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Theanine-modified carboline acyl amino acid benzyl ester, as well as preparation, anti-tumor activity and application thereof

An anti-tumor agent, carboline technology, applied in the fields of anti-tumor activity and clinical application prospects of anti-tumor drugs, can solve the problems of high toxicity and unsatisfactory curative effect of anti-tumor drugs

Inactive Publication Date: 2013-12-18
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the limitations of unsatisfactory curative effect and high toxicity in most of the clinically used anti-tumor drugs, finding new anti-tumor drugs has always been one of the hot spots of new drug research.

Method used

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  • Theanine-modified carboline acyl amino acid benzyl ester, as well as preparation, anti-tumor activity and application thereof
  • Theanine-modified carboline acyl amino acid benzyl ester, as well as preparation, anti-tumor activity and application thereof
  • Theanine-modified carboline acyl amino acid benzyl ester, as well as preparation, anti-tumor activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1 prepares 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1)

[0014] Put 200mL of water in a 250mL round bottom flask, and slowly add 0.1mL of concentrated sulfuric acid. 2.52 g (12.4 mmol) of L-tryptophan was added to the obtained dilute sulfuric acid solution and ultrasonically oscillated until the L-tryptophan was completely dissolved. To the resulting solution was added 5 mL of 37-40% formaldehyde solution. The reaction mixture was stirred at room temperature for 6 hours. The disappearance of L-tryptophan was detected by thin layer chromatography, and the reaction was terminated. The pH of the reaction solution was adjusted to 6 by slowly adding concentrated ammonia water dropwise, and left to stand for half an hour. The resulting precipitate filtered out under reduced pressure was repeatedly rinsed with water and acetone 3 times, and the filtered colorless solid was spread on a petri dish, placed in a fume hood and dried to obtain 2.64 g (98%) o...

Embodiment 2

[0015] Embodiment 2 prepares 3S-N-Boc-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2)

[0016] Add 20mL DMF to a 100mL eggplant bottle, and add 2.033g (9.41mmol) 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1) under stirring to obtain a white turbid suspension. Add 2.752 g (12.6 mmol) of di-tert-butyl dicarbonate (Boc 2 O), then add triethylamine to adjust the pH value to 10. The reaction mixture was stirred at room temperature for 48 hours, monitored by TLC until 1 disappeared, and the reaction was terminated. The reaction solution was concentrated to dryness under reduced pressure. The resulting oil was dissolved in 100 mL of ethyl acetate and then washed with KHSO 4 Aqueous solution (5%) washed (10 mL×3). The combined ethyl acetate layers were separated, dried by adding anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure, and a colorless solid was precipitated. The resulting colorless solid was suspended ...

Embodiment 3

[0017] Example 3 Preparation of 3S-N-Boc-1,2,3,4-tetrahydro-β-carboline-3-formyl-theanine benzyl ester (3)

[0018] Add 2.084g (6.59mmol) 3S-N-Boc-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2) to 250mL eggplant bottle under ice bath, 1.651g (5.50mmol ) HCl·Theanine-OBzl, 0.758g (6.59mmol) N-hydroxybenzotriazole (HOBt) and 50mL anhydrous tetrahydrofuran (THF), stirring and dissolving to obtain reaction solution I. 1.358 g (6.59 mmol) of dicyclohexylcarbonyldiimide (DCC) was dissolved in 10 mL of anhydrous THF to obtain reaction solution II. The reaction solution II was slowly added dropwise to the reaction solution I under an ice bath, stirred thoroughly for 5 minutes, and the pH was adjusted to 8 with N-methylmorpholine (NMM). The reaction mixture was stirred at 0°C for 6 hours, and dicyclohexylurea (DCU) was filtered off, and the filtrate was concentrated to dryness under reduced pressure. The obtained residue was dissolved in 150 mL of ethyl acetate and washed succe...

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Abstract

The invention relates to theanine-modified carboline acyl amino acid benzyl ester, as well as preparation, anti-tumor activity and application thereof, discloses 17 compounds represented by a general formula I (in the formula, AA is selected from L-Leu, L-Glu, L- Val, L-Trp, L-Pro, L-Tyr, L-Met, L-Phe, L-Ala, L-Gly, L-Asn, L-Asp, L-Ile, L-Lys, L-Ser and L-Theanine residues, or AA-OBzl jointly represents OBzl), and discloses preparation and synthesis methods thereof. The invention further discloses in-vivo and in-vitro anti-tumor activity thereof and clinical application prospects thereof as anti-tumor medicaments.

Description

field of invention [0001] The present invention relates to 17 compounds represented by general formula I (in the formula, AA is selected from L-Leu, L-Glu, L-Val, L-Trp, L-Pro, L-Tyr, L-Met, L-Phe, L -Ala, L-Gly, L-Asn, L-Asp, L-Ile, L-Lys, L-Ser, L-Theanine residues, or AA-OBzl collectively represent OBzl), related to their preparation and synthesis methods, further Involving their anti-tumor activity in vivo and in vitro, thus the present invention relates to their clinical application prospects as anti-tumor drugs. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Malignant tumor is a common and frequently-occurring disease that seriously threatens human health. In the past 20 years, the mortality rate of cancer in my country has increased by 29.42%. Among middle-aged and middle-aged people aged 35 to 59, tumors have ranked first among various causes of death. Statistics show that the incidence of cancer in my country is about...

Claims

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Application Information

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IPC IPC(8): C07D471/14A61K31/437A61P35/00
Inventor 赵明彭师奇王玉记吴建辉崔莹
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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