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Imidazopyridine-6-formyl-Met-AA-OBzl, synthesis, activity and applications thereof

A technology of imidazo and pyridine, which is applied in the field of antithrombotic and anti-inflammatory drugs, and can solve problems such as worsening prognosis of tumor patients and endangering health

Inactive Publication Date: 2016-01-20
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Not only endangering health, but also worsening the prognosis of tumor patients

Method used

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  • Imidazopyridine-6-formyl-Met-AA-OBzl, synthesis, activity and applications thereof
  • Imidazopyridine-6-formyl-Met-AA-OBzl, synthesis, activity and applications thereof
  • Imidazopyridine-6-formyl-Met-AA-OBzl, synthesis, activity and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of Example 1 Compound 6S-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid (1)

[0020] Mix 10.00g (64.5mmol) L-histidine, 30mL water in a 100mL eggplant bottle, add 2mL concentrated sulfuric acid drop by drop with a constant pressure funnel under ice bath, with the addition of concentrated sulfuric acid, the raw material gradually dissolves, and wait until it is completely dissolved Finally, 10 mL of 40% formaldehyde solution was added to the reaction liquid, and reacted at 65° C. for 5 hours in a microwave accelerated reaction apparatus. After the reaction was completed, concentrated ammonia water was slowly added dropwise in an ice bath to adjust the pH of the solution to 6-7, a large amount of white precipitates were precipitated, and filtered under reduced pressure to obtain 10.76 g (99.2%) of a colorless solid. ESI-MS(m / z): 168[M+H] + .

Embodiment 2

[0021] Example 2 Preparation of Compound 6S-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester (2)

[0022] Add 15.6mL of methanol to a 100mL eggplant bottle under ice-cooling, slowly add 1.56mL of thionyl chloride dropwise with a constant pressure funnel under ice-cooling, and add 1.00g (6mmol) of 6S-4,5,6,7-tetrahydro -3H-imidazo[4,5-c]pyridine-6-carboxylic acid (2), after 3 days of reaction at room temperature, the reaction was complete as monitored by TLC, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol and concentrated under reduced pressure. This operation was repeated 3 times to obtain a white foamy solid, which was then drained with diethyl ether and repeated 3 times to obtain a colorless powder, and finally recrystallized from methanol / diethyl ether to obtain 0.58 g (53%) of the title compound as a colorless solid. ESI-MS(m / z)181[M+H] + .

Embodiment 3

[0023] Preparation of Example 3 Compound 3H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester (3)

[0024] Add 1.1g (6.1mmol) 6S-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester (3) in a 100mL eggplant bottle under ice-cooling, add DMF dissolves. 1 mL of triethylamine was added dropwise to the solution to adjust the pH to 8, and 1.2 g (7.6 mmol) of potassium permanganate was added three times. After reacting for 6 hours, TLC monitored the completion of the reaction. The reactant was blown to dryness, and the obtained black solid was dissolved in 1N HCl solution, and 2N NaOH solution was added dropwise in ice bath to adjust the pH to 7, and a large amount of colorless solid was precipitated. The solid was purified on a silica gel column eluting with dichloromethane / methanol to afford 0.68 g (63.2%) of the title compound as a colorless solid. ESI-MS(m / z)177[M+H] + .

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Abstract

The present invention discloses six kinds of 3H-imidazo[4,5-c]pyridine-6-formyl-Met-AA-benzyl esters, preparation methods and antithrombotic activities of thereof, and further discloses anti-inflammatory activities on ICR mice, such that the present invention discloses double applications of the 3H-imidazo[4,5-c]pyridine-6-formyl-Met-AA-benzyl esters in anti-thrombus and anti-inflammation.

Description

field of invention [0001] The present invention relates to 6 kinds of 3H-imidazo[4,5-c]pyridine-6-formyl-Met-AA-OBzl represented by general formula I, to their preparation method, to their antithrombotic activity on SD rats and their anti-inflammatory activity on ICR mice, thus the present invention relates to its use as an antithrombotic and anti-inflammatory drug. The invention belongs to the field of biomedicine. Background technique [0002] Thrombotic disease is a cardiovascular and cerebrovascular disease that seriously threatens human health. Every year, 3‰ of people will suffer from thrombotic disease to varying degrees, and its morbidity and mortality are high. In addition, thrombus is an important complication of cancer patients, which can worsen the prognosis of cancer patients. Inflammation is a precursor or complication of many serious diseases. For example, inflammation is not only a precancerous lesion, but also an important complication of cancer patients....

Claims

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Application Information

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IPC IPC(8): C07K5/097A61K38/06A61P7/02A61P29/00
Inventor 赵明彭师奇吴建辉王玉记陈海燕刘文超李骏
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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