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Paclitaxel derivatives and preparation method thereof

A drug and compound technology, applied in the field of paclitaxel derivatives and its preparation, can solve the problems of cardiovascular toxicity, poor water solubility, neurotoxicity, etc., and achieve good anticancer effect and good anticancer activity

Inactive Publication Date: 2014-10-08
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because paclitaxel has adverse reactions such as allergic reactions, poor water solubility, neurotoxicity, and cardiovascular toxicity

Method used

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  • Paclitaxel derivatives and preparation method thereof
  • Paclitaxel derivatives and preparation method thereof
  • Paclitaxel derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of Example 1 Compound 56

[0042] Under argon protection, TrocCl (2.49ml, 18.18mmol) was added dropwise to a solution of compound 55 (3g, 5.51mmol) in pyridine (54ml) at 0°C, and reacted at room temperature for 1h. TLC detected that the reaction was complete, and pyridine was removed under reduced pressure. Add 80ml ethyl acetate, 50ml water, extract with ethyl acetate (50ml×2), wash with saturated sodium chloride (50ml), dry over anhydrous sodium sulfate, concentrate, column chromatography (PE:EA=3:1) Compound 56 (3.96 g, 81%) was obtained as a white solid.

Embodiment 2

[0043] Synthesis of Example 2 Compound 58

[0044] Add compound 56 (3g, 3.36mmol), compound 57 (3.24g), DCC, and DMAP to the reaction flask in sequence, add 68mL of toluene under the protection of argon, stir and react at 85°C for 2h, after HPLC monitoring the reaction is complete, remove the toluene under reduced pressure , add 80ml of ethyl acetate, 50ml of water, stir for 20min, filter to remove insoluble matter, extract with ethyl acetate (50ml×2), wash with saturated sodium chloride (50ml), dry over anhydrous sodium sulfate, concentrate, column chromatography (PE:EA=3:1) yielded compound 58 (3.70 g, 92%).

Embodiment 3

[0045]Synthesis of Example 3 Compound 59

[0046] Add zinc powder (6.75g, 92.87mmol) and acetic acid to the methanol (120ml) solution of compound 58 (3.7g, 3.09mmol) successively, after reacting at 30 ℃ for 5h, TLC detects that the reaction is complete, the zinc powder is removed by filtration, and the methanol is removed under reduced pressure and acetic acid, add 100ml ethyl acetate, 50ml water, extract with ethyl acetate (50ml×2), wash with saturated sodium chloride (50ml), dry over anhydrous sodium sulfate, concentrate, column chromatography (PE:EA=3 : 1) Compound 59 (2.53 g, 90%) was obtained as a white solid.

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Abstract

The invention provides paclitaxel derivatives with a general structural formula (I) as described in the invention. The invention further provides application of the paclitaxel derivatives in preparation of drugs used for preventing or treating fibrosarcoma, liver cancer, lung cancer, leukemia, epidermoid carcinoma, breast cancer, prostatic cancer, lymphoma, stomach cancer, myeloma and pancreatic cancer. The derivatives synthesized in the invention have better water-solubility compared with paclitaxel and are superior to paclitaxel in the aspect of a plurality of anticancer effects.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a paclitaxel derivative and a preparation method thereof. Background technique [0002] Paclitaxel is a new type of broad-spectrum anti-tumor drug, which has a significant effect in the treatment of advanced ovarian cancer, breast cancer, non-small cell lung cancer and other malignant tumors. However, its poor water solubility, poor selectivity, and large toxic and side effects have greatly affected its curative effect and safety. The new paclitaxel derivatives we synthesized overcome these shortcomings to a certain extent, and also have good biological activity. [0003] The structure of paclitaxel: [0004] [0005] Malignant tumor is one of the main diseases that seriously affect human health and threaten human life. Together with cardiovascular and cerebrovascular diseases and accidents, cancer constitutes the top three causes of death in all countries in the world to...

Claims

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Application Information

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IPC IPC(8): C07D305/14A61K31/337A61P35/00A61P35/02
CPCC07D305/14
Inventor 姚志艺蒋晟李彩红王东升
Owner SHANGHAI INST OF TECH
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