A kind of indole derivative and its use

A technology for indole derivatives and drugs, applied to indole derivatives and their application fields, can solve the problems of low oral bioavailability, low toxicity and side effects, respiratory and nervous system disorders, etc., and achieves small cytotoxicity, high selectivity index, Highly active effect

Active Publication Date: 2017-05-10
KUNMING UNIV OF SCI & TECH
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this type of drug has a certain curative effect, there are problems such as low oral bioavailability, toxic side effects such as nephrotoxicity, hepatotoxicity, bone marrow suppression, respiratory and nervous system disorders, etc., especially the emergence of drug-resistant virus strains, which urgently need research and development A new type of anti-HCMV inhibitor with high efficiency and low toxicity

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
  • A kind of indole derivative and its use
  • A kind of indole derivative and its use
  • A kind of indole derivative and its use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: Intermediate 2-((1 H -Indol-3-yl)-mercapto)- N -The synthesis of (2-bromophenyl) acetamide, concrete operation is as follows:

[0030]

[0031] Add 3-mercaptoindole (0.01mol) into a dry three-necked bottle, use 20ml N,N -After dissolving dimethylformamide (DMF), add anhydrous potassium carbonate solid (0.01mol), stir for a while, add 2-bromo- N -(2-Bromophenyl)acetamide (0.01mol), heated to 80°C and stirred for 5 hours, TLC tracked the reaction until the raw material point disappeared, stopped the reaction, poured the reaction solution into ice water and stirred to precipitate a precipitate, pumped filtered, washed with ice water, and dried to obtain 2-((1 H -Indol-3-yl)-mercapto)- N The crude -(2-bromophenyl)acetamide was directly used in the next step without purification.

Embodiment 2

[0032] Example 2: N -(3,4-Dimethoxyphenyl)-2-((1-(cyclohexylmethyl)-1 H - the synthesis of indol-3-yl) mercapto) acetamide (Ia), concrete operation is as follows:

[0033] Add 2-((1 H -Indol-3-yl)mercapto)- N -(3,4-dimethoxyphenyl)acetamide (2mmol), with 3mL N,N -After dimethylformamide (DMF) dissolves, add NaH (3mmol, 0.072g) three times under stirring condition in an ice bath, stir for a while, add bromomethylcyclohexane (3mmol, 0.5312g), stir for 3 Hour. The reaction was followed by TLC until the raw material point disappeared, and the reaction was stopped. The reaction solution was poured into ice water, extracted three times with ethyl acetate, and the ethyl acetate was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain the pure product of white powder solid Ia, and the detection results are as follows:

[0034]

[0035] Yield: 68.0%; Melting poi...

Embodiment 3

[0037] Example 3: N -(2-Bromophenyl)-2-((1-(cyclohexylmethyl)-1 H - the synthesis of indol-3-yl) mercapto) acetamide (Ib), concrete operation is as follows:

[0038]Add 2-((1 H -Indol-3-yl)mercapto)- N -(2-Bromophenyl)acetamide (2mmol), with 3mL N,N - After dimethylformamide (DMF) was dissolved, NaH (3mmol, 0.072g) was added three times under the condition of stirring in an ice bath, stirred for a while, bromomethylcyclohexane (3mmol, 0.5312g) was added, stirred for 5 Hour. The reaction was followed by TLC until the raw material point disappeared, and the reaction was stopped. The reaction solution was poured into ice water, extracted three times with ethyl acetate, and the ethyl acetate was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain pure white powder solid Ib. The test results are as follows:

[0039]

[0040] Ib

[0041] Yield: 73.5% Melti...

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 discloses an indole derivative shown in a general formula I, wherein R1 is selected from hydrogen, halogens (F, Cl, Br, I), methyl, ethyl and methoxyl; X is -CH2- or -C (= O) -; and R is cyclohexyl and phenyl. The compound disclosed by the invention has a novel structural skeleton, and has a good anti-HCMV-virus activity, therefore, the compound can be used as a lead compound for the preparation of anti-HCMV drugs.

Description

technical field [0001] The invention relates to an indole derivative and its application, and belongs to the technical field of organic compound synthesis and medical application. Background technique [0002] Human cytomegalovirus (HCMV) is a DNA virus ubiquitous in nature. The human infection rate is as high as 50%-80%. The initial infection can be transmitted through body fluid contact, blood transfusion or organ transplantation. It is an important conditional pathogenic factor, often causing mild or asymptomatic infection in immunocompetent healthy people, and in immunocompromised or deficient patients, after primary infection or latent infection of the virus, it can cause severe or even severe deadly disease. Primary or secondary HCMV infection in pregnant women can cause neonatal intrauterine infection or perinatal infection, which is currently the main cause of fetal birth defects; in organ transplantation, bone marrow transplantation, immunodeficiency patients and p...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/30A61P31/20
CPCC07D209/30
Inventor 王月平陆礼和朱媚平何海波常捷何严萍
Owner KUNMING UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap