentylenetetrazole, and the occurrence of convulsions in mice was observed within 30 minutes after intraperitoneal injection of pentylenetetrazole. Convulsions were diagnosed according to the Racine standard, and the acute convulsion model was successfully established if the mice had seizures of grade 4 or above.

[0054] b Observation indicators: observe the number of mice with convulsions in each group, calculate the percentage of convulsions, compare the difference between the administration group and the control group, and determine whether there is anticonvulsant activity. Index...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a novel anti-depression and anti-convulsion compound and a medicinal salt thereof. The compound is an isatin derivative 6-bromo-2,3-dioxoindolin-N-halogen substituted phenylacetamide represented by formula (I) shown in the specification. A preparation method of the isatin derivative 6-bromo-2,3-dioxoindolin-N-halogen substituted phenylacetamide has the characteristics of flexible reaction time, high yield, simple operation and wide application range, and is suitable for industrial production. The compound has very low neurotoxicity, a pharmacological experiment result of mouse forced swimming using the synthesized new compound shows that the new compound has similar anti-depression activity with a contrast medicine fluoxetine and has very low neurotoxicity (TD50 is greater than 1000mg / kg) and very high safety, and an anti-convulsion experiment result shows that the isatin derivative 6-bromo-2,3-dioxoindolin-N-halogen substituted phenylacetamide can resist convulsion induced by a chemical substance pentylenetetrazole, so the isatin derivative 6-bromo-2,3-dioxoindolin-N-halogen substituted phenylacetamide is a very good anti-depression and anti-epilepsy compound.

Description

technical field [0001] The invention relates to a class of medicinal compounds and a preparation method thereof, in particular to a isatin derivative 6-bromo-2,3-dioxoindoline-N-halogen substituted phenylethyl ether used as antidepressant and antiepileptic Amide, preparation method and application in preparation of antidepressant and antiepileptic drugs. Background technique [0002] Depression is a psychosomatic disease characterized by abnormal behavior and low mood as the main symptoms. Depression can affect people's digestion, immunity, nervous system and other functions, and even cause damage, and the disease has the characteristics of high morbidity, refractory cure and high recurrence rate. Epilepsy is a collective term used to describe a group of chronic convulsive disorders that are characterized by transient seizures accompanied by loss or disturbance of consciousness. Relevant studies have shown that epilepsy and anxiety and depression may have a common neurobio...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D209/38A61P25/24A61P25/08
CPCC07D209/38
Inventor 关丽萍甄兴华曲有乐杨立业
Owner ZHEJIANG OCEAN UNIV
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com