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YIGSR-modified beta-carboline, preparation, nano-structure, activity and application thereof

A carboline and reactive technology, applied in the field of anti-inflammatory and anti-thrombotic effects, can solve the problems of anti-tumor, anti-inflammatory, anti-thrombotic and anti-tumor adhesion, invasion and migration compounds

Inactive Publication Date: 2016-01-27
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the inventor has devoted a lot of research effort and screened hundreds of compounds, no compound with anti-tumor, anti-inflammation, anti-thrombotic and anti-tumor adhesion, invasion and migration effects has been obtained

Method used

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  • YIGSR-modified beta-carboline, preparation, nano-structure, activity and application thereof
  • YIGSR-modified beta-carboline, preparation, nano-structure, activity and application thereof
  • YIGSR-modified beta-carboline, preparation, nano-structure, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1 prepares methyl 5-formylsalicylate

[0030] Weigh 1.660g (10.0mmol) of 5-formylsalicylic acid in a microwave reaction tank, add 25mL of methanol and 1mL of concentrated H 2 SO 4 , reacted in a microwave reactor at 90°C for 2 hours, monitored by TLC until the raw material spots disappeared, stopped the reaction and cooled down to room temperature, transferred the reaction solution to a 100mL eggplant-shaped bottle, adjusted the pH value to 7-8 with concentrated ammonia water, and reacted After the solution was concentrated to dryness under reduced pressure, a large amount of ethyl acetate was added to dissolve it, and the ethyl acetate layer was successively washed with saturated NaHCO 3 , saturated NaCl three times each, and then washed with anhydrous NaCl 2 SO 4 It was dried for 2 hours, filtered, and concentrated under reduced pressure. After standing at room temperature overnight, crystals precipitated to obtain 1.635 g (90.8%) of the title compound a...

Embodiment 2

[0031] Embodiment 2 prepares L-tryptophan benzyl ester

[0032]Weigh 15.0g (44.4mmol) of polyphosphoric acid in a 500mL eggplant-shaped bottle, add 80mL of benzyl alcohol, and dissolve it in an oil bath at 50°C. After the temperature of the solution rises to 75°C, weigh 10g (49.0mmol) of L - Add tryptophan to it, react at 75°C for 48 hours, use TLC to monitor until the raw material spots disappear, stop the reaction and cool down, pour 400mL of anhydrous ether into the reaction bottle under stirring in an ice bath, at this time a white solid precipitates, stir After overnight, filter it, suspend the white solid with 200mL ethyl acetate and 10mL water, adjust the pH value of the solution to about 8 with triethylamine, the solution becomes clear, let it stand for liquid separation, and wash the separated ester layer with saturated NaHCO 3 , saturated NaCl three times each, and the ethyl acetate layer was washed with anhydrous NaCl 2 SO 4 Dry for 2 h, filter, and concentrate to...

Embodiment 3

[0033] Example 3 Preparation of 1-(4-hydroxyl-3-methoxycarbonylphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)

[0034] Add 100mLCH to a 250mL eggplant-shaped bottle 2 Cl 2 And 10mLTFA, after stirring evenly, weigh 11.76g (40.0mmol) L-tryptophan benzyl ester and 7.92g (44.0mmol) methyl 5-formylsalicylate and add it, and the reaction solution becomes reddish after a few minutes. After 2 days, the reaction solution turned black. Slowly add concentrated ammonia water dropwise under ice-bath stirring to adjust the pH value of the reaction solution to 8. The reaction solution was allowed to stand for liquid separation, and the CH 2 Cl 2 Layers were sequentially washed with saturated NaHCO 3 and saturated NaCl three times each, CH 2 Cl 2 Anhydrous Na 2 SO 4 Dry for 2 h, filter, and concentrate to dryness under reduced pressure to give 14.59 g (80%) of the title compound as a yellow solid. ESI-MS(m / e): 457[M+H] + .

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Abstract

The invention discloses a compound 1-(4-hydroxy-3-methoxycarbonylphenyl)-beta-carboline-3-formyl-Tyr-Ile-Gly-Ser-Arg, wherein YIGSR is formally short forTyr-Ile-Gly-Ser-Arg. The invention also discloses a preparation method of the compound, a nano-structure of the compound, an anti-tumor effect of the compound, an effect of the compound in inhibiting adhesion, invasion and migration of tumor cells, further discloses antiinflammatory and antithrombotic effects of the compound and expounds an application of the compound in medical science.

Description

technical field [0001] The present invention relates to 1-(4-hydroxy-3-methoxycarbonylphenyl)-β-carboline-3-formyl-Tyr-Ile-Gly-Ser-Arg. The official abbreviation for Tyr-Ile-Gly-Ser-Arg is YIGSR. It relates to its preparation method, its nanostructure, its in vivo and in vitro anti-tumor effects, its anti-tumor cell adhesion, invasion and migration effects, and its anti-inflammatory and antithrombotic effects. The invention belongs to the field of biomedicine. technical background [0002] Malignant tumors seriously threaten human health. In addition to the poor prognosis of cancer patients, the inflammation, thrombus and metastasis of malignant tumors further worsen the prognosis of patients. For example, more than 90% of malignant tumor patients died of tumor metastasis. Tumor metastasis depends on four factors: 1) microthrombosis forms on the surface of tumor cells, escapes macrophage phagocytosis, and migrates to the distal end through blood circulation; 2) tumor cel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/06C07K1/02A61K38/08A61P35/00A61P29/00A61P7/02B82Y30/00
Inventor 赵明彭师奇王玉记吴建辉李珊
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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