1R-methyl-beta-tetrahydro carboline acyl-K(GRPAK)-RGDV, synthesis thereof, activity thereof and applications thereof

A -arg-gly-asp-val, methyl technology, applied in 1R-methyl-β-tetrahydrocarboline-K (GRPAK)-RGDV, its synthesis, activity and application fields, can solve the preparation difficulty , Sensitive to the reducing environment, difficult to preserve, etc.

Inactive Publication Date: 2018-12-04
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
View PDF4 Cites 4 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 1R-methyl-beta-tetrahydro carboline acyl-K(GRPAK)-RGDV, synthesis thereof, activity thereof and applications thereof
  • 1R-methyl-beta-tetrahydro carboline acyl-K(GRPAK)-RGDV, synthesis thereof, activity thereof and applications thereof
  • 1R-methyl-beta-tetrahydro carboline acyl-K(GRPAK)-RGDV, synthesis thereof, activity thereof and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1 Preparation of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester

[0017] 1 mL of concentrated sulfuric acid with a concentration of 98% was added dropwise to 800 mL of distilled water at 60° C., 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 first stirred at 60° C. for 12 h, and then 3 mL of concentrated ammonia water was added dropwise therein 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 pale yellow solid as 1R-methyl-1,2,3,4-tetrahydro-β-carboline-3S-carboxylate benzyl ester and 1S-methyl - Mixtures of benzyl 1,2,3,4-tetrahydro-β-carbolin...

Embodiment 2

[0018] Example 2 Preparation of N-Boc-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)

[0019] 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 (dichlorom...

Embodiment 3

[0022] Example 3 Preparation of Boc-1R-methyl-1,2,3,4-tetrahydro-β-carboline-3S-carboxylic acid (2)

[0023] Add 100mg Pd / C , and 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-1R-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] - .

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses 1R-methyl-1,2,3,4-tetrahydro-beta-carboline-3S-acyl-Lys(Gly-Arg-Pro-Ala-Lys)-Arg-Gly-Asp-Val which is shown in the description; a preparation method and antithrombotic activityof the 1R-methyl-1,2,3,4-tetrahydro-beta-carboline-3S-acyl-Lys(Gly-Arg-Pro-Ala-Lys)-Arg-Gly-Asp-Val are disclosed; functions of treating a rat who is in stoke for 24 hours are disclosed; and applications for preparing antithrombotic drugs and thrombolytic drugs and treating ischemic stroke drugs are also disclosed. The structural formula of the 1R-methyl-1,2,3,4-tetrahydro-beta-carboline-3S-acyl-Lys(Gly-Arg-Pro-Ala-Lys)-Arg-Gly-Asp-Val is shown in the description.

Description

technical field [0001] The present invention relates to 1R-methyl-1,2,3,4-tetrahydro-β-carboline-3S-acyl-Lys(Gly-Arg-Pro-Ala-Lys)-Arg-Gly-Asp- Val relates to its preparation method, relates to its antithrombotic activity, relates to its thrombolytic activity and relates to its effect on treating stroke rats for 24 hours, so the present invention relates to its use in preparing antithrombotic drugs, thrombolytic drugs and treating deficient Use of drugs in hemorrhagic stroke. 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...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/60A61K38/12A61P7/02
CPCA61K38/00C07K7/60
Inventor 彭师奇赵明王玉记吴建辉张筱宜桂林王晓珍
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap