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A kind of triazolopyrimidine compound and its preparation method and application

An azolopyrimidine and compound technology, which is applied in the field of triazolopyrimidine compounds and their preparation, and achieves the effects of good mTOR inhibitory activity, good drug prospect and good anticancer effect

Active Publication Date: 2021-07-13
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it has been reported that advanced HCC is less sensitive to ionizing radiation (IR), and the whole liver can only be safely irradiated with IR doses of 90 Gy, respectively, and these safe doses are only a fraction of those required for cancer control.

Method used

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

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Embodiment 1

[0075]

[0076] Methyl 3-((7-(3-methoxyphenyl)-5-methyl-6-((4-methylpyridin-3-yl)carbamoyl)-4,7-dihydro-[1 ,2,4]Synthesis of triazol[1,5-a]pyrimidin-2-yl)thio)propionate (2a)

[0077] Step 1: Preparation of methyl 3-((5-amino-1H-1,2,4-triazol-3-yl)thio)propionate (intermediate 1)

[0078] Methyl 3-bromopropionate (14.36g, 0.086mol) was dissolved in 40ml of absolute ethanol for later use. In a 500ml reaction vessel, NaOH (3.44g, 0.086mol) was dissolved in 200ml of purified water and stirred until completely dissolved. 3-Amino-5-thio-1,2,4-triazole (10.00 g, 0.086 mol) was then added and stirred. After 30 minutes, a mixture of methyl 3-bromopropionate and ethanol was added. React overnight at room temperature. After the reaction was complete, it was extracted with ethyl acetate, washed with saturated sodium chloride and washed with Na 2 SO 4 dry. Methyl 3-((5-amino-1H-1,2,4-triazol-3-yl)thio)propanoic acid (11.65 g, yield 67%) was obtained.

[0079] Step 2: Preparatio...

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Abstract

The invention discloses a triazolopyrimidine compound and its preparation method and application. The triazolopyrimidine compound is a kind of mTOR inhibitor with novel structure. The new compound skeleton is found by the method, and the targeted design is carried out according to the different structures of PI3K and mTOR proteins, so it has the characteristics of high activity and high selectivity. Moreover, the invention creatively uses it as a radiosensitizer in the treatment of cancer, which can increase the sensitivity of cancer cells to radiotherapy, greatly reduce the radiation dose in radiotherapy, reduce side effects, and improve the effect of radiotherapy.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a triazolopyrimidine compound and its preparation method and application. Background technique [0002] Rapamycin (mTOR) is a serine / threonine protein kinase with a molecular weight of about 280kda. It plays an important role in a variety of signaling pathways and affects a variety of physiological functions, such as growth, proliferation, protein synthesis, autophagy, metabolism, and survival. Excessive activation of mTOR is one of the important reasons leading to excessive proliferation and malignant transformation of cells, while inhibiting mTOR activity can achieve anti-tumor, anti-inflammatory, immunosuppressive and anti-aging effects. [0003] Advanced liver cancer (Hepatocellular carcinoma) is a very terrible disease. Due to the resistance of liver cancer cells to cellular chemotherapy and individual differences in patients' sensitivity to molecular...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/519A61P35/00A61P37/06A61P31/04A61P31/12A61P9/14A61P39/06A61P25/28A61P29/00A61P35/02A61P43/00A61K41/00
CPCA61K41/0038A61P9/14A61P25/28A61P29/00A61P31/04A61P31/12A61P35/00A61P35/02A61P37/06A61P39/06A61P43/00C07D487/04
Inventor 曹爽张珩陈永收冯瑛琪任一鑫陈思奥
Owner WUHAN INSTITUTE OF TECHNOLOGY
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