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

Thiobenzoyl derivative and application thereof

A technology of thiobenzoyl derivatives and alkylthio groups, applied in the field of chemistry, can solve problems such as unreported compounds, and achieve novel structure and excellent effect of inhibiting the activity of cancer cells

Active Publication Date: 2021-06-01
SHENYANG RES INST OF CHEM IND
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But, the compound similar to structure of the present invention has not been reported

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
  • Thiobenzoyl derivative and application thereof
  • Thiobenzoyl derivative and application thereof
  • Thiobenzoyl derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0257] Embodiment 1: the synthesis of compound 6-121

[0258]

[0259] Add 2-aminothiobenzamide (J.Heterocyclic Chem., 43,1281 (2006)) 3.3g, 2,4,5 trichloropyrimidine 3.6g, sodium carbonate 2.2g, DMF50mL in 100mL flask, Stir and heat at 80°C for 4 hours. After the reaction is detected by TLC, add 150 mL of water, extract with 50 mL of ethyl acetate × 3, combine the organic phases, dry over anhydrous sodium sulfate, and perform column chromatography (eluent is ethyl acetate and petroleum ether ( Boiling range 60-90 ℃), volume ratio is 1:2) purification to obtain 0.53g compound 6-121, 2-((2,5-dichloropyrimidin-4-yl)amino)-N-methylthiobenzene Formamide, yellow solid.

Embodiment 2

[0260] Embodiment 2: the synthesis of compound 7-120

[0261]

[0262] Add 0.53 g of 2-((2,5-dichloropyrimidin-4-yl) amino)-N-methylthiobenzamide, 0.3 g of 4-morpholinoaniline, and p-toluenesulfonate monohydrate into a 100 mL flask 0.3g of acid, 30mL of n-butanol, stirred and heated at 100°C for 4 hours, after the reaction was detected by TLC, add 150mL of water, extract with 50mL of ethyl acetate × 3, combine the organic phases, dry over anhydrous sodium sulfate, column chromatography (elution The solvent is ethyl acetate and petroleum ether (boiling range 60-90° C., volume ratio 2:1) to obtain 0.11 g of compound 7-120 as a gray solid.

[0263] The characterization data of some compounds prepared according to the above preparation method are as follows:

[0264] Compound 7-120:

[0265] 1 H NMR (600MHz, DMSO- d6 )δ10.61(d, J=4.0Hz, 1H), 9.62(s, 1H), 9.16(s, 1H), 8.22(d, J=7.4Hz, 1H), 8.13(s, 1H), 7.48- 7.44(m, 3H), 7.30(d, J=7.5Hz, 1H), 7.19(t, J=7.5Hz, 1H), 6.83(d, J...

Embodiment 3

[0269] Embodiment 3: In vitro detection experiment (MTT method) to cancer cell inhibitory effect is as follows

[0270] Human cancer cell lines used: human ovarian adenocarcinoma cell SK-OV-3, human cervical cancer cell Hela, human non-small cell lung cancer cell A549, and human anaplastic large cell KARPAS299.

[0271] Using in vitro cell culture technology, the inhibitory rate of 5 concentrations of test samples on the growth of human cancer cells was determined by conventional MTT method.

[0272] The cells were taken out from the incubator, washed twice with PBS, digested with 0.25% trypsin solution, added medium to stop the digestion, centrifuged and blown with a pipette to form a cell suspension, and counted under an inverted microscope. Prepare cells into a cell suspension with a concentration of 5x104 / mL, add 100 μL of cells to each well of a 96-well plate, place in 5% carbon dioxide, and culture overnight at 37°C in humidified air, and add the above-mentioned drugs to...

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 belongs to the field of chemistry, and particularly relates to a thiobenzoyl derivative and an application of the thiobenzoyl derivative in treating cancers, inflammations or immune system diseases. The structure of the thiobenzoyl derivative is shown as a general formula I; the definition of each substituent group in the formula is shown in the specification. The compound of the invention is useful in the treatment of cancer diseases.

Description

technical field [0001] The invention belongs to the field of chemistry, and specifically relates to a thiobenzoyl derivative and the application of the derivative in the treatment of cancer, inflammation or immune system diseases. Background technique [0002] Patent WO2018019252 discloses the general formula of pyrimidine compounds shown in the following general formula and the specific compound 11 as the effect of cancer treatment. [0003] [0004] However, compounds similar in structure to the present invention have not been reported. Contents of the invention [0005] The purpose of the present invention is to provide a thiobenzoyl derivative and the application of the derivative in treating cancer. [0006] In order to achieve the above object, the technical solution adopted by the present invention is: [0007] A thiobenzoyl derivative, which is a compound represented by general formula I and a pharmaceutically acceptable salt thereof: [0008] [0009] in ...

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 Applications(China)
IPC IPC(8): C07D239/47A61P35/00A61P29/00A61P37/06A61P35/02
CPCC07D239/47A61P35/00A61P29/00A61P37/06A61P35/02Y02P20/55
Inventor 冉兆晋柴宝山王云华毕弋王婉秋焦佳媛吴依蒙赵宪成石凯强
Owner SHENYANG RES INST OF CHEM IND
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