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Water-soluble paclitaxel ester compounds containing 1,2,3-triazole and preparation method

A technology of paclitaxel esters and compounds, applied in medical preparations containing active ingredients, organic chemistry, drug combinations, etc., can solve the problems of complex separation, easy precipitation, and reduced product yield, so as to simplify the synthesis steps and increase water solubility , the effect of easy access to raw materials

Active Publication Date: 2011-04-06
SHANGHAI TIANCI INT PHARMA
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Problems solved by technology

[0005] However, there are still many problems: most of the reported water-soluble paclitaxel have low solubility, some are unstable and easy to precipitate, and the derivatization synthesis is difficult. The introduction of water-soluble groups is often accompanied by the occurrence of side reactions, which reduces the product yield and complicates the separation. , especially the existing methods are difficult to simultaneously introduce multiple water-soluble groups and synthesize serialized water-soluble paclitaxel

Method used

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  • Water-soluble paclitaxel ester compounds containing 1,2,3-triazole and preparation method
  • Water-soluble paclitaxel ester compounds containing 1,2,3-triazole and preparation method
  • Water-soluble paclitaxel ester compounds containing 1,2,3-triazole and preparation method

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Embodiment Construction

[0041] The following examples are used to further illustrate the present invention, but this does not imply any limitation to the present invention.

[0042] A) Synthesis of alkyne-containing paclitaxel 2

[0043] Such as image 3 As seen in the reaction formula, paclitaxel 1 (0.03mmol, 25.6mg) (Aladdin's reagent, 99%) was added to a dry reaction bottle, and dissolved in 3mL of benzene. Add p-carboxyphenylacetylene (0.03 mmol, 4.4 mg) and 4-dimethylaminopyridine DMAP (0.04 mmol, 5 mg) to the reaction solution, and stir at room temperature for 15 minutes. Then N, N-dicyclohexylcarbodiimide DCC (0.15 mmol, 31 mg) was added, the reaction was continued to stir at room temperature for 21 hours, and then the reaction was terminated. The solvent was evaporated under reduced pressure, and then separated by column chromatography (eluent: ethyl acetate / n-hexane = 1:2) to obtain a white powdery substance, of which 8% was C-7 substituted acetylene benzoate paclitaxel, and the rest It i...

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Abstract

The invention relates to a water-soluble paclitaxel ester containing 1, 2, 3-triazole, and a preparation method thereof, which takes paclitaxel as the raw material to carry out esterification reaction with 4-alkynyl benzoic acid under the existence of the dehydrating agent, dicyclohexylcarbodiimide (DCC) and 4-dimethylamino pyridine (DMAP), so as to synthetize the paclitaxel molecule containing alkynyl, and then carries out 1, 3-dipolar cycloaddition reaction with water-soluble azido-acetic acid or 4-azido-benzoic acid under the existence of the catalyst, Cu(I), and sodium ascorbate, thus quickly, simply and conveniently synthetizing the water-soluble paclitaxel containing carboxylic group. Compared with the existing paclitaxel, the water-soluble paclitaxel which is synthetized by the invention and contains water-soluble carboxylic group and polarity 1, 2, 3-triazole heterocycle improves the water-solubility and can be used for curing various cancers. The invention has the advantages of mild reaction condition in the method for preparing the water-soluble paclitaxel, easy post treatment, high yield and being suitable for industrial production.

Description

technical field [0001] The invention relates to a water-soluble taxol ester compound containing 1,2,3-triazole and a preparation method thereof. The compound can be used for treating various cancers. Background technique [0002] Paclitaxel is a natural organic compound extracted from yew leaves, bark, branches and other parts. It has broad-spectrum anti-cancer properties and has a strong killing effect on tumor cells such as uterine cancer, breast cancer, lung cancer and leukemia. [1] . Due to the special curative effect of paclitaxel, it is listed as the first choice anti-cancer drug by the United States and other developed countries. According to the statistics of the United States in 2006, the total sales of paclitaxel preparations in the international market, including paclitaxel injections processed from natural raw materials and semi-synthetic paclitaxel injections, have reached 3.7 billion US dollars, ranking first in the world's anticancer drugs. Dr. Samuel Broder...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12A61K31/4192A61P35/00C07D305/14A61K31/337
Inventor 匡春香胡婷华傅大煦
Owner SHANGHAI TIANCI INT PHARMA
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