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9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters, and synthesis, antitumor activity and application thereof

A formyl amino acid benzyl ester and methoxymethyl technology, which can be used in antitumor drugs, dipeptide components, drug combinations, etc., and can solve the problems of high toxicity of β-carboline

Inactive Publication Date: 2014-12-24
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This mode of action makes β-carbolines highly toxic

Method used

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  • 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters, and synthesis, antitumor activity and application thereof
  • 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters, and synthesis, antitumor activity and application thereof
  • 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters, and synthesis, antitumor activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1 prepares 3S-9-hydroxymethyl-tetrahydro-β-carboline-3-carboxylic acid (1)

[0018] Add 6 drops of 98% concentrated sulfuric acid to 800ml of distilled water, add 10g of L-tryptophan, stir to dissolve completely, add 40ml of formaldehyde solution, stir for 48 hours, adjust the pH to 7 with ammonia water, let it stand for 30min, there are a lot of colorless solids sink out. Suction filtration afforded 11 g (90%) of the title compound as a colorless solid. ESI-MS(m / e)246[M-H] - .

Embodiment 2

[0019] Example 2 Preparation of 3S-9-methoxymethyl-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2)

[0020] Slowly add 8ml of thionyl chloride dropwise to 120ml of methanol with stirring in an ice bath, and continue stirring for 30min after the dropwise addition is complete. Add 11 g of 3S-9-hydroxymethyl-tetrahydro-β-carboline-3-carboxylic acid (1) to the mixture, and stir for 48 hours. Suction filtration afforded 6 (50%) title compounds as pale yellow solids. ESI-MS(m / e)274[M-H] - .

Embodiment 3

[0021] Example 3 Preparation of 9-methoxymethyl-β-carboline-3-carboxylic acid methyl ester (3)

[0022] Add 300ml of N,N-dimethylformamide (DMF) to 5g of 3S-9-methyl-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2), stir in an ice bath, and add slowly in batches 6g potassium permanganate. Stir at room temperature for 48 hours, add 300ml of ethanol, and stir for 3 hours. Filtration, the filtrate was concentrated under reduced pressure, the obtained reddish-brown solid was dissolved in ethanol, the insoluble matter was filtered off, the obtained light yellow transparent liquid was concentrated to dryness under reduced pressure, and the obtained yellow solid was purified by column chromatography (petroleum ether: acetone=4 : 1), 2.3 g (45%) of the title compound as a colorless solid. ESI-MS(m / e)270[M-H] - .

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PUM

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Abstract

The invention discloses 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters, and synthesis, an antitumor activity and an application thereof. The invention discloses 16 kinds of 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters represented by the formula I, wherein in the formula I, AA is selected from the group consisting of L-Leu, L-Glu, L-Val, L-Trp, L-Arg, L-Tyr, L-Met, L-Phe, L-Ala, L-Gly, L-His, L-Asp, L-Ile, L-Lys, L-Ser and L-Thr residues. The invention discloses the preparation method of the 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters. The invention discloses an inhibitory effect of the 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters on proliferation of HL60 (human promyelocytic leukemia cells), K562 (human chronic myelocytic leukemia cells), HeLa (epithelial-derived cervical cancer cells), HepG2 (hepatocellular carcinoma cells) and HT-29 (human colon cancer cells). The invention further discloses an inhibitory effect of the 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters on tumor growth of S180-burdened mice. Therefore, the invention discloses clinical application prospects of the 16 kinds of 9-methoxymethyl-beta-carboline-3-formyl amino acid benzyl esters represented by the formula I as antitumor drugs.

Description

field of invention [0001] The present invention relates to 16 kinds of 9-methoxymethyl-β-carboline-3-formyl amino acid benzyl esters, to their preparation, to their effects on the proliferation of five strains of tumor cells K562, HL60, Hela, HepG2, and HT-29 Inhibitory activity, and further implicated in their inhibition of tumor growth in S180-bearing mice. Therefore, the present invention relates to the clinical application prospects of 16 kinds of 9-methoxymethyl-β-carboline-3-formyl amino acid benzyl esters as antitumor drugs. The invention belongs to the field of biomedicine. Background technique [0002] Tumor is a new organism formed by the body under the action of various tumorigenic factors, cells in local tissues lose control of growth at the gene level, resulting in monoclonal abnormal proliferation. Worldwide, tumors seriously endanger human health, affect the quality of human life, and become one of the most important causes of death. One of the important so...

Claims

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Application Information

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IPC IPC(8): C07K5/078A61K38/05A61P35/00A61P35/02
Inventor 赵明彭师奇王玉记吴建辉张攀
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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