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Chemical synthesis method of Epothilone B-lactam derivative

A technology of epothilone and synthesis method, which is applied in drug combination, organic chemistry, antineoplastic drugs, etc., can solve the problem of no chemical synthesis of epothilone B-lactam derivatives, etc., and achieve strong anticancer activity, The preparation process is simple and the effect of cost saving

Inactive Publication Date: 2010-11-10
泰州市宝嵘新材料有限公司
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Problems solved by technology

However, there is no method for the chemical synthesis of epothilone B-lactam derivatives

Method used

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Embodiment Construction

[0007] The invention provides a chemical synthetic method of epothilone B-lactam derivatives, which comprises the following steps: Step 1, ring-opening nitriding reaction: under nitrogen protection, drop into 800ml mixed solution (tetrahydrofuran: Water=9:1), epothilone B25g (5.76mmol) and 3.5g (0.35mmol) tetrakis (triphenylphosphine) palladium, drop into 4.76g (8.64mmol) sodium azide in batches, under stirring, Slowly raise the temperature to 60°C, stir for 7 hours, track TLC:EtOAc / MSO=1:2 during the stirring process, so that the reaction state is that the solution turns yellow, and then extract with ethyl acetate, and the ethyl acetate is divided into 3 times , each time 250ml is extracted, the organic phase is washed with saturated brine, and the washing is carried out twice, and each time 200ml of the organic phase is used to wash with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain 17.1g of nitric acid; step 2, Hydrolysis reaction...

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Abstract

The invention discloses a synthesis method of Epothilone B-lactam derivative, which comprises the following steps that: Epothilone B and sodium azide are adopted as initial raw materials, catalyst is selected, open-loop diazo-reaction is proceeded to generate nitronic acid, then hydrolysis reaction is proceeded to generate amino acid, and ring-closure reaction is proceeded to generate Epothilone B-lactam derivative. The chemical synthesis method can effectively and chemically synthesize Epothilone B-lactam derivative.

Description

technical field [0001] The invention relates to a chemical synthesis method of epothilone B-lactam derivatives. Background technique [0002] Epothilone (epothilone) is a class of macrolide compounds, first reported in 1993 by G. Hö, fle et al. of the German National Center for Biotechnology (GBF). Epothilone can be isolated from the fermentation liquid of the Myxobacteria suborder S. cellulosus strain, and its main components are Epothilone A and B. In 1995, D.M.Bollag of Merck Research Institute et al. screened microtubule inhibitors on a large scale It was found that a fermented extract of S. cellulosus SMP 44 had the activity of inhibiting microtubule depolymerization, and the active components were identified as epothilone (epothilone) A and B, which have the same inhibitory effect on tumor cells as paclitaxel. The mechanism of action of growth, and showed strong anticancer activity against multidrug-resistant tumor cells and paclitaxel-resistant tumor cells. However,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/044A61P35/00
Inventor 高荣周彬
Owner 泰州市宝嵘新材料有限公司
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