Method for preparing acanthus alkaloid A with anti inflammatory and analgesic activities and derivatives thereof

An anti-inflammatory, analgesic, and rat-like technology, applied in the directions of organic active ingredients, medical preparations containing active ingredients, anti-inflammatory agents, etc., can solve the problems of high price of carbonyl diimidazole, environmental pollution, etc. cost effect

Inactive Publication Date: 2009-04-01
GUANGXI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But in this patent, 4-hydroxybenzoxazol-2-one is only used as an intermediate of dye synthesis, and no research on pharmacological activity

Method used

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  • Method for preparing acanthus alkaloid A with anti inflammatory and analgesic activities and derivatives thereof
  • Method for preparing acanthus alkaloid A with anti inflammatory and analgesic activities and derivatives thereof
  • Method for preparing acanthus alkaloid A with anti inflammatory and analgesic activities and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The method for preparing bougainvillea alkaloid A:

[0029] Mix 16.16g (0.10mol) of 2-aminoresorcinol hydrochloride and 30.04g (0.60mol) of urea and put it into a 250mL three-necked flask. For about 1h, continue to heat up to 150°C for about 1h. Finally, heat up to 190°C until no NH3 escapes, which lasts for about 6h. Heating was stopped, cooled to obtain a solid, and the solid was washed several times with cold water to obtain a crude product. Heat the crude product in n-butanol to reflux, filter to remove insoluble matter, concentrate the filtrate to dryness, add 80% ethanol to dissolve the obtained solid, reflux, cool slightly, add an appropriate amount of activated carbon, boil for several minutes, filter while hot, and concentrate to an appropriate amount. Cool to precipitate crystals, filter with suction, and dry at 80°C to 100°C to constant weight to obtain white bougainvillea alkaloid A. Yield 60%. mp: 293°C to 294°C.

Embodiment 2

[0031] The method for preparing 4-butyryloxybenzoxazol-2-one:

[0032] Add 4.53g (0.03mol) of bougainvillea alkaloid A and 7.58g (0.075mol) of triethylamine into the three-necked flask, dissolve it in acetone, and dilute with acetone under stirring in an ice bath at 5°C to 10°C. 4.79g (0.045mol) of butyryl chloride, after about 30 minutes of dripping, reacted in an ice-water bath at 0°C to 5°C for 2h, transferred to a water bath at 40°C to 45°C for 3h, raised the temperature to reflux, and tracked and detected the raw material point by TLC Disappeared, stopped the reaction, cooled to room temperature. Neutralize to neutral with 0.1mol / L HCl, filter, recover acetone to obtain a light yellow oil, stand at room temperature, precipitate a white needle-like solid, filter, wash the solid with distilled water, and recrystallize with 80% ethanol to obtain a white Acicular 4-butyryloxybenzoxazol-2-one. Yield 60%. mp: 115°C to 117°C.

Embodiment 3

[0034] The method for preparing 3-methyl-4-methoxybenzoxazol-2-one:

[0035]Add 3.02 g (0.02 mol) of bougainvillea alkaloid A into the three-necked flask, add acetone to dissolve, then add 9.20 mL (0.04 mol) of 15% NaOH solution dropwise in an ice bath at 5°C to 10°C while stirring. After a large amount of white precipitate appeared, it was transferred to a water bath at 40°C, and methyl iodide diluted with acetone was added dropwise under stirring, kept for 3 hours, and then heated to reflux. The disappearance of the raw material point was detected by TLC tracking, and the reaction was stopped and cooled to room temperature. Neutralize to neutral with 0.1mol / L HCl, filter, recover acetone to obtain a solid, and wash with distilled water. The solid was dissolved in 50ml of chloroform, and the insoluble matter was removed. The filtrate was collected and evaporated to dryness in chloroform to obtain a crude product. Dissolve the crude product in an appropriate amount of 80% eth...

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Abstract

The invention relates to a preparation method of an acanthus ilicifolius L.alkaloid A with the anti-inflammatory and analgesic activity and the corresponding derivative thereof. The chemical name of the acanthus ilicifolius L.alkaloid A is 4-hydroxylbenzoxazole-2-ketone which can be prepared through heating 2-aminoresorcinol hydrochloride and carbamide without solvent; the synthesizing method of the derivative of the acanthus ilicifolius L.alkaloid A is as following: the 4-hydroxylbenzoxazole-2-ketone reacts with halohydrocarbon or acyl halide for 1 to 3 hours under an alkali condition and in an ice-water bath of 0 to 10 DEG C; the reaction continues in water bath of 40 to 60 DEG C for 2 to 5 hours; then the temperature is increased for reflux and TLC is adopted for tracing till the disappearance of material point is detected; the reaction is stopped, the temperature is reduced to the room temperature, HCl is adopted for neutralizing to neutrality, the filtrate is filtered, condensed and dried to obtain solids; and the solids are washed, decolored and recrystallized to obtain the final product. The method for synthesizing the acanthus ilicifolius L.alkaloid A and the derivative thereof can be used for preparing anti-inflammatory and analgesic medicines and can avoid felling mangrove, thus protecting the mangrove resources.

Description

technical field [0001] The present invention relates to the preparation method of rat bovine alkaloid A and its derivatives with anti-inflammatory and analgesic activity. The compound of the present invention is used for treating and preventing inflammation and analgesia in mammals including human body. Background technique [0002] Existing anti-inflammatory and analgesic drugs mainly include non-steroidal anti-inflammatory drugs (hereinafter referred to as NSAIDs) such as aspirin, ibuprofen, and nimesulide. They have excellent anti-inflammatory, analgesic and antipyretic effects, and are widely used clinically in the treatment of acute and chronic pain and the step-by-step treatment of cancer pain. They are the second largest class of drugs after anti-infective drugs. Inflammatory NSAIDs have now become a class of therapeutic drugs with a large number of varieties and excellent anti-inflammatory, analgesic and anti-rheumatic effects. [0003] Many people around the world...

Claims

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Application Information

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IPC IPC(8): C07D263/58A61K31/423A61P29/00
Inventor 龙盛京韦贤陈永好郑广进李雪华彭兴李姝
Owner GUANGXI MEDICAL UNIVERSITY
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