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

A kind of thienopyrimidine compound and its preparation method and application

A compound and pyrimidine technology, applied in the field of thienopyrimidine compounds and their preparation, can solve problems such as physical hazards, toxic side effects, etc., and achieve the effect of preventing and treating cancer

Active Publication Date: 2019-09-20
SICHUAN UNIV
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, people often use surgery and chemotherapy to treat cancer, and these methods have caused serious harm to people's spirit and body.
At present, the antineoplastic drugs taken by cancer patients not only kill tumor cells, but also kill a large number of normal cells. toxic side effects

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 thienopyrimidine compound and its preparation method and application
  • A kind of thienopyrimidine compound and its preparation method and application
  • A kind of thienopyrimidine compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A thienopyrimidine compound: (2-((2S,6R)-2,6-dimethylmorpholinyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl) Preparation of Methanol: The synthetic route is as follows:

[0038]

[0039] 100 mmol of methyl 3-amino-2-thiophenecarboxylate and 500 mmol of urea were placed in a microwave reactor at 200°C for 30 min to obtain yellow crystalline compound Ib-1. 50 mmol of compound Ib-1 was added to 100 ml of phosphorus oxychloride mixed solution and refluxed at 110° C. for 10 hours to obtain the chlorinated product compound Ic-1. Suspend 34mmol of compound Ic-1 in 150ml of ethanol, add 100mmol of morpholine at a stirring speed of 100r / min, and react at room temperature for 2h to obtain compound Id-1. Mix 30mmol of compound Id-1, 90mmol of trifluoroacetic acid, and 45mmol of (2S,6R)-2,6-dimethylmorpholine in 100ml of n-butanol and reflux at 120°C for 3h to obtain compound Ie-1. Dissolve 20mmol of compound Ie-1 in 100ml of tetrahydrofuran, under nitrogen protection, add 24mm...

Embodiment 2

[0042] A kind of thienopyrimidine compound: the preparation of (4-morpholine-2-thiomorpholinothieno[3,2-d]pyrimidin-6-yl)methanol: the synthetic route is as follows:

[0043]

[0044] On the basis of Example 1, 10 mmol of compound Id-1, 30 mmol of trifluoroacetic acid, and 15 mmol of thiomorpholine were mixed in 30 ml of n-butanol and refluxed for 3 hours at 120 ° C to obtain compound Ie-2 . Dissolve 20mmol of compound Ie-2 in 100ml of tetrahydrofuran, under nitrogen protection, add 8mmol of Grignard reagent dropwise at -78°C, after the addition is complete, stir and react at a stirring speed of 50r / min for 2h, then add 15ml of DMF, and continue stirring for 4h Compound If-2 was obtained; at room temperature, 2 mmol of Compound If-2 was reduced with sodium borohydride in dichloromethane. After the reaction was completed, the reaction organic phase was washed three times with saturated brine, dried over anhydrous sodium sulfate, and subjected to silica gel column chromatogra...

Embodiment 3

[0047] A thienopyrimidine compound: the preparation of (2-(indol-1-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol: the synthetic route is as follows:

[0048]

[0049] On the basis of Example 1, 10 mmol of compound Id-1, 30 mmol of trifluoroacetic acid, and 15 mmol of indoline were mixed in 30 ml of n-butanol and refluxed at 130°C for 3.5 hours to obtain compound Ie- 3. Dissolve 20mmol of compound Ie-3 in 100ml of tetrahydrofuran, under nitrogen protection, add 8mmol of n-butyllithium dropwise at -78°C, after the addition is complete, stir and react at a stirring speed of 60r / min for 2h, then add 15ml of DMF, and continue stirring Compound If-3 was obtained after reaction for 4 hours; at room temperature, 2 mmol of compound If-3 was reduced with sodium borohydride in dichloromethane. After the reaction was completed, the reaction organic phase was washed with saturated brine three times, dried over anhydrous sodium sulfate, and silica gel column Compound 3 was isolat...

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 a thienopyrimidine compound, a preparation method and application thereof. The beneficial effects of the present invention are: the present invention provides the synthesis of thienopyrimidine compounds with brand-new structures and their application in anticancer. Because the PI3K‑Akt / mTOR signaling pathway plays an important role in the occurrence and development of tumors, and is closely related to the occurrence and development of tumors such as breast cancer, gastric cancer, colon cancer, rectal cancer, ovarian cancer, and prostate cancer, when the PI3K‑Akt / mTOR signaling pathway When the pathway is abnormal, it may cause cancer, and the thienopyrimidine compound of the present invention can inhibit the abnormality of the PI3K-Akt / mTOR signaling pathway, so as to achieve the purpose of preventing and treating cancer. The thienopyrimidine compounds described in the present invention provide new strategies and ideas for tumor treatment, and provide new directions and ideas for the research and development of antitumor drugs.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis and medical application, and specifically relates to a thienopyrimidine compound and its preparation method and application. Background technique [0002] Cancer is the first cause of death among Chinese residents, and with the development of economy and environmental pollution, the mortality rate of cancer is constantly rising, seriously endangering people's life and quality of life. At present, people often treat cancer by means of surgery and chemotherapy, which have caused serious harm to people's spirit and body. At present, the antineoplastic drugs taken by cancer patients not only kill tumor cells, but also kill a large number of normal cells. With toxic side effects. Such as: nausea, mouth ulcers, vomiting, diarrhea, hematuria, decreased immunity, susceptibility to infection, leukopenia, thrombocytopenia, etc., causing great harm to the human body. Therefore, finding ...

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): C07D495/04A61K31/5377A61K31/541A61P35/00
Inventor 陈元伟魏于全
Owner SICHUAN 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