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4'-oxyacetyl-APAK-7-oxyacetyl-RGDV-isoflavone, and synthesis, activity and application thereof

A technology of -obzl-7-, oxyacetyl, which is applied in the direction of medical preparations containing active ingredients, tetrapeptide ingredients, drug combinations, etc., can solve the problem of inability to antagonize rat aortic strip relaxation, untreated ischemic stroke, Unsatisfactory and other issues

Inactive Publication Date: 2017-12-15
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1,3-Dioxy-2-[(4-oxoacetic acid)phenyl]-4,4,5,5-tetramethylimidazoline-ARPAK, 1,3-dioxy-2-[(4 -oxyacetic acid)phenyl]-4,4,5,5-tetramethylimidazoline-GRPAK and 1,3-dioxy-2-[(4-oxoacetic acid)phenyl]-4,4,5 , 5-Tetramethylimidazoline-QRPAK can detect the activity of scavenging O free radicals, OH free radicals and NO free radicals on the ESR instrument (i.e. paramagnetic resonance instrument), but in the internationally recognized evaluation model (for acetylcholine-induced relaxation of rat aortic strips)
1,3-Dioxy-2-[(4-oxoacetic acid)phenyl]-4,4,5,5-tetramethylimidazoline-ARPAK, 1,3-dioxy-2-[(4 -oxyacetic acid)phenyl]-4,4,5,5-tetramethylimidazoline-GRPAK and 1,3-dioxy-2-[(4-oxoacetic acid)phenyl]-4,4,5 , the least desirable property of 5-tetramethylimidazoline-QRPAK is that it has no therapeutic effect on ischemic stroke

Method used

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  • 4'-oxyacetyl-APAK-7-oxyacetyl-RGDV-isoflavone, and synthesis, activity and application thereof
  • 4'-oxyacetyl-APAK-7-oxyacetyl-RGDV-isoflavone, and synthesis, activity and application thereof
  • 4'-oxyacetyl-APAK-7-oxyacetyl-RGDV-isoflavone, and synthesis, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 prepares 4', 7-methyl dioxyacetate-isoflavones (1)

[0021] Dissolve 20.19g (79.5mmol) of daidzein in 300mL of tetrahydrofuran (THF), add 87.8g (635.9mmol) of potassium carbonate, activate for 20 minutes, add 43.59mL (320mmol) of ethyl bromoacetate, and heat at 45°C in an oil bath Respond for 5 days. TLC monitoring: (dichloromethane:methanol=20:1) to monitor the reaction process, after the reaction is complete, the reaction solution is settled and filtered, the filtrate is decompressed to remove THF, and a large amount of petroleum ether is added to grind to remove excess ethyl bromoacetate. The obtained solid was dissolved by adding methanol, found to be slightly soluble, heated at 45° C., filtered while hot, and dried in the air. The filtrate was recrystallized by cold and heat, filtered, and the solid was collected to obtain 20.71 g (61.2%) of the title compound. ESI - -MS(m / e):397[M-H] - .

Embodiment 24

[0022] Embodiment 24', 7-dioxyacetic acid-isoflavones (2)

[0023]Dissolve 5.75g (13.5mmol) of methyl 4',7-dioxyacetate-isoflavone (1) in 100mL methanol (slightly soluble), add 2N NaOH, adjust the pH value of the solution to 12, the solid gradually dissolves, and After reacting for 4 hours, TLC (dichloromethane: methanol: glacial acetic acid = 20:1:2 drops) monitored the reaction process, the raw material point disappeared, and a large amount of white solid was precipitated after adding saturated potassium bisulfate solution to adjust the pH value of the solution to 1-2 , adding a large amount of water to dissolve the salt, then filtered, and the filter cake was washed with water repeatedly, and the solid was collected by air drying to obtain 4.60 g (92.2%) of the title compound. ESI - -MS(m / e):369[M-H] - .

Embodiment 3

[0024] Example 3 Preparation of 4'-oxyacetyl--Ala-Pro-Ala-Lys(Z)-OBzl-7-oxyacetic acid-isoflavones (3)

[0025] Dissolve 1.19g (3.2mmol) of 4',7-dioxyacetic acid-isoflavone (2) in 80mL of anhydrous N,N-dimethylformamide (DMF), and add 100mg of 4-dimethylaminopyridine (DMAP ) and 0.80g (3.9mmol) dicyclohexylcarbodiimide (DCC), after activation for 20 minutes, add HCl Ala-Pro-Ala-Lys (Z) with NMM to adjust the pH value to 8-9 under ice-cooling -OBzl 1.06g (3.9mmol), and adjust the pH value to 8-9 with NMM, after reacting for 18h, dry DMF, dissolve in dichloromethane, filter, separate and purify by column chromatography (dichloromethane / methanol), obtain 1.90 g (60.9%) of the title compound. ESI - -MS(m / e):960[M-H] - .

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Abstract

The invention discloses 4'-oxyacetyl-Ala-Pro-Ala-Lys-7-oxyacetyl-Arg-Gly-Asp-Val-isoflavone, a preparation method thereof, antithrombotic activity thereof, thrombolytic activity thereof, cerebral-thrombus-treating activity thereof, and free-radical-removing activity thereof. The invention discloses an application of 4'-oxyacetyl-Ala-Pro-Ala-Lys-7-oxyacetyl-Arg-Gly-Asp-Val-isoflavone to prepare antithrombotic medicines, thrombolytic medicines, cerebral-thrombus-treating medicines, and free-radical-removing medicines.

Description

technical field [0001] The present invention relates to 4'-oxyacetyl-Ala-Pro-Ala-Lys-7-oxyacetyl-Arg-Gly-Asp-Val-isoflavone, to its antithrombotic activity and to its thrombolytic activity, to its The activity of treating cerebral thrombosis involves its activity of scavenging free radicals, so the present invention relates to its application in the preparation of antithrombotic drugs, thrombolytic drugs, drugs for treating cerebral thrombosis and free radical scavenging drugs. The invention belongs to the field of biomedicine. Background technique [0002] Ischemic stroke is a relatively common and serious cerebrovascular disease, characterized by high incidence, high mortality, high disability rate and high recurrence rate. At present, the clinical treatment of ischemic stroke faces the reality that there is no effective drug, especially for patients with stroke lasting more than 4 hours, either dying or being disabled. It is an important clinical need to invent drugs th...

Claims

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Application Information

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IPC IPC(8): C07K5/11A61K38/07A61P7/02A61P39/06
CPCA61K38/00C07K5/1019
Inventor 彭师奇赵明吴建辉王玉记张帅
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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