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4'-oxyacetyl-Ala-5-hydroxyl-7-oxyacetyl-RGDV-isoflavone, and synthesis, activity and application thereof

A technology of hydroxyisoflavone and oxyacetyl, which is applied in the field of treatment of cerebral thrombosis, can solve the problems of inability to antagonize rat aortic strip relaxation, unsatisfactory, untreated ischemic stroke, etc.

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-Ala-5-hydroxyl-7-oxyacetyl-RGDV-isoflavone, and synthesis, activity and application thereof
  • 4'-oxyacetyl-Ala-5-hydroxyl-7-oxyacetyl-RGDV-isoflavone, and synthesis, activity and application thereof
  • 4'-oxyacetyl-Ala-5-hydroxyl-7-oxyacetyl-RGDV-isoflavone, and synthesis, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Preparation of 4', 7-methyl dioxyacetate-5-hydroxy isoflavone (1)

[0020] Dissolve 11.69g (43.3mmol) of genistein in 200mL of tetrahydrofuran (THF), add 46.92g (340mmol) of potassium carbonate to the reaction solution, activate it for 20 minutes, add 14mL (87mmol) of ethyl bromoacetate, and place in a 45°C oil bath Under heating reaction for 5 days. The progress of the reaction was monitored by TLC (dichloromethane:methanol=20:1). After the reaction is complete, the reaction liquid is settled and filtered, the filtrate is decompressed to remove THF, and a large amount of petroleum ether is added to grind and wash to remove excess ethyl bromoacetate. The obtained solid is dissolved by adding methanol and found to be slightly soluble. After hot filtration, the solid was air-dried, and the filtrate was recrystallized by cold and heat, and the white solid was collected by filtration to obtain 11.70 g (61.1%) of the title compound. ESI - -MS(m / e):413[M-H] - . ...

Embodiment 2

[0021] Example 2 Preparation of 4', 7-dioxyacetic acid-5-hydroxy isoflavone (2)

[0022] Take 5.17g (12.5mmol) of methyl 4',7-dioxyacetate-5-hydroxyisoflavone (1) and add 100mL of methanol to make it slightly soluble. Add 2N NaOH aqueous solution dropwise to the reaction solution to adjust the pH value of the solution to 12. The solid gradually dissolved, and after reacting at room temperature for 4 hours, TLC (dichloromethane:methanol:glacial acetic acid=20:1:2 drops) monitored the reaction progress, and the raw material point disappeared, and the pH value of the solution was adjusted to 1-2 by adding saturated potassium bisulfate solution. A large amount of white solid was precipitated, and a large amount of water was added to dissolve the salt, and then filtered, and the filter cake was washed with water repeatedly, and the white solid was collected by drying to obtain 4.10 g (84.2%) of the title compound. ESI - -MS(m / e):385[M-H] - .

Embodiment 3

[0023] Embodiment 3 prepares 4'-oxyacetyl-Ala-OBzl-5-hydroxyl-7-oxyacetic acid-isoflavones (3)

[0024] Dissolve 1.59g (4.1mmol) of 4',7-dioxyacetic acid-5-hydroxyisoflavone (2) in 80mL of anhydrous N,N-dimethylformamide (DMF), and add to the reaction solution under ice-cooling Add 100mg (8.2mmol) 4-dimethylaminopyridine (DMAP) and 1.02g (4.9mmol) dicyclohexylcarbodiimide (DCC), activate for 20 minutes to obtain solution a; take 1.06g (4.9mmol) HCl A -OBzl was dissolved with anhydrous DMF and the pH value was adjusted to 8, the obtained solution was added to solution a, and the pH value of the reaction solution was adjusted to 8-9 using NMM, after 18 hours of reaction, the DMF was dried, and the obtained residue It was dissolved in dichloromethane, filtered, and the filtrate was separated and purified by column chromatography (dichloromethane / methanol) to obtain 1.50 g (66.8%) of the title compound. ESI - -MS(m / e):546[M-H] - .

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Abstract

The invention discloses 4'-oxyacetyl-Ala-5-hydroxyl-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-5-hydroxyl-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-5-hydroxyl-7-oxyacetyl-Arg-Gly-Asp-Val-isoflavone, to its antithrombotic activity and to its thrombolytic activity, to its therapeutic brain The thrombus activity relates to 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 that a...

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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