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Bisbenzylisoquinoline betaine as well as preparation method thereof and application thereof in preparation of anti-tumor medicament

A technology of bisbenzylisoquinoline and betaine, which is applied in the direction of antineoplastic drugs, drug combinations, and pharmaceutical formulations, can solve problems such as unsatisfactory curative effects, and achieve the effects of strong activity, reduced toxicity, and high product purity

Active Publication Date: 2014-07-09
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, most of the drugs currently used clinically in my country for the treatment of liver cancer are unsatisfactory in efficacy. Therefore, it is very necessary to research and develop new anti-hepatic tumor drugs with better efficacy.

Method used

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  • Bisbenzylisoquinoline betaine as well as preparation method thereof and application thereof in preparation of anti-tumor medicament
  • Bisbenzylisoquinoline betaine as well as preparation method thereof and application thereof in preparation of anti-tumor medicament
  • Bisbenzylisoquinoline betaine as well as preparation method thereof and application thereof in preparation of anti-tumor medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Weigh 6.10g of 7-hydroxybisbenzylisoquinoline (in general formula III, X=OH), 3mL of methyl 2-chloroacetate and 1.50g of potassium carbonate, dissolve them in 200mL of ethanol, add them to a 500mL three-necked flask, heat and stir Bring to boil, keep warm and stir for 24 hours, distill ethanol out under reduced pressure, cool down to room temperature, add 50 mL of water, stir at 60 °C for 4 hours, neutralize to neutral with 10% hydrochloric acid, extract 3 times with chloroform (50 mL×3), trace with TLC The separation and purification process of the reaction and the product, the extract is anhydrous Na 2 SO 4 After drying for 8 hours, chloroform was recovered, and the solid was dried at 60°C for 4 hours to obtain 5.87 g of a light yellow powder product with a yield of 83.34% and a purity of 97.23%. The melting point of the target product: 147-148°C, 13 C NMR (75MHz, DMSO-d 6 ): δ20.65(C-4), 23.24(C-4’), 35.67(C-15), 49.70(C-15’), 50.69(NCH 3 ), 53.24 (N'CH 3 ), 53....

Embodiment 2

[0039] Weigh 6.10 g of 7-hydroxybisbenzylisoquinoline (in general formula III, X=OH) and 2.00 g of sodium tert-butoxide, add it to a 500 mL three-necked flask, dissolve it in 100 mL of DMSO, and then add 2-chlorobutyric acid in batches Ethyl ester 50mL, stirred and mixed evenly, stirred and reacted at room temperature for 48h, added water 50mL, stirred at 50°C for 4h, neutralized with dilute hydrochloric acid to neutrality, 200g 200 mesh silica gel column chromatography, washed with dichloromethane-methanol (10:1) Detachment, TLC traced the separation and purification process of the reaction and the product, collected and combined the product fractions, and evaporated the solvent at 60 °C with a rotary evaporator to obtain 4.15 g of a light yellow powder product with a yield of 56.66% and a purity of 95.50 %. The melting point of the target product: 139-141°C, ESI-MS: M / e (348.1706), molecular formula: C 41 h 47 o 8 N 2 Cl, 13 CNMR characterization, namely compound 6 in T...

Embodiment 3

[0041]Weigh 6.10g of 7-hydroxybisbenzylisoquinoline (in general formula III, X=OH), 5mL of methyl 2-chloropropionate and 1.50g of sodium carbonate, dissolve them in 200mL of propanol, add them to a 500mL three-necked flask, Heat and stir until boiling, and keep stirring to react for 12 hours. Evaporate the solvent under reduced pressure, cool down to room temperature, add 50 mL of water, stir at room temperature for 24 hours, neutralize to neutral with 10% hydrochloric acid, and extract 3 times with acetone (60 mL×3), TLC Track the separation and purification process of the reaction and the product, and use anhydrous Na for the extract 2 SO 4 After drying for 8 hours, acetone was recovered, and the solid was dried at 60°C for 4 hours to obtain 5.65 g of a light yellow powder product with a yield of 78.65% and a purity of 95.87%. The melting point of the target product: 145-146°C, 13 CNMR experiment, ESI-MS: M / e (341.1627), molecular formula C 40 h 45 o 8 N 2 Cl, namely c...

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Abstract

The invention discloses bisbenzylisoquinoline betaine with anti-tumor activity and a preparation method thereof. The compound has the following structural general formula shown in the specification. The preparation method comprises the steps of taking bisbenzylisoquinoline compounds as raw materials, dissolving into a certain solvent, adding a catalyst and a reactant Y, mixing, performing reaction for 0.1-72 hours at -20 DEG C to 300 DEG C, performing hydrolysis and neutralization reaction on the materials after reaction, and then separating and purifying to obtain an objective product. According to the preparation method disclosed by the invention, the prepared bisbenzylisoquinoline betaine has a relatively good inhibiting effect on proliferation of the human liver cancer cell strain HepG2 and leukemia K562 cells, and can be used for preparing anti-tumor medicaments.

Description

technical field [0001] The invention relates to a novel bisbenzylisoquinoline betaine, its preparation method and its application in the preparation of antitumor drugs. Background technique [0002] BisBenzylisoquinoline compounds (bisBenzylisoquinoline compounds) have anticancer, antibacterial, anti-inflammatory, antihypertensive, regulating muscle relaxation, immune function and many other effects, among which the more important natural bisBenzylisoquinoline compounds include powder Tetrandrine, fangchinoline, berbamine, stepherine, chrysanthemum, curine, etc., such as tetrandrine, also known as tetrandrine or tetrandrine, is mainly used clinically for rheumatic pain, joint Pain, neuralgia, also used for silicosis. Hanjisong (dimethyl iodide tetrandrine, the quaternary ammonium salt of tetrandrine) is a striated muscle relaxant, which can be used clinically to relax striated muscles during surgery. Experimental studies have proved that tetrandrine has certain effects on ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/18A61K31/4748A61P35/00A61P35/02
CPCC07D491/18
Inventor 刘玉法顾巧莲刘海征张萌吴国梁
Owner SHANDONG NORMAL UNIV
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