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Production method of 9-nitro camptothecin

A technology of nitrocamptothecin and its production method, which is applied in the production field of 9-nitrocamptothecin to achieve the effect of improving product yield

Inactive Publication Date: 2007-08-29
王洋 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But, when using this method, the yield of 9-nitrocamptothecin product is only about 3~7%, and the unwanted by-product---12-nitrocamptothecin and 9-nitrocamptothecin that this method produces The ratio of alkali is about 3:1

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Dissolve 40g camptothecin in 1000mL acetic acid, add 200mL 30% hydrogen peroxide, react at 50°C for 5 hours, pour into 5000mL ice water, extract with dichloromethane, concentrate, and dissolve the residue in 1000mL concentrated In sulfuric acid, 80 mL of fuming nitric acid was added dropwise in an ice-water bath, and reacted at 50°C for 24 hours, then poured into 5000 mL of ice water, extracted with dichloromethane, concentrated to precipitate 9-nitro-N-camptothecin oxide crystals. The obtained 9-nitro-N-oxycamptothecin was dissolved in dioxane, refluxed for 48 hours, concentrated to obtain 9-nitrocamptothecin crude product, and the crude product was recrystallized from ethanol to obtain pure 9-nitrocamptothecin Taste.

Embodiment 2

[0023] Dissolve 40g camptothecin in 1000mL acetic acid, add 400mL 30% hydrogen peroxide, react at 80°C for 3 hours, pour into 5000mL ice water, extract with dichloromethane, concentrate, and dissolve the residue in 2000mL acetic acid After adding 200mL of sulfuric acid dropwise in an ice-water bath, add 60g of ferric nitrate to react for 72 hours at 30°C, then pour into 5000mL of ice water, extract with dichloromethane, concentrate and separate out 9-nitro-N-camptothecin oxide crystallization. The obtained 9-nitro-N-camptothecin oxide was dissolved in dioxane, refluxed for 72 hours, concentrated to obtain crude 9-nitrocamptothecin, and the crude product was recrystallized from acetone to obtain pure 9-nitrocamptothecin. Taste.

Embodiment 3

[0025] Dissolve 40g of camptothecin in 1000mL of acetic acid, add 400mL of 30% hydrogen peroxide, react at 30°C for 8 hours, pour into 5000mL of ice water, extract and concentrate with dichloromethane, and dissolve the residue in 1000mL of three In fluoroacetic acid, add 200mL of concentrated sulfuric acid dropwise in an ice-water bath, then add 70g of magnesium nitrate at 70°C to react for 48 hours, then pour it into 5000mL of ice water, extract with dichloromethane, concentrate and precipitate 9-nitro-N-oxidized camptothecin crystals . The obtained 9-nitro-N-oxycamptothecin was dissolved in dioxane, refluxed for 24 hours, concentrated to obtain 9-nitrocamptothecin crude product, and the crude product was recrystallized from acetic acid to obtain pure 9-nitrocamptothecin Taste.

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PUM

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Abstract

The invention provides a process for preparing 9-nitrocamptothecine which consists of the following steps, oxidizing camptothecine raw material to obtain N-oxidized camptothecine, nitrating the N-oxidized camptothecine, -dioxyhexacyclic inversing flow and concentrating to obtain 9-nitro camptothecine crude product, finally carrying out recrystallization to obtain the refined product, the final yield of the 9-nitrocamptothecine can reach over 50%, the product purity can reach over 97%.

Description

technical field [0001] The present invention and the semi-synthetic production method of the natural compound particularly relate to a production method of 9-nitrocamptothecin. Background technique [0002] Camptotheca acuminate Decaisne is a plant of the genus Camptotheca (Camptotheca) of the blue fruit tree family (also known as Davidiaceae, Nyssaceae). It is a unique subtropical tree species in my country. It likes a warm and humid climate. . [0003] Camptothecin (CPT) is an alkaloid isolated from camptothecin that has obvious inhibitory effects on a variety of tumor cells, and has a unique anticancer mechanism (camptothecin is the most important topological drug discovered so far. isomerase I inhibitor). 9-Nitrocamptothecin is a semi-synthetic derivative of camptothecin that has shown promise in the treatment of certain types of cancer. [0004] Japanese Published Patent Application No. 59-51288 provides a method for preparing 9-nitrocamptothecin by treating camptothe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/22C07D221/00C07D209/00C07D311/00
Inventor 王洋于涛阎秀峰
Owner 王洋
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