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Coumarin derivative and its preparation method

A technology of hydroxycoumarins and compounds, applied in the field of biomedicine, can solve the problems of increasing myocardial infarction and the like

Inactive Publication Date: 2018-11-30
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Nonsteroidal anti-inflammatory drugs (NSAIDS) and selective cyclooxygenase-2 (COX-2) inhibitors are traditional drugs used to treat acute or chronic inflammatory diseases, but studies have found that NSAIDS can induce severe gastrointestinal Adverse reactions, including gastrointestinal bleeding and induced ulcers, while selective COX-2 inhibitors can increase the risk of myocardial infarction, sudden cardiac death and stroke in patients

Method used

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  • Coumarin derivative and its preparation method
  • Coumarin derivative and its preparation method
  • Coumarin derivative and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Embodiment 1 prepares 7-hydroxycoumarin-3-formic acid ethyl ester (2)

[0040] At a temperature of 90°C, weigh 2,4-dihydroxybenzaldehyde (0.500g, 3.60mmol) and measure diethyl malonate (0.70ml, 4.00mmol) into a 100ml eggplant bottle, dissolve in 95% In ethanol (20ml), the color of the solution was a reddish-brown transparent liquid at this time; piperidine (0.40ml, 4.00mmol) was added, the surface of the solution glowed green, and it began to reflux. After about 6 hours of reaction, the solution turned dark brown. Cooled to room temperature, concentrated under reduced pressure to red viscous, recrystallized from ethanol, and filtered to obtain compound 3 (0.758 g, 3.24 mmol), which was a light yellow solid with a yield of 90%. ESI-MS m / z 233 (M-1).

Embodiment 2

[0041] Embodiment 2 prepares 7-hydroxycoumarin-3-carboxylic acid (3)

[0042] At a temperature of 90°C, compound 3 (2.00g, 8.55mmol) was weighed and dissolved in water (20ml), concentrated hydrochloric acid (6ml) was added, and then refluxed for 8h. The reaction solution was cooled to room temperature, filtered and washed with water to obtain compound 4 (1.32 g, 6.41 mmol) as a light red solid with a yield of 75%. ESI-MS m / z 205 (M-1).

Embodiment 3

[0043] Example 3 Preparation of 7-hydroxycoumarin-3-formyl-β-propionic acid benzyl ester (4)

[0044] Weigh 3 (1.00g, 4.85mmol) and put it in a 100ml eggplant bottle, add tetrahydrofuran (30ml) under ice-bath cooling condition, add N-hydroxybenzotriazole (HOBt) (0.720g, 5.33mmol) successively, 1- (3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) (1.02 g, 5.33 mmol), reacted for 30 minutes. Compound Tos·β-alanine-OBzl (1.87g, 5.33mmol) dissolved in tetrahydrofuran (20ml) was added, and N-methylmorpholine (NMM) (0.60ml) was added dropwise to adjust the pH to 8. TLC detection was carried out throughout the reaction, and the reaction was complete in about 8 hours. Filter, concentrate to dryness under reduced pressure, add ethyl acetate (100ml) to dissolve the residue, add the solution to a 250ml separatory funnel, wash with saturated sodium bicarbonate aqueous solution (50mL×3), saturated sodium chloride aqueous solution Wash (50mL×3), 5% potassium bisulfate aq...

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Abstract

The invention relates to a coumarin derivative and a preparation method thereof. Specifically, the invention discloses novel 7-hydroxycoumarin-3-formyl-beta-alanyl aminoacyl-2-aminomethyl pyridine with anti-inflammatory activities, which is shown in a general formula (I), and in the general formula (I), AA is equal to Ala, Leu, Val, Met, Phe, Tyr and Asp(OBzl). The invention further relates to the preparation method of the novel 7-hydroxycoumarin-3-formyl-beta-alanyl aminoacyl-2-aminomethyl pyridine and further discloses an anti-inflammatory effect of the novel 7-hydroxycoumarin-3-formyl-beta-alanyl aminoacyl-2-aminomethyl pyridine. Therefore, the invention discloses a clinical application prospect of 7-hydroxycoumarin-3-formyl-beta-propionic acid modified by 2-aminomethyl pyridine and amino acid as an anti-inflammatory drug.

Description

Field of Invention [0001] The invention belongs to the field of biomedicine, in particular the invention relates to novel 7-hydroxycoumarin-3-formyl-β-alanylaminoacyl-2-aminomethylpyrimidine (9a-g) with anti-inflammatory activity Preparation method and its application. Background technique [0002] Inflammation is a protective defense response and a common pathway leading to many important human diseases, and is involved in human infection, tumors, cardiovascular and cerebrovascular diseases, Alzheimer's disease and nervous system diseases, allergic diseases, mental illness, etc. The occurrence and development of other important diseases. Clinically, anti-inflammatory drugs are the second most commonly used drugs, second only to anti-infective drugs. Typical reactions are redness, swelling, heat, pain, and dysfunction. [0003] Nonsteroidal anti-inflammatory drugs (NSAIDS) and selective cyclooxygenase-2 (COX-2) inhibitors are traditional drugs used to treat acute or chroni...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12A61K31/506A61P29/00
CPCC07D405/12
Inventor 张建伟程凯
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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