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Method for synthesizing 9-nitrocamptothecin
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A technology of nitrocamptothecin and nitrobenzene, applied in the direction of organic chemistry, etc., to achieve the effects of small waste discharge, high optical purity, and easy separation
Active Publication Date: 2013-08-21
HENAN DONGTAI PHARM
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And camptothecin is extracted from camptothecin. With the increasing depletion of camptothecin resources, the output of camptothecin can no longer meet the needs
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Embodiment 1
[0028] Embodiment 1: Preparation of 2,6-dinitrobenzaldehyde ethylene glycol acetal
[0029] Take 2,6-dinitrobenzaldehyde (5g, 0.026mol), 20ml of ethylene glycol, and 0.15g of p-toluenesulfonic acid dissolved in 250ml of toluene, dehydrate under reflux for 5h, evaporate to dryness, add 50ml of dichloromethane and 100ml of water, Separate layers, dichloromethane layer, dry over anhydrous sodium sulfate, concentrate to dryness to obtain the product, recrystallize from methanol to obtain 5.4g, yield 88.2%, Mp (melting point) 107-109°C.
Embodiment 2
[0030] Embodiment 2: Preparation of 2-amino-6-nitrobenzaldehyde ethylene glycol acetal
[0031] Take 2,6-dinitrobenzaldehyde ethylene glycol acetal (5g, 0.02mol), sodium sulfide (10g, 0.13mol) and dissolve it in 200ml of ethanol and 50ml of water, reflux for 30min, evaporate the ethanol under reduced pressure, add dichloro Extracted with 100ml of methane, dried over anhydrous sodium sulfate, evaporated to dryness to obtain a yellow solid, recrystallized from methanol to obtain 3.9g, yield 89.1%, Mp103~105℃.
[0033] Take 2-amino-6-nitrobenzaldehyde ethylene glycol acetal (2.1g, 0.01mol) and α-(S)-tricyclic amide (3.4g, 0.008mol) in a mixed solvent of ethanol and dichloromethane Add 0.1 g of concentrated hydrochloric acid, react at 80°C for 8 hours, cool, and filter to obtain crude 9-nitrocamptothecin, which is recrystallized in ethanol to obtain 3.1 g of 9-nitrocamptothecin with a yield of 78.9%. The experimental data are as follows:
[0034] C 20 h 15 N 3 o 6 , Mp 182~186℃, ee>99% (HPLC detection conditions: chiral column OD-H; mobile phase n-hexane / isopropanol / diethylamine=6 / 4 / 0.1; flow rate 0.5ml / min; detection wavelength 254nm).
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Abstract
The invention relates to a method for synthesizing 9-nitrocamptothecin. The method solves the technical problem that the 9-nitrocamptothecin cannot be industrially synthesized. The method comprises the following steps of: performing single nitro reduction on 2,6-dinitrobenzaldehyde serving as a raw material to obtain 2-amino-6-nitrobenzaldehyde glycol acetal, and performing condensation reaction on the2-amino-6-nitrobenzaldehyde glycol acetal and alpha-(S)-tricyclic amide to obtain the 9-nitrocamptothecin. The method has the advantages of mild reaction condition, simplicity and convenience inoperation, low cost, high product yield and good product purity, overcomes the defects of the prior art, and is suitable for industrialized batch synthesis production.
Description
technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a synthesis and preparation method of 9-nitrocamptothecin. Background technique [0002] Camptotheca acuminate Decaisne is a plant of the genus Camptotheca in the Davidiaceae family. It is a subtropical tree species unique to my country. It likes a warm and humid climate. It is widely distributed in the Yangtze River Basin and its southern provinces. Camptothecin (CPT) is a kind of alkaloid isolated from camptothecin, which has obvious inhibitory effect on many tumor cells, and has a unique anti-cancer mechanism. It is a topoisomerase I inhibitor. 9-Nitrocamptothecin, a derivative of camptothecin, has shown promise in the treatment of certain types of cancer. [0003] J.Med.Chem.1986,29,2358-2363 And Japanese published patent 59-51288 provides a kind of semi-synthetic method of camptothecin, adopts mixed acid nitration, yield only has 3~7%, and pollution is serious,...
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