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Pyrrolopyrimidine compounds with anti-tumor activity as well as application thereof

A compound and selected technology, applied in the field of medicine, can solve problems such as large body damage

Active Publication Date: 2019-08-02
HEBEI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above two drugs are cytotoxic drugs, which can cause great damage to the body, so it is particularly important to find alternative compounds

Method used

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  • Pyrrolopyrimidine compounds with anti-tumor activity as well as application thereof
  • Pyrrolopyrimidine compounds with anti-tumor activity as well as application thereof
  • Pyrrolopyrimidine compounds with anti-tumor activity as well as application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

[0050]

[0051] Add 2,6-diamino-4-oxopyrimidine (50g, 0.4mol) and sodium acetate (33.6g, 0.4mol) into water (150ml), heat to reflux, and add chloroacetaldehyde (60.9g, 0.47mol). After the reactant was refluxed for 18h, cooled to room temperature, the precipitate was filtered, washed with water (2×50mL) and acetone (2×50mL), and dried to obtain 2-amino-3,7-dihydro-4H-pyrrolo[2, 3-d] pyrimidin-4-one. ESI-MS(m / z):151.1[M+H] + .

Embodiment 2

[0052] Example 2 2-amino-6-iodo-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

[0053]

[0054] Dissolve 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (1.5g, 0.01mol) and iodine (5.1g, 0.02mol) in ethanol / Water (2:1, 100mL), heated to reflux for 2h. The precipitate was precipitated by cooling, the precipitate was filtered, washed with 1N sodium thiosulfate solution (2×30mL) and water (2×50mL) respectively, and dried to obtain 2-amino-6-iodo-3,7-dihydro-4H-pyrrole And[2,3-d]pyrimidin-4-one. ESI-MS(m / z):276.9[M+H] + .

Embodiment 3

[0055] Example 3 2-amino-6-(hydroxyethynyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

[0056]

[0057] At room temperature, 2-amino-6-iodo-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (2.7g, 0.01mol) and acetylene alcohol (0.43g, 0.01mol ) was dissolved in anhydrous DMF (30mL), palladium chloride (71mg, 0.40mmol), triphenylphosphine (131mg, 0.40mmol), triethylamine (10.1g, 0.1mol) and cuprous iodide (304mg , 1.60mmol), heated to 100°C for 12h. The solvent was evaporated under reduced pressure, and 2-amino-6-(hydroxyethynyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one was obtained by column chromatography. ESI-MS(m / z):191.1[M+H] + .

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Abstract

The invention relates to pyrrolopyrimidine compounds with anti-tumor activity, pharmacologically acceptable salt thereof and a pharmaceutical composition containing the pyrrolopyrimidine compounds. The invention also relates to an application of the compounds in the preparation of drugs for treating diseases related to DHFR (dihydrofolate reductase) and / or TS (thymidylate synthetase), in particular to preparation of anti-tumor drugs.

Description

technical field [0001] The invention relates to the field of medicine, in particular to pyrrolopyrimidine compounds with anti-tumor activity and uses thereof. Such compounds can effectively inhibit dihydrofolate reductase and / or thymidylate synthase. Background technique [0002] Tumor is a chronic disease that seriously endangers human health. With the development of society, the incidence of tumor is on the rise, and the cause of death from malignant tumors ranks first in the death list. Currently, tumor treatment mainly includes surgical therapy (operation), chemotherapy (chemotherapy), radiotherapy (radiotherapy), etc., among which drug therapy still plays an important role in cancer treatment. Therefore, finding anticancer drugs with high efficiency and low toxicity has always been an important goal of drug researchers. [0003] Folate plays an important role in cellular biosynthesis. The key enzymes in the folate cycle include dihydrofolate reductase (DHFR) and thymi...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P35/00A61P35/02A61P29/00A61P37/02A61P19/02A61P19/06A61P17/06A61P27/02A61P17/00A61P11/00A61P9/10A61P9/04A61P1/00A61P1/04A61P11/06A61P3/10A61P37/06A61P25/16A61P25/28A61P15/00A61P37/08A61P11/02A61P5/14
CPCC07D487/04A61P35/00A61P35/02A61P29/00A61P37/02A61P19/02A61P19/06A61P17/06A61P27/02A61P17/00A61P11/00A61P9/10A61P9/04A61P1/00A61P1/04A61P11/06A61P3/10A61P37/06A61P25/16A61P25/28A61P15/00A61P37/08A61P11/02A61P5/14
Inventor 王磊刘诣张丛颖高天丰郑倩倩
Owner HEBEI MEDICAL UNIVERSITY
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