Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Fatty amino acid modified indole ethanol derivative, synthesis, activities and applications thereof

A technology of indole and ethoxyacetyl, which is used in the preparation of antitumor drugs, 1--3-indole, and the field of anti-inflammatory activity, and can solve problems such as toxic and side effects

Active Publication Date: 2019-01-01
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
View PDF4 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

That is to say, this type of bis-indole alcohol benzyl amino acid faces a greater risk of toxic and side effects
The second point of dissatisfaction is that the minimum effective dose for them to play the triple role of anti-tumor, anti-tumor metastasis and anti-inflammation is 0.2μmol / kg, which is too high

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
  • Fatty amino acid modified indole ethanol derivative, synthesis, activities and applications thereof
  • Fatty amino acid modified indole ethanol derivative, synthesis, activities and applications thereof
  • Fatty amino acid modified indole ethanol derivative, synthesis, activities and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1 Preparation of 1-ethoxycarbonylmethyl-3-ethoxycarbonylmethoxyethyl-indole (1)

[0016] Slowly add 2.98g (4mmol, 60%) NaH to a solution of 5.00g (31mmol) indole alcohol and 50mL anhydrous tetrahydrofuran (THF) at room temperature, and slowly add 17.22mL (5mmol) ethyl bromoacetate after stirring for 30 minutes , heated at 80°C for 48 hours. TLC (petroleum ether / ethyl acetate, 3 / 1) showed the reaction was complete. Heating was stopped and the reaction mixture was cooled to room temperature. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate, 3 / 1) to obtain 1.54 g (15%) of the title compound as a yellow syrup. ESI-MS(m / e):334[M+H] + .

Embodiment 2

[0017] Embodiment 2 prepares 1-carboxymethyl-3-carboxymethoxy ethyl indole (2)

[0018] 1.31 g (3.9 mmol) of 1-ethoxycarbonylmethyl-3-ethoxycarbonylmethoxyethyl-indole (1) was dissolved in 10 mL of methanol under ice cooling. A 2N NaOH aqueous solution was added dropwise to the obtained solution to adjust the pH of the solution to 12. After stirring for 5 hours, TLC (petroleum ether / ethyl acetate, 3 / 1) showed that the reaction was complete. The reaction mixture was saturated with KHSO 4 The pH of the aqueous solution was adjusted to 7, concentrated under reduced pressure, the residue was extracted 3 times with 15 mL ethyl acetate, and the aqueous layer was washed with saturated KHSO 4 The aqueous solution was adjusted to pH 4 and extracted 3 times with 15 mL of ethyl acetate. The separated aqueous layer continued to be saturated with KHSO 4 Adjust the pH of the aqueous solution to 2, extract 3 times with 15 mL ethyl acetate and combine the separated ethyl acetate layers, wa...

Embodiment 3

[0019] Example 3 Preparation of 1-(acetyl-Ala-OBzl)-3-(ethoxyacetyl-Ala-OBzl) indole (3a)

[0020] A solution of 0.55 g (2.0 mmol) of 1-carboxymethyl-3-carboxymethoxyethyl-indole (2), 0.54 g (4.0 mmol) of N-hydroxybenzotriazole and 10 mL of anhydrous THF was stirred After 30 minutes, reaction solution A was obtained. 0.82 g (4.0 mmol) of dicyclohexylcarbodiimide was dissolved in 5 mL of anhydrous THF to obtain a reaction solution B. Under ice-cooling, the reaction solution B was slowly added dropwise to the reaction solution A, and stirred for 30 minutes. Then, a solution of 1.72 g (8.0 mmol) of HCl·Ala-OBzl and 15 mL of anhydrous THF was added thereto. The reaction mixture was adjusted to pH 9 with N-methylmorpholine and stirred at room temperature for 10 hours. TLC (CH 2 Cl 2 / CH 3 OH, 30 / 1, plus 3 drops of acetic acid) showed completion of the reaction. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was dissol...

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 present invention discloses 1-(acetyl-AA-OBzl)-3-(ethoxyacetyl-AA-OBzl) indole represented by the following formula (wherein AA is L-Ala residue, Gly residue, L-IIe residue, L-Val residue and L-Leu residue), a preparation method, antitumor activity, anti-tumor-metastasis activity and anti-inflammatory activity thereof, such that the present invention discloses applications of the 1-(acetyl-AA-OBzl)-3-(ethoxyacetyl-AA-OBzl) indole in preparation of antitumor drugs, anti-tumor-metastasis drugs and anti-inflammatory drugs. The formula is defined in the specification.

Description

technical field [0001] The present invention relates to 1-(acetyl-AA-OBzl)-3-(ethoxyacetyl-AA-OBzl) indole, to their preparation process, to their antitumor activity, to their antitumor metastasis activity, and Involving their anti-inflammatory activity, so the present invention relates to their application in the preparation of anti-tumor drugs, anti-tumor metastasis drugs and anti-inflammatory drugs. The invention belongs to the field of biomedicine. Background technique [0002] Malignant tumors seriously threaten human health. Lung cancer is one of the most aggressive human cancers. For patients with advanced lung cancer, usually 10%-15% of them can only survive for 5 years. This difficult situation has not improved significantly over the past 30 years. In many clinical cases, lung cancer has metastasized to surrounding tissues before being diagnosed. Tumor metastasis, especially tumor lung metastasis is the greatest risk of death in cancer patients. So far, there ...

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): C07K5/078A61K38/05A61P35/00A61P29/00
CPCC07K5/06139A61K38/00
Inventor 赵明彭师奇王玉记吴建辉甘太平吴晨
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com