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Synthesis of anti-hepatitis B medicine LQC-X and application thereof

A technology of LQC-X1 and reaction, which is applied in the fields of chemistry and biological sciences, and can solve problems such as high price, virus rebound, and large side effects

Active Publication Date: 2012-09-19
北京鸿测科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Hepatitis B virus (Hepatitis B virus, HBV) and the resulting liver cirrhosis and liver cancer are one of the major diseases that threaten human life and health. At present, there is no effective treatment. In addition to vaccines, interferon, Lamy Fudin and others are widely used in clinical practice, but are greatly restricted due to their large side effects, high price, and viral rebound. Therefore, finding anti-hepatitis B virus drugs has always been a major issue for biologists and chemists.

Method used

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  • Synthesis of anti-hepatitis B medicine LQC-X and application thereof
  • Synthesis of anti-hepatitis B medicine LQC-X and application thereof
  • Synthesis of anti-hepatitis B medicine LQC-X and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1L

[0039] Synthesis of Preparation Example 1LQC-X1

[0040] Put 9.12g (0.02mol) of oleanolic acid, 400ml carbon tetrachloride, and 4.27g N-bromosuccinimide (about 0.024mol) in a 500ml reaction bottle, light, magnetically stir and heat to reflux at 74°C for 4 Hours, reacted to no raw material, and the reaction ended. Recover the reaction solution to dryness, dissolve the recovered solid with 200ml of ethyl acetate, filter it while it is hot, and place it at room temperature for 24 hours to crystallize to obtain a large amount of coarse crystals, recrystallize once with ethyl acetate to obtain LQC-X1, white flakes 7.13 g of crystals were obtained, and the reaction yield was 78.5%. m.p.276.7-278.4°C.

[0041] LQC-X1 related spectral data:

[0042] ESI-MS: [M-1] - 453

[0043] 1 H-NMR (500MHZ, CDCl 3 ): 083, 0.93, 0.97, 1.00, 1.05, 1.06, 1.20 (3H, each, s, 7×CH 3 ) 2.99 (m, 1H, 3-OH), 3.28 (m, 1H, H-3), 5.58 (d, 1H, J=5.5HZ, H-12), 5.62 (d, 1H, J=5.5HZ, H-11).1.000~2.500 (24...

preparation Embodiment 2L

[0045]Synthesis of Preparation Example 2LQC-X2

[0046] Weigh about 4.54g (0.01mol) of LQC-X1, dissolve it in 500ml of dichloromethane, add 200mg of Eosiy (alcohol solution), ventilate, and react with light for 10h. After the reaction, wash twice with 3 times the amount of saturated sodium bicarbonate solution, wash with water until neutral, remove water with anhydrous sodium sulfate, recover dichloromethane, pass through a silica gel column, and elute with petroleum ether: ethyl acetate = 5:1 . LQC-X2 was obtained, 2.05 g in total, and the reaction yield was 42.0%.

[0047] LQC-X2 related spectral data:

[0048] ESI-MS[M-1] - 487

[0049] 1 H-NMR (500MHZ, CDCl 3 ): 0.86, 0.98, 0.99, 1.02, 1.08, 1.28, 1.27 (3H, each, s, 7×CH 3 ), 3.01 (1H, m, H-3), 3.25 (1H, m, 3-OH), 6.02 (1H, s, H-12), 1.000~2.500 (24H, methylene in the three-layer core structure base and methine hydrogen signals);

[0050] 13 C-NMR (500MHZ, CDCl 3 ): 36.7(C-1), 27.2(C-2), 77.9(C-3), 40.5(C-4), 50...

preparation Embodiment 3L

[0051] Synthesis of Preparation Example 3LQC-X3

[0052] Weigh about 4.54g (0.01mol) of LQC-X1, dissolve it in 500ml of dichloromethane, add 200mg of Eosiy (alcohol solution), ventilate, and react with light for 10h. After the reaction, wash twice with 3 times the amount of saturated sodium bicarbonate solution, wash with water until neutral, remove water with anhydrous sodium sulfate, recover dichloromethane, pass through a silica gel column, and elute with petroleum ether: ethyl acetate = 5:1 . The LQC-X3 reaction yield was about 10%.

[0053] LQC-X3 related spectral data:

[0054] 1 H-NMR (500MHZ, CDCl 3 ): 0.83, 0.96, 0.99, 1.03, 1.05, 1.20, 1.21 (3H, each, s, 7×CH 3 ), 3.22(1H, m, H-3), 4.33(1H, d, J=2.5HZ, H-11), 5.38(1H, d, J=2.5HZ, H-12), 1.000~2.500(24H , the methylene and methine hydrogen signals in the triple core structure);

[0055] 13 C-NMR (500MHZ, CDCl 3 ): 37.0(C-1), 27.2(C-2), 78.4(C-3), 39.3(C-4), 50.8(C-5), 17.6(C-6), 34.2(C-7) , 37.7(C-8), 78.9(C...

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Abstract

The invention relates to the field of chemical and biological sciences, in particular to LQC-X structural formula I, and synthesis and application of intermediate of LQC-X, wherein a maximum dosage of LQC-X6 given to an mouse is 2000 mg / kg once in one day; the mouse is continuously observed for 7 days; no toxic reaction appears, and the medicine is proven to have quite high safety; and it is proved through pharmacodynamics experiments that LQC-X compounds have obvious anti-hepatitis B virus action and liver protecting and transaminase lowering action. The compounds can be used for preparing medicines for preventing and treating diseases of hepatitis B, chronic liver cirrhosis and the like. The structural formula I of LQC-X is shown in the description.

Description

technical field [0001] The present invention relates to the fields of chemistry and biological sciences, in particular to the synthesis and application of LQC-X structural general formula I and its intermediates, wherein LQC-X6 mice have a single daily single maximum dose of 2000 mg / kg and are continuously observed for 7 days , no toxic reaction occurred, indicating that the safety of the drug is very high, and pharmacodynamic experiments have proved that this type of compound has obvious anti-hepatitis B virus effect and liver-protecting and enzyme-reducing effect. It can be used to prepare medicines for preventing and treating diseases such as hepatitis B and chronic liver cirrhosis. [0002] [0003] LQC-X Structural Formula I [0004] Background technique [0005] Hepatitis B virus (Hepatitis B virus, HBV) and the resulting liver cirrhosis and liver cancer are one of the major diseases that threaten human life and health. At present, there is no effective treatmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07J71/00A61K31/56A61K31/58A61P31/20A61P1/16
Inventor 雷海民任健王鹏龙蔡程科李强程云
Owner 北京鸿测科技发展有限公司
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