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1S-methyl-beta-tetrahydrocarbolineacyl-K(ARPAK)-RGDV, synthesis, activity and application thereof

A technology of -arg-gly-asp-val, methyl, applied in the direction of medical preparations containing active ingredients, drug combinations, peptide/protein components, etc., can solve the problems of sensitive reducing environment, difficult storage, difficult preparation, etc.

Inactive Publication Date: 2019-12-17
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

That is, the free radicals of 1,3-dioximidazoline are sensitive to the reducing environment, which is not only difficult to prepare, but also difficult to store

Method used

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  • 1S-methyl-beta-tetrahydrocarbolineacyl-K(ARPAK)-RGDV, synthesis, activity and application thereof
  • 1S-methyl-beta-tetrahydrocarbolineacyl-K(ARPAK)-RGDV, synthesis, activity and application thereof
  • 1S-methyl-beta-tetrahydrocarbolineacyl-K(ARPAK)-RGDV, synthesis, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Preparation of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)

[0020] 1 mL of concentrated sulfuric acid with a concentration of 98% was added dropwise to 800 mL of distilled water, and after stirring evenly, 10.0 g (34 mmol) of L-Trp-OBzl was added therein three times. Stir for five minutes to fully suspend L-Trp-OBzl and sulfuric acid aqueous solution. Afterwards, 10 mL of 40% acetaldehyde aqueous solution was added dropwise to the suspension. The reaction mixture was stirred for 12 h, and then 3 mL of concentrated ammonia water was added dropwise to adjust the pH of the reaction solution to 8. The reaction compound was allowed to stand for 1 h until the product was fully separated. The solid was filtered off and dried to yield 9.84 g (90%) of a light yellow solid as 1S-methyl-1,2,3,4-tetrahydro-β-carboline-3S-carboxylate benzyl ester and 1S-methyl - Mixtures of benzyl 1,2,3,4-tetrahydro-β-carboline-3S-carboxylates. ESI-MS(m / ...

Embodiment 2

[0021] Example 2 Preparation of N-Boc-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (2)

[0022] 9.84g (30.8mmol) 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester obtained in Example 1 was mixed with 20mLN,N-dimethylformamide ( DMF) dissolved. Add 6.98g (32.0mmol) (Boc) to the solution at 0°C 2 O. The resulting solution was adjusted to pH 12 with triethylamine and stirred at room temperature for 48 h. The reaction mixture was concentrated under reduced pressure to remove DMF. The residue was dissolved with 100 mL of ethyl acetate. The obtained ethyl acetate solution was washed successively with 5% potassium hydrogensulfate aqueous solution (50 mL×3) and saturated sodium chloride aqueous solution (50 mL×3). The separated ethyl acetate layer was dried over anhydrous sodium sulfate for 12 h, filtered, and the filtrate was concentrated under reduced pressure to obtain an oil. The oil was separated on a silica gel column (dichlor...

Embodiment 3

[0023] Example 3 Preparation of Boc-1S-methyl-1,2,3,4-tetrahydro-β-carboline-3S-carboxylic acid (3)

[0024] Add 100mg Pd / C. Stir to make a homogeneous suspension. The air in the reaction system was extracted under reduced pressure, hydrogen gas was introduced, and stirred at room temperature for 10 h. TLC (dichloromethane / methanol, 40 / 1) showed that N-Boc-1S-methyl-1,2,3,4-tetrahydro- β-carboline-3S-carboxylate benzyl ester completely disappeared. The Pd / C was removed by filtration, the filtrate was concentrated under reduced pressure, and the ESI-MS (m / e) of the obtained colorless powder was 329 [M-H] - .

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Abstract

The invention discloses 1S-methyl-1,2,3,4-tetrahydro-beta-carboline-3S-formyl-Lys(Ala-Arg-Pro-Ala-Lys)-Arg-Gly-Asp-Val as shown in the formula, its preparation method, its antithrombotic activity, itsthrombolytic activity, and its effect of treating rats with stroke for 24 hours. Therefore, the invention discloses application of the 1S-methyl-1,2,3,4-tetrahydro-beta-carboline-3S-formyl-Lys(Ala-Arg-Pro-Ala-Lys)-Arg-Gly-Asp-Val in preparation of antithrombotic drugs, thrombolytic drugs and ischemic stroke treatment drugs.

Description

technical field [0001] The present invention relates to 1S-methyl-1,2,3,4-tetrahydro-β-carboline-3S-formyl-Lys(Ala-Arg-Pro-Ala-Lys)-Arg-Gly-Asp-Val, It relates to its preparation method, relates to its antithrombotic activity, relates to its thrombolytic activity and relates to its effect in treating stroke rats for 24 hours, thus the present invention relates to its preparation of antithrombotic drugs, thrombolytic drugs and treatment of ischemic Use in stroke medicine. The invention belongs to the field of biomedicine. [0002] technical background [0003] 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/06C07K1/04A61K38/08A61P7/02A61P9/10
CPCA61K38/00A61P7/02A61P9/10C07K7/06
Inventor 赵明王玉记冯琦琦彭师奇田孝纲
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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