[Beta]-carboline modified by Trp-Trp-Trp hexapeptide, and preparation, nano structure, activity and application thereof

A technology of trp-trp-trp-leu-asp-val and carboline, applied in the field of preparation of antitumor drugs, can solve the problems of not obtaining compounds with antitumor and antitumor metastasis effects

Inactive Publication Date: 2016-02-10
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • [Beta]-carboline modified by Trp-Trp-Trp hexapeptide, and preparation, nano structure, activity and application thereof
  • [Beta]-carboline modified by Trp-Trp-Trp hexapeptide, and preparation, nano structure, activity and application thereof
  • [Beta]-carboline modified by Trp-Trp-Trp hexapeptide, and preparation, nano structure, activity and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1 prepares L-tryptophan methyl ester hydrochloride (1)

[0030] Measure 100mL of methanol into a 250mL eggplant bottle, add 25.5mL of SOCl to the eggplant bottle under ice bath 2 , Plug the drying tube, and after stirring for 30min, add 20.400g (100mmol) of L-tryptophan which has been weighed. Stir at room temperature for 48 hours, monitor the reaction by TLC, stop the reaction when the raw material point disappears, concentrate under reduced pressure to remove the solvent, add 30 mL of methanol, mix well, concentrate again under reduced pressure to remove the solvent, and repeat the operation twice. Finally, 50 mL of diethyl ether was added, suspended for 30 min, filtered, and the filter cake was dried and weighed to obtain 22.98 g (90.2%) of the target compound as a gray powder. ESI-MS(m / e): 219[M+H] + .

Embodiment 2

[0031] Example 2 Preparation of (3S)-1-(4-isopropylphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2)

[0032] Measure 100mL of distilled water into a 250mL eggplant bottle, add 10mL of TFA under ice bath, stir for 5 minutes, add 20.320g (80mmol) of L-tryptophan methyl ester hydrochloride, stir until dissolved, add 10.672g (88mmol) of p-cymene Formaldehyde was stirred at room temperature for 24 h, and the starting point disappeared as monitored by TLC, and the reaction was terminated. The reactant was filtered under reduced pressure, the filter cake was dissolved with ethyl acetate, and saturated NaHCO 3 The aqueous solution was adjusted to pH 8. The ethyl acetate layer was extracted and washed 3 times with saturated NaCl aqueous solution, and then washed with 5% KHSO 4 The aqueous solution was extracted and washed once, and the ethyl acetate layer was left to stand, and a colorless solid was precipitated. After drying, it was recrystallized with metha...

Embodiment 3

[0033]Example 3 Preparation of 1-(4-isopropylphenyl)-β-carboline-3-carboxylic acid methyl ester (3)

[0034] Weigh 13.92g (40mmol) (3S)-1-(4-isopropylphenyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester and 5.772g (52mmol) Add selenium dioxide into a 250mL eggplant bottle, add 100mL dioxane to dissolve, place in an oil bath and heat to 75°C, react for 10h, and stop the reaction after TLC monitors that the raw material point disappears. The reactant was cooled to room temperature, filtered under reduced pressure, and the filtrate was concentrated to dryness under reduced pressure to obtain 12.384 g (95%) of the title compound as a yellow solid. ESI-MS(m / e): 345.2[M+H] + .

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Abstract

The invention discloses 1-(4-isopropylphenyl)-[beta]-carboline-3-formyl-Trp-Trp-Trp-Leu-Asp-Val, a preparation method, a nano structure and an anti-tumor effect of the compound, an effect of the compound of inhibiting adhesion, invasion and migration of tumor cells and an application of the compound in medicine.

Description

technical field [0001] The present invention relates to 1-(4-isopropylphenyl)-β-carboline-3-formyl-Trp-Trp-Trp-Leu-Asp-Val and a preparation method thereof, to its nanostructure, to its The anti-tumor effect in vivo and in vitro involves its anti-tumor cell adhesion, invasion and migration. Therefore, the present invention relates to its application in the preparation of anti-tumor drugs and anti-tumor cell adhesion, invasion and migration drugs. 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 th...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/06A61K38/08A61P35/00B82Y30/00
CPCY02P20/55
Inventor 赵明彭师奇王玉记吴建辉王程荣
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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