1-(4-hydroxy-3-methoxycarbonyl)-beta-carboline-3-formyl tryptophyl amino acid benzyl ester, and synthesis and application thereof

A technology of tryptophan benzyl ester and methoxycarbonyl, which is applied in the field of biomedicine and can solve problems such as no obvious progress

Inactive Publication Date: 2013-06-19
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many domestic researchers have modified the structure of β-carboline compounds, there is no significant progress

Method used

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  • 1-(4-hydroxy-3-methoxycarbonyl)-beta-carboline-3-formyl tryptophyl amino acid benzyl ester, and synthesis and application thereof
  • 1-(4-hydroxy-3-methoxycarbonyl)-beta-carboline-3-formyl tryptophyl amino acid benzyl ester, and synthesis and application thereof
  • 1-(4-hydroxy-3-methoxycarbonyl)-beta-carboline-3-formyl tryptophyl amino acid benzyl ester, and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1 prepares methyl 5-formylsalicylate

[0020] 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 h, monitored by TLC until the raw material spots disappeared, stopped the reaction and cooled down to room temperature, transferred the reaction mixture to a 100 mL eggplant-shaped bottle, adjusted the pH value to 8 with concentrated ammonia water, and reduced the reaction mixture to Concentrate to dryness under reduced pressure, and add a large amount of ethyl acetate to dissolve the residue. The ethyl acetate layer was sequentially washed with saturated NaHCO 3 solution and saturated NaCl solution were washed three times each, and then washed with anhydrous NaCl 2 SO 4 Dry for 2 hours, filter, and concentrate the filtrate to dryness under reduced pressure. After standing at room temperature overnight, crystals precipitate out to o...

Embodiment 2

[0021] Embodiment 2 prepares L-tryptophan benzyl ester

[0022] 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, add 400mL of anhydrous ether to the reaction bottle under stirring in an ice bath, at this time, a colorless solid precipitates, stir After overnight filtration, the colorless solid was suspended with 200mL ethyl acetate and 10mL water, and the pH value of the solution was adjusted to about 8 with triethylamine. 3 solution and saturated NaCl solution were washed three times each. Ethyl acetate layer with anhydrous Na 2 SO 4 It was dried for 2 h, filtered, and the filtrate was concentrated under reduced pressure to obtain 12.85 g (89.2%) of the ti...

Embodiment 3

[0023] Example 3 Preparation of 1-(4-hydroxyl-3-methoxycarbonyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)

[0024] Add 100mL CH to a 250mL eggplant-shaped bottle 2 Cl 2 and 10mL TFA, 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 turns reddish after a few minutes After 2 days, the reaction solution turned black. Slowly add concentrated ammonia water dropwise under stirring in an ice bath to adjust the pH value of the reaction solution to 8. The reaction mixture was allowed to stand for liquid separation, and the separated CH 2 Cl 2 Layers were sequentially washed with saturated NaHCO 3 solution and saturated NaCl solution were washed three times, CH 2 Cl 2 Anhydrous Na 2 SO 4 Dry for 2 h, filter, and concentrate the filtrate to dryness under alkaline pressure to obtain 14.59 g (80%) of the title compound as a yellow solid. ESI-MS(m / e):...

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Abstract

The invention discloses 16 pseudopeptides represented by a general formula I (wherein in the general formula I, AA is equal to L-Ala, Gly, L-Leu, L-Ile, L-Val, L-Phe, L-Asp, L-Glu, L-Ser,L-Thr, L-Asn, L-Trp, L-Tyr, L-Met, L-Pro and Lys residue and further discloses a preparation method and application thereof. The pseudopeptides show excellent in-vitro and in-vivo anti-tumor effects in a cell model and an S180 tumor-bearing mouse model and an excellent anti-inflammatory effect in a mouse ear swelling model.

Description

technical field [0001] The present invention relates to general formula I (in the formula AA=L-Ala, Gly, L-Leu, L-Ile, L-Val, L-Phe, L-Asp, L-Glu, L-Ser, L-Thr, L 16 pseudopeptides of -Asn, L-Trp, L-Tyr, L-Met, L-Pro and Lys residues), their preparation methods and uses. The compound of the present invention shows excellent anti-tumor effects in vivo and in vitro on cell models and S180 tumor-bearing mouse models, and shows excellent anti-inflammatory effects on mouse ear swelling models. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Malignant tumors seriously threaten human health. According to the data published by WHO, the incidence of cancer worldwide will increase by 50% in 2020, and the number of new cancer patients worldwide will reach 15 million each year. In the research of anti-cancer drugs, searching for natural anti-tumor active ingredients from organisms has become an important way to find new lead compounds. Of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/097A61K38/06A61P35/00A61P29/00
Inventor 彭师奇赵明王玉记吴建辉李珊
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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