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Alkanosulfide-terminated oligomer-PEG modified amino-pyrazolo[3,4-d] pyrimidine derivative and application to non-small cell lung cancer resistance

A technology of alkyl and compound, applied in the field of pyrazolo[3,4-d]pyrimidine derivatives, which can solve the problems of high toxicity and side effects, low bioavailability, and low specificity

Active Publication Date: 2017-11-24
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are a variety of drugs for the treatment of cancer on the market, they all have various defects, such as low bioavailability, low specificity, and large toxic and side effects.
These defects are often caused by the structural characteristics of the compound itself and its target, and it is difficult to overcome it in further research and development.

Method used

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  • Alkanosulfide-terminated oligomer-PEG modified amino-pyrazolo[3,4-d] pyrimidine derivative and application to non-small cell lung cancer resistance
  • Alkanosulfide-terminated oligomer-PEG modified amino-pyrazolo[3,4-d] pyrimidine derivative and application to non-small cell lung cancer resistance
  • Alkanosulfide-terminated oligomer-PEG modified amino-pyrazolo[3,4-d] pyrimidine derivative and application to non-small cell lung cancer resistance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The preparation of embodiment 1 compound 4

[0045]

[0046] Compound 1 (269mg, 1mmol) was dissolved in 1,4-dioxane / water (4:1) 150ml solution, and transferred to a 250ml round bottom flask, and then added (1.38g, 10mol) to the reaction solution Potassium carbonate, after stirring at room temperature for three minutes, add catalyst bis-diphenylphosphinoferrocene palladium chloride (73.1 mg, 0.1 mol), heat the reaction mixture to 100 ° C, detect the reaction by TLC, after the reaction is completed , first, after the reaction solution is cooled, add 50ml of distilled water, then transfer to a separatory funnel, add 100ml of dichloromethane to extract 3 times, combine the organic phases, add anhydrous sodium sulfate, spin dry the organic solvent, and dichloromethane / methanol (100:2.5) as eluent, separated and purified by silica gel column chromatography to obtain intermediate compound 2 (200 mg, 70%).

[0047] 1 H NMR (600MHz, DMSO-6d) δ9.83(s, 1H, HOAr), 8.28(s, 1H,...

Embodiment 2

[0054]

[0055] Synthesis of compound 2:

[0056] Compound 1 (269mg, 1mmol) was dissolved in 1,4-dioxane / water (4:1) 150ml solution, and transferred to a 250ml round bottom flask, and then added (1.38g, 10mol) to the reaction solution Potassium carbonate, after stirring at room temperature for three minutes, add catalyst bis-diphenylphosphinoferrocene palladium chloride (73.1 mg, 0.1 mol), heat the reaction mixture to 100 ° C, detect the reaction by TLC, after the reaction is completed , first, after the reaction solution is cooled, add 50ml of distilled water, then transfer to a separatory funnel, add 100ml of dichloromethane to extract 3 times, combine the organic phases, add anhydrous sodium sulfate, spin dry the organic solvent, and dichloromethane / methanol (100:2.5) as eluent, separated and purified by silica gel column chromatography to obtain intermediate compound 2 (200 mg, 70%).

[0057] 1 H NMR (600MHz, DMSO-6d) δ9.83(s, 1H, HO Ar), 8.28(s, 1H, CH), 6.97-7.83(m...

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PUM

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Abstract

The invention relates to an alkanosulfide-terminated oligomer-PEG modified amino-pyrazolo[3,4-d] pyrimidine derivative and application to non-small cell lung cancer resistance. The invention discloses a pyrazolo[3,4-d] pyrimidine derivative shown as a formula (I). The compound provided by the invention has the obvious growth inhibition effect on tumor cells, can be used for preventing and / or treating tumor related diseases, and has wide application prospects. The formula I is shown in the specification.

Description

technical field [0001] The invention belongs to the field of compound drugs, in particular to pyrazolo[3,4-d]pyrimidine derivatives and applications thereof. Background technique [0002] Malignant tumors grow fast and show invasive growth, prone to hemorrhage, necrosis, ulcers, etc., and often have distant metastasis, resulting in body weight loss, weakness, anemia, loss of appetite, fever, and severe damage to organ functions, eventually causing The death of the patient poses a huge threat to the health and life of the crowd. [0003] Surgical treatment Radical resection is still the most basic and commonly used cancer treatment method at present, but usually the resection operation is relatively traumatic, and it will cause damage to body tissues and loss of blood after surgery, so it is not suitable for the elderly and those with poor physical fitness. Poor patients and patients with heart, lung, liver and other important organ diseases are selected, so it is necessary ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61P35/00
CPCC07D487/04
Inventor 陈勃江何杨李为民周兴龙柴莹莹李长富沈珍马蓓蓓黄日东陈海
Owner WEST CHINA HOSPITAL SICHUAN UNIV