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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: 2006-01-25
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 40 g of camptothecin in 1000 mL of acetic acid, add 200 mL of 30% hydrogen peroxide, react at 50°C for 5 hours, pour into 5000 mL of ice water, extract with dichloromethane, concentrate, and dissolve the residue in 1000 mL of concentrated In sulfuric acid, 80 mL of fuming nitric acid was added dropwise to an ice-water bath, reacted at 50° C. for 24 hours, then poured into 5000 mL of ice-water, extracted with dichloromethane, and concentrated to precipitate 9-nitro-N-camptothecin crystals. The obtained 9-nitro-N-camptothecin oxide was dissolved in dioxane, refluxed for 48 hours, concentrated to obtain a crude 9-nitrocamptothecin, and the crude product was recrystallized from ethanol to obtain pure 9-nitrocamptothecin. Taste.

Embodiment 2

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

Embodiment 3

[0025] Dissolve 40 g of camptothecin in 1000 mL of acetic acid, add 400 mL of 30% hydrogen peroxide, react at 30 °C for 8 hours, pour into 5000 mL of ice water, extract with dichloromethane, concentrate, and dissolve the residue in 1000 mL of trisodium chloride. In fluoroacetic acid, 200 mL of concentrated sulfuric acid was added dropwise to an ice-water bath, 70 g of magnesium nitrate was added at 70°C for 48 hours, and then poured into 5000 mL of ice water, extracted with dichloromethane, and concentrated to precipitate 9-nitro-N-camptothecin crystallization. . The obtained 9-nitro-N-camptothecin oxide was dissolved in dioxane, refluxed for 24 hours, concentrated to obtain a crude 9-nitrocamptothecin, 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 invention relates to a semi-synthetic production method of natural compounds, in particular to a production method of 9-nitrocamptothecin. Background technique [0002] Camptotheca acuminata Decaisne (Camptotheca acuminata Decaisne) is a plant of the genus Camptotheca (Camptotheca, also known as Dovetaceae, Nyssaceae). . [0003] Camptothecin (CPT) is an alkaloid isolated from Camptothecus that has obvious inhibitory effect on a variety of tumor cells, and has a unique anti-cancer mechanism (CPT is the most important topology discovered so far. Isomerase I inhibitor). 9-Nitrocamptothecin, a semi-synthetic derivative of camptothecin, has shown promising applications 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 camptothecin in concentrated sulfuric acid with a slight excess of concentrated nitric acid. However, when using th...

Claims

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Application Information

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