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Bufogenin derivative and preparation method thereof, composition containing bufogenin derivative and applications thereof

A technology of bufagenin and derivatives, which can be applied in drug combinations, pharmaceutical formulations, steroids, etc., and can solve problems such as insufficient patient selection and unsatisfactory pharmacological activity

Active Publication Date: 2012-07-04
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] However, the pharmacological activity of the above-mentioned compounds is still unsatisfactory, and the options provided to patients are still insufficient

Method used

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  • Bufogenin derivative and preparation method thereof, composition containing bufogenin derivative and applications thereof
  • Bufogenin derivative and preparation method thereof, composition containing bufogenin derivative and applications thereof
  • Bufogenin derivative and preparation method thereof, composition containing bufogenin derivative and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] The preparation of embodiment 1 compound II1B-01

[0109]

[0110] In a 50mL round-bottomed flask, dissolve p-nitrophenyl chloroformate (1.206g, 6mmol) in 10mL of anhydrous dichloromethane, add dry pyridine (0.67mL), a white precipitate appears immediately, and dropwise add A dichloromethane solution (10 mL) of bufalin (2 mmol) was stirred at room temperature for 6 hours, washed twice with water after the reaction was completed, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to silica gel column chromatography (90:10, Petroleum ether / acetone) to obtain intermediate A.

[0111] In a 10 mL round bottom flask, dissolve Intermediate A in 3 mL of dichloromethane, add triethylamine (35 μL), add N,N-dimethylethylenediamine (6 mmol), and stir at room temperature for 2 hours (following The reaction time of a similar reaction is determined by thin-layer chromatography detection), after the completion of the reaction, wash once with satur...

Embodiment 2

[0112] The preparation of embodiment 2 compound II1B-02

[0113]

[0114] The reaction operation is as in the preparation of compound II1B-01, the raw material is N, N-diethylethylenediamine instead of N, N-dimethylethylenediamine; silica gel column chromatography eluent: petroleum ether / acetone / ammonia water (50 :50:0.5), the yield was 78%. 1 H NMR (CDCl 3 , 300MHz) δ7.84(dd, 1H, J=9.6, 2.4Hz), 7.22(d, 1H, J=2.4Hz), 6.25(d, 1H, J=9.6Hz), 5.21(br s, 1H) , 3.23(d, 2H, J=5.4Hz), 2.55(m, 6H), 1.02(t, 6H, J=7.2Hz), 1.09-2.26(m, 22H), 0.94(s, 3H), 0.69( s, 3H); 13 C NMR (CDCl 3 , 75MHz) δ11.8, 11.8, 16.7, 21.5, 21.6, 23.9, 25.5, 26.6, 28.9, 29.9, 30.9, 32.9, 35.3, 36.0, 36.9, 38.7, 41.0, 42.5, 47.1, 47.1, 48.5, 51.4, 52.1 , 70.7, 85.5, 115.4, 122.9, 147.1, 148.7, 156.6, 162.6; ESI-MS (m / z) 529.5 [M+1] + .

Embodiment 3

[0115] The preparation of embodiment 3 compound II1B-03

[0116]

[0117] The reaction operation is as in the preparation of II1B-01, the raw material is N, N, N'-trimethylethylenediamine instead of N,N-dimethylethylenediamine; silica gel column chromatography eluent: petroleum ether / acetone / trimethylethylenediamine Ethylamine (60:40:0.5), 90% yield. 1 H NMR (CDCl 3 , 300MHz) δ7.83(dd, 1H, J=9.6, 2.4Hz), 7.22(d, 1H, J=2.4Hz), 6.24(d, 1H, J=9.6Hz), 4.99(brs, 1H), 3.36(t, 2H, J=7.2Hz), 3.36(s, 3H), 2.44(t, 2H, J=7.2Hz), 2.26(s, 6H), 1.20-2.20(m, 22H), 0.94(s , 3H), 0.69(s, 3H); 13 C NMR (CDCl 3 , 75MHz) δ16.7, 21.5, 21.6, 24.1, 25.5, 26.6, 28.9, 29.8, 30.9, 32.9, 34.6, 35.3, 36.0, 37.4, 41.0, 42.5, 47.1, 45.9, 48.5, 51.4, 57.0, 57.4, 71.2 , 85.4, 115.4, 122.9, 147.1, 148.7, 156.1, 162.6; ESI-MS (m / z) 515.3 [M+1] + .

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Abstract

The invention provides a bufogenin derivative of the following general formula I or a pharmaceutically-acceptable salt, a preparation method thereof, a pharmaceutical composition containing the derivative, and applications of the bufogenin derivative and the pharmaceutical composition. The bufogenin derivative has inhibitory activity on various human tumor cell lines and can be used as an anticancer drug against malignant tumors.

Description

[0001] Cross References to Related Applications [0002] This application claims the priority benefit of Invention Patent Application No. 201110180620.4 filed with the State Intellectual Property Office of China on June 30, 2011, the entire contents of which are hereby incorporated by reference in their entirety as if fully set forth herein. technical field [0003] The present invention relates to the field of medicinal chemistry, in particular, the present invention relates to a new class of bufotalins, a preparation method thereof, a pharmaceutical composition comprising the derivative, and an application thereof. The bufagenin derivative has inhibitory activity on tumor cell lines and can be used as a medicine for treating malignant tumors. Background technique [0004] Tumor is one of the malignant diseases that threaten human life. The number of deaths due to tumors in the world is more than 5 million every year. In China, there are more than 1.6 million new cancer pat...

Claims

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Application Information

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IPC IPC(8): C07J19/00C07J43/00A61K31/585A61P35/00
CPCC07J43/00C07J19/00A61P35/00C07J41/0005C07J41/0011C07J41/0027C07J41/0055C07J43/003
Inventor 胡立宏果德安肖志勇刘璇马彪雷敏
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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