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Application of α-carbolin derivatives in the preparation of anti-myocardial hypoxia-reoxygenation injury drugs

A technology of myocardial hypoxia and derivatives, which is applied in drug combinations, pharmaceutical formulations, and cardiovascular system diseases. problem, to achieve a good protection effect

Active Publication Date: 2020-06-23
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs still have defects such as weak specificity, low curative effect, and obvious long-term tolerance.
This hinders the effective treatment of myocardial ischemia-reperfusion injury

Method used

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  • Application of α-carbolin derivatives in the preparation of anti-myocardial hypoxia-reoxygenation injury drugs
  • Application of α-carbolin derivatives in the preparation of anti-myocardial hypoxia-reoxygenation injury drugs
  • Application of α-carbolin derivatives in the preparation of anti-myocardial hypoxia-reoxygenation injury drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1 compound 1---the preparation of 2-methyl 3-bromo-alpha carbolin

[0044] Step 1: Preparation of 1-(5-bromo-6-methyl-2-pyridyl)-1H-benzotriazole

[0045] At 120°C, 2,5-dibromo-6-picoline (3.0g, 11.96mmol) and benzotriazole (2.85g, 23.91mmol) were mixed and dissolved in DMSO (100mL), and K 2 CO 3(11.26g, 81.47mmol), reacted under stirring and reflux for 48h, left to cool, added 300mL water to dissolve, extracted with EtOAc, then backwashed with water, concentrated under reduced pressure, the residue was purified by silica gel column chromatography to obtain the product, the yield 39.2%.

[0046] Step 2: Preparation of 2-methyl 3-bromo-αcarbolin

[0047] At 160°C, take polyphosphoric acid (80mL) in a reaction flask, add 1-(5-bromo-6-methyl-2-pyridyl)-1H-benzotriazole (2.03g, 7.0mmol ) in polyphosphoric acid, stirred for 4 hours, added 150mL of water to dissolve, and used Na 2 CO 3 Adjust pH=9, filter, and extract the filtrate with EtOAc, anhydrous Na 2 ...

Embodiment 2

[0048] Embodiment 2 compound 2---the preparation of 2-methyl 3-amido-alpha carbolin

[0049] Step 1: Preparation of 1-(5-cyano-6-methyl-2-pyridyl)-1H-benzotriazole

[0050] At 120°C, take 2-methyl 3-bromo-αcarbolin (compound 1, 1.0g, 3.46mmol), potassium ferrocyanide (382.19mg, 1.04mmol), bis(triphenylphosphine) di Palladium chloride (121.38mg, 172.93mmol), sodium carbonate (1.1g, 10.38mmol) and palladium acetate (77.65mg, 345.86mmol) in a reaction flask, and measure N,N-dimethylacetamide (18ml) Placed in a reaction flask, under the protection of nitrogen, the reaction was stirred for 4-8h. After completion of the reaction, add 100mL of water to dissolve, filter, and extract the filtrate with EtOAc, anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, the residue was purified by silica gel column chromatography to obtain 1-(5-cyano-6-methyl-2-pyridyl)-1H-benzotriazole with a yield of 94%.

[0051] Step 2: Preparation of 2-methyl 3-amido-αcarbolin

[...

Embodiment 3

[0053] Embodiment 3 compound 3---the preparation of 2-methyl 3-glutamic acid diester base-alpha carbolin

[0054] Step 1: Preparation of 2-methyl 3-carboxy-αcarbolin

[0055] At 120°C, take 2-methyl 3-amido-αcarbolin (compound 2, 1.0g, 4.42mmol) in a reaction flask, add 20ml of concentrated hydrochloric acid, stir the reaction for 24h, and use K 2 CO 3 Adjust pH=9, filter, and extract the filtrate with EtOAc, anhydrous Na 2 SO 4 Dry, concentrate under reduced pressure, and purify the residue by silica gel column chromatography to obtain 2-methyl 3-carboxy-αcarbolin with a yield of 97.2%.

[0056] Step 2: Preparation of 2-methyl-3-glutamate dimethyl-alpha carboline

[0057] Take 2-methyl 3-carboxy-αcarbolin (500.00mg, 2.21mmol), dimethyl glutamate (464.61mg, 2.65mmol), Carter condensing agent (1.47g, 3.32mmol), triethanolamine (5ml ) in a reaction flask, stirred at room temperature for 20 h. Add 120mL water to dissolve, filter, and extract the filtrate with EtOAc, anhydro...

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Abstract

The invention relates to the technical field of medicines, in particular to application of an alpha-carboline derivative in preparation of an anoxia-reoxygenation injury drug against a myocardial ischemia-reperfusion injury. The compound is stable in solution, has an obvious protective activity against a myocardial anoxia-reoxygenation injury, especially an anoxia-reoxygenation injury of a myocardial ischemia-reperfusion injury, and can protect myocardium from an anoxia-reoxygenation injury at 100 mu mol / L, and thus a new option is provided for protection of the anoxia-reoxygenation injury against a myocardial ischemia-reperfusion injury and the myocardial anoxia-reoxygenation injury.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to the application of an α-carbolin derivative in the preparation of a drug against myocardial hypoxia-reoxygenation injury. Background technique [0002] Coronary heart disease refers to heart disease caused by myocardial ischemia and hypoxia caused by coronary artery sclerosis, and is one of the main causes of human death. The World Health Organization (WHO) statistical report shows that about 3.8 million men and 3.4 million women die of coronary heart disease every year. The main feature of coronary heart disease is myocardial hypoxia-reoxygenation injury. It can be seen that myocardial hypoxia-reoxygenation injury has become one of the main hazards of ischemic heart disease to human health. [0003] Drugs for the treatment of myocardial ischemia-reperfusion injury are well known in existing studies. Among the various known therapeutic drugs, the more effective drugs are...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/437A61P9/10
CPCC07D471/04
Inventor 周孟何迅廖祥明廖尚高王珊杨馨张金娟陈腾祥李芮张荣红徐国波李靖李勇军王永林
Owner GUIZHOU MEDICAL UNIV
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