Thiophene and pyridine compound as well as preparation method and application thereof

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

Active Publication Date: 2016-08-03
SICHUAN UNIV
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  • 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

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  • Thiophene and pyridine compound as well as preparation method and application thereof
  • Thiophene and pyridine compound as well as preparation method and application thereof
  • Thiophene and pyridine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 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:

[0039]

[0040] 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

[0043] 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:

[0044]

[0045] 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

[0048] 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:

[0049]

[0050] 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 React for 4 hours to obtain compound If-3; 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 3 times with saturated brine, dried over anhydrous sodium sulfate, and silica gel column Compound 3 was isolated as a white so...

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PUM

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Abstract

The invention discloses a thiophene and pyridine compound as well as a preparation method and application thereof. The thiophene and pyridine compound as well as the preparation method and the application thereof have the benefits that the synthesis of the thiophene and pyridine compound with a novel structure and the application of the thiophene and pyridine compound to anti-cancer are provided; as a PI3K-Akt/mTOR signal path plays an important role in the occurrence and the development of tumors and has close occurrence and development relations with a breast cancer, a gastric cancer, a colon cancer, a rectal cancer, an ovarian cancer, a prostatic cancer and other tumors, when the PI3K-Akt/mTOR signal path is abnormal, the cancers may be caused; the thiophene and pyridine compound disclosed by the invention can restrain the abnormity of the PI3K-Akt/mTOR signal path, so as to achieve the purposes of preventing and treating the cancers. The thiophene and pyridine compound disclosed by the invention not only provides a new strategy and a new idea for tumor treatment, but also provides a new direction and a new idea for the research and development of anti-tumor drug.

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

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61K31/5377A61K31/541A61P35/00
Inventor 陈元伟魏于全
Owner SICHUAN UNIV
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