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

Oxindole compound as well as preparation method and application thereof

A technology of oxindole and compounds, applied in organic chemistry, drug combination, antineoplastic drugs, etc., to achieve the effects of strong compatibility, economical reaction steps, and wide application prospects

Inactive Publication Date: 2022-03-01
JIANGXI NORMAL UNIV
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese invention patent CN108047119A discloses a 3-fluoroalkenyloxindole-3-trifluoromethyloxindole compound, which has an excellent effect of inhibiting the growth of breast cancer cells and can be used in drugs for the treatment of breast cancer diseases , to provide the possibility for the clinical treatment of breast cancer, but the compound only has oxindole, which has the problem of only anticancer activity, which limits its application

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
  • Oxindole compound as well as preparation method and application thereof
  • Oxindole compound as well as preparation method and application thereof
  • Oxindole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] An oxidindole compound, having the structural formula shown in A1:

[0042]

[0043] The preparation method of above-mentioned oxindole compounds is as follows:

[0044] Add 0.2 mmol N-(2-iodophenyl)-N-methylmethacrylamide, 0.26 mmol 1-(6-methylpyridin-2-yl)-3-phenylacetylene to the reaction tube Propyl ester, 0.01 mmol tetrakis(triphenylphosphine) palladium, 0.4 mmol potassium carbonate, 2 ml N,N-dimethylformamide, reacted at 80°C under nitrogen protection for 6 hours, stopped the reaction and cooled to room temperature, added With 5 milliliters of water, the reaction solution was extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain a crude product, which was subjected to column chromatography (eluent had a volume ratio of 7: 1 mixed solvent of petroleum ether and ethyl acetate) separation and purification to obtain the target produc...

Embodiment 2

[0047] A kind of oxindole compound, its structural formula is consistent with embodiment 1.

[0048] The difference between the preparation method of the oxindole compound and Example 1 is that toluene is used as the organic solvent in this example, and the yield is 59%.

Embodiment 3

[0050] An oxidindole compound whose structural formula is consistent with that of Example 1.

[0051] The difference between the preparation method of the oxindole compound and Example 1 is that acetonitrile is used as the organic solvent in this example, and the yield is 42%.

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 oxoindole compound and a preparation method and application thereof, the structural formula of the oxoindole compound is shown in the specification, in the structural formula, R1 and R3 are independently selected from hydrogen, C1-C5 alkyl or halogen; r2 is selected from alkyl or benzyl of C1 to C5; r4 is selected from acyl; and R5 is selected from phenyl, substituted phenyl or C1-C5 alkyl. The oxoindole compound contains indolizine and oxoindole at the same time, can have the biological activity of indolizine and oxoindole, and has wide application prospects. According to the preparation method, the methacrylamide compound and the propargyl pyridine compound which are low in price and easy to obtain are used as raw materials, the polysubstituted oxoindole compound is synthesized in one step, and the preparation method has the advantages that additional ligands are not needed, the reaction steps are economical, the substrate universality is good, the functional group compatibility is high, and the preparation method can be used for amplifying to gram-level reaction.

Description

technical field [0001] The present invention relates to the technical fields of chemical synthesis and medicine, and more specifically relates to an oxindole compound and its preparation method and application. Background technique [0002] Oxindole is a heterocyclic skeleton structure that widely exists in natural products and drug molecules. Many compounds containing oxindole structure have good biological activity and important pharmaceutical value. For example, natural Uncaria alkaloids with oxindolin as the core have antihypertensive, vasodilation, antidepressant, antiepileptic and antitumor activities (J. Ethnopharmacol, 2010, 130:127-133; Food. Chem. Toxicol, 2007, 45:2206-2218). Sunitinib, a drug molecule containing oxindolinone, is effective in the treatment of gastrointestinal stromal tumors and metastatic renal cell carcinoma (J MedChem, 2003, 46: 1116-1119). Chinese invention patent CN108047119A discloses a 3-fluoroalkenyloxindole-3-trifluoromethyloxindole comp...

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): C07D471/04A61P35/00A61P31/04A61P31/02
CPCC07D471/04A61P35/00A61P31/04A61P31/02
Inventor 刘建超肖霄
Owner JIANGXI NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com