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Quinoline compounds, synthesizing method, applications in synthesis of alkaloid of camptothecins

A technology of compounds and quinolines, which is applied in the field of organic synthesis, can solve problems such as not being practical and in great demand

Inactive Publication Date: 2009-01-07
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the amount of camptothecin obtained from natural materials such as camptothecin as raw materials is extremely small, and the demand for useful non-natural camptothecin derivatives is extremely large, and the method of realizing raw materials through plants is greatly limited.
In addition, when studying the preparation method of total synthesis, due to the problems of equipment, yield and cost, etc., it has not been practical yet.

Method used

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  • Quinoline compounds, synthesizing method, applications in synthesis of alkaloid of camptothecins
  • Quinoline compounds, synthesizing method, applications in synthesis of alkaloid of camptothecins
  • Quinoline compounds, synthesizing method, applications in synthesis of alkaloid of camptothecins

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]

[0051] In compound 5 (5g, 39mmol) dichloromethane solution, add molecular sieves, catalytic amount of pyrrolidine (0.32mL, 3.9mmol) and benzoic acid (0.32mL, 3.9mmol), after stirring for five minutes, add compound 4 (7.09g , 58.57mmol), stirred at room temperature for about half an hour. After the reaction was completed, the molecular sieves were filtered off, silica gel was added to the filtrate, and the mixture was stirred overnight at room temperature. Silica gel was filtered off, concentrated, and column chromatography gave product 6a (R 1 =H, 8.44 g, 82%).

[0052] 1 H NMR (CDCl3, 300MHz): δ9.52(s, 1H), 7.28(d, 1H, J=4.8Hz), 7.15(t, 1H, J=7.9Hz), 7.10(d, 1H, J=7.5 Hz), 6.67(t, 1H, J=7.4Hz), 6.52(d, 1H, J=8.1Hz), 4, 82(m, 1H), 4.67(s, 1H), 4.04(m, 2H), 1.94(s, 3H),

[0053] According to the same operation, compound 6b (R 1 =OMe, 84%).

[0054] 1 H NMR (CDCl3, 300MHz): δ9.53(s, 1H), 7.25(s, 1H), 6.81(dd, 1H, J=8.7, 3.0Hz), 6.66(d, 1H, J=3.3Hz), 6.50(d, ...

Embodiment 2

[0056]

[0057] At room temperature, the activated manganese dioxide (13.2g, 151.5mmol) was added to the dichloromethane solution of compound 6 (7.0g, 30.3mmol) at one time, and stirred at room temperature until the raw material disappeared. Filtration, concentration, column chromatography, product 7a (R 1 =H, 6.2 g, 89%).

[0058] 1 H NMR (300MHz, CDCl 3 ): δ10.31(s, 1H), 8.69(s, 1H), 8.16(d, 1H, J=8.7Hz), 8.00(d, 1H, J=7.8Hz), 7.90(m, 1H), 7.67 (m, 1H), 5.75(s, 2H), 4, 82(m, 1H), 2.24(s, 3H).

[0059] According to the same operation, compound 7b (R 1 =OMe, 87%).

[0060] 1 H NMR (300MHz, CDCl 3 ): δ10.31(s, 1H), 8.69(s, 1H), 8.45(d, 1H, J=9.3Hz), 7.52(dd, 1H, J=7.8, 2.7Hz), 7.22(d, 1H, J=2.1Hz), 5.70(s, 2H), 3.97(s, 3H), 2.20(s, 3H).

Embodiment 3

[0062]

[0063] Add hydroxylamine hydrochloride (2.54g, 36.5mmol) and sodium acetate (2.99g, 36.5mmol) successively to the ethanol solution of compound 7 (5.57g, 24.3mmol), and stir at room temperature for about ten minutes. After spinning off most of the ethanol, water was added, extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated, and directly put into the next step.

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Abstract

The invention relates to quinoline compound, a synthesis method and the application for preparing medicines of camptothecin alkaloid. The syntheticroute is concise, high-efficient and economical, and can play a great role in promoting the later industrialized production of camptothecin alkaloid.

Description

technical field [0001] This patent relates to the field of organic synthesis. More specifically, it relates to a class of quinoline compounds that are intermediates for the synthesis of camptothecin alkaloids. Differently substituted quinoline compounds can be synthesized from simple and easy-to-obtain raw materials and used as synthetic intermediates It is used in the synthesis of camptothecin alkaloid drugs. Background technique [0002] Quinolines are a major class of heterocyclic compounds, and many methods for their preparation have been developed since the late 19th century. Among them, the skeleton quinoline ring is commonly found in some natural products, drugs, and functional materials, especially in alkaloids. Therefore, the construction method of the quinoline ring is of great significance for the synthesis and design of many active molecules. [0003] A variety of natural products contain quinoline structures, and camptothecin alkaloids are one of them. Campto...

Claims

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Application Information

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IPC IPC(8): C07D215/20C07D215/12C07D471/04C07D491/22A61P35/00
Inventor 姚祝军刘观赛董情理姚元山
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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