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RGDS modified indoloquinolizine, preparation therefor, nanostructure, activity and application thereof

A technology of quinazine and tetrahydroindole, applied in RGDS, it has the effect of anti-tumor cell adhesion, invasion and migration, in the field of preparation of anti-tumor drugs, and can solve the problem of not getting anti-tumor and anti-tumor metastatic compounds and the like

Inactive Publication Date: 2016-01-06
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the inventor has spent a lot of research effort and screened hundreds of compounds, no compound with both anti-tumor and anti-metastasis effects has been obtained

Method used

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  • RGDS modified indoloquinolizine, preparation therefor, nanostructure, activity and application thereof
  • RGDS modified indoloquinolizine, preparation therefor, nanostructure, activity and application thereof
  • RGDS modified indoloquinolizine, preparation therefor, nanostructure, activity and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1 prepares L-tryptophan benzyl phosphate (1)

[0027] Add 20.4g (100mmol) of L-tryptophan, 120mmol of benzyl alcohol and 120mmol of polyphosphoric acid into a 500ml eggplant bottle in turn, install a condenser at the mouth of the bottle, place in an oil bath and heat to 80°C, react for 72 hours, TLC shows that the raw material Completely disappear, the reaction is over. The reaction solution was cooled to room temperature, and 30 ml of anhydrous ether was added to precipitate a white solid, which was stirred for 2 hours. The reaction solution was filtered under reduced pressure to obtain a white solid, which was washed three times with anhydrous ether to obtain 35.4 g (90.4%) of the target compound. It is a white solid. ESI-MS(m / e): 393.1[M+H] + .

Embodiment 2

[0028] Example 2 Preparation of (3S)-1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (2)

[0029] 250ml CH 2 Cl 2 Add it to a 500ml eggplant bottle, add 15ml 1,1,3,3-tetramethoxypropane and 14ml trifluoroacetic acid successively under ice bath, stir for 0.5 hours, add 20.0g (68mmol) L-tryptophan benzyl ester, stir at room temperature After 120 hours, the reaction ended. Slowly add saturated Na to the reaction solution with stirring in an ice bath 2 CO 3 aqueous solution, stirred vigorously until the pH of the aqueous layer was 7, separated the dichloromethane layer, and washed the dichloromethane layer with 5% NaHCO 3 aqueous solution and saturated NaCl aqueous solution were extracted and washed 3 times, and the dichloromethane layer was washed with anhydrous NaCl 2 SO 4Dry, filter under reduced pressure, and concentrate the filtrate to dryness under reduced pressure. The residue is purified by silica gel column chromatography (petrol...

Embodiment 3

[0030] Example 3 Preparation of (3S)-1-(2,2-dimethoxyethyl)-2-acetoacetyl-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (3)

[0031] Dissolve 9.38g (23.8mmol) (3S)-1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-β-carboline-3-carboxylic acid benzyl ester in 200ml Acetone, 2.89ml of diketene and 1.81ml of triethylamine were added under stirring in an ice bath, and stirred at room temperature for 18 hours. TLC showed that the raw materials completely disappeared, and the reaction was completed. Add 10ml of distilled water under stirring in an ice bath, stir for 1 hour, concentrate under reduced pressure to remove acetone, extract the residue 3 times with dichloromethane, combine the dichloromethane layers, and successively wash with 5% NaHCO 3 aqueous solution and saturated NaCl aqueous solution were extracted and washed 3 times, and the dichloromethane layer was washed with anhydrous NaCl 2 SO 4 After drying and filtering under reduced pressure, the filtrate was co...

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Abstract

The invention discloses (6S)-3-acetyl-4-oxo-4,6,7,12-tetrahydroindole [2,3-a] quinolizine-6-formyl-Arg-Gly-Asp-Ser structured as follows, wherein the standard abbreviation of Arg-Gly-Asp-Ser is RGDS. The invention discloses a preparation method therefor, a nanostructure thereof, antitumor action thereof and action thereof in resisting adhesion, invasion and migration of tumor cells, and illustrates application thereof in medical science. The formula is shown in t he description.

Description

technical field [0001] The present invention relates to (6S)-3-acetyl-4-oxo-4,6,7,12-tetrahydroindolo[2,3-a]quinazine-6-formyl-Arg-Gly-Asp- The formal abbreviation of Ser, Arg-Gly-Asp-Ser is RGDS. It relates to its preparation method, its nanostructure, its in vivo and in vitro anti-tumor effects, and its anti-tumor cell adhesion, invasion, and migration effects. 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 tumo...

Claims

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Application Information

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IPC IPC(8): C07K7/06A61K38/08A61P35/00A61P35/04B82Y30/00
Inventor 彭师奇赵明王玉记吴建辉周倩羽
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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