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Preparation of anti-tumor drug LQC-Y and application thereof

A compound and derivative technology, applied in the field of chemistry and biological sciences, can solve the problems of hematopoietic system and immune function damage, patient death, etc., and achieve the effect of increasing spleen index and inhibiting tumor growth

Active Publication Date: 2014-11-19
3D MEDICINES (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These treatments cause serious damage to the hematopoietic system and immune function of the human body, which can easily lead to the death of the patient.

Method used

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  • Preparation of anti-tumor drug LQC-Y and application thereof
  • Preparation of anti-tumor drug LQC-Y and application thereof
  • Preparation of anti-tumor drug LQC-Y and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0038] Preparation Example 1 The preparation of 2-bromomethyl-3,5,6-trimethylpyrazine intermediate

[0039] Dissolve 10 g of dehydrated ligustrazine in 60 ml of CCl 4 According to the molar ratio ligustrazine: NBS = 1:0.7, add NBS9.17g (a small amount of benzoyl peroxide can be added as a free radical initiator), under the irradiation of an incandescent lamp, reflux for 10-12h, cool and concentrate , in a water bath at 60-70°C under reduced pressure, the excess ligustrazine was pumped away, and the residue was placed in the refrigerator to stand still. 7.75 g of a light red semi-oil was obtained, with a yield of 70%.

preparation Embodiment 2

[0040] Synthesis of Preparation Example 2 LQC-Y1 (Compound 1)

[0041] Put 1.63mmol of 2-bromomethyl-3,5,6-trimethylpyrazine and 1.63mmol of cholic acid prepared in Example 1 into a 100ml three-necked flask, add 40ml of DMF and wait for the mixture to dissolve, then add 9mmol of anhydrous Potassium carbonate, stirred at 90°C for 4.5 hours, TLC monitored that the reaction raw materials basically disappeared, stop the reaction, add 250ml saturated sodium chloride solution to the reaction solution, extract three times with ethyl acetate, evaporate the combined extracts to dryness, redissolve the residue in a small amount of chloroform, add 3g of silica gel The mixed sample was evaporated to dryness under reduced pressure, and the eluent was petroleum ether: ethyl acetate: methanol = 20:3:1, and 0.44 g of white powder was obtained, with a yield of 50%, and a melting point of 67.9 to 68.8° C.; The carbon spectrum data are as follows:

[0042] 1 HNMR (500MHZ, CDCl 3 ): 0.670 (s, ...

preparation Embodiment 3

[0044] Preparation Example 3 Synthesis of LQC-Y2 (Compound 2)

[0045] 3.26mmol of 2-bromomethyl-3,5,6-trimethylpyrazine and 3.26mmol of deoxycholic acid prepared in Example 1 were placed in a 100ml three-necked bottle, and 40ml of DMF was added to dissolve the mixture, followed by 9mmol of Anhydrous potassium carbonate, stirred at 85°C for 4 hours, TLC monitors that the reaction materials basically disappear, stop the reaction, add 250ml saturated sodium chloride solution to the reaction solution, extract three times with ethyl acetate, evaporate the combined extracts to dryness, redissolve the residue in a small amount of chloroform, add 3g The silica gel was evaporated to dryness under reduced pressure and the mixed sample was eluted with petroleum ether:ethyl acetate=10:2.5 to obtain 1.0 g of light yellow oil with a yield of 58.4%. The hydrogen spectrum and carbon spectrum data of compound 2 are as follows:

[0046] 1 HNMR (500MHZ, CDCl 3 ): 0.652 (s, 3H, 18, -CH 3 ), ...

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Abstract

The invention discloses a structural formula of an LQC-Y as well as synthesis and an application thereof. Pharmacological experiments verify that the compound has a remarkable anti-tumor effect, wherein the single day maximum dosage of an LQC-Y3 mouse is 6000mg / kg. No toxic reactions happen within 14 days of continuous observation, thus, the drug is very high in safety and can be used for preparing drugs for preventing and treating cancers such as liver cancer and lung cancer. The structural formula of LQC-Y is as shown in the specification, wherein R represents sterides such as cholic acid, deoxycholic acid, ursodesoxycholic acid, chenodeoxycholic acid and hyodeoxycholic acid; triterpenoids such as oleanolic acid, ursolic acid, pachymic acid, glycyrrhetinic acid and glycosides; parietic acid, rheum emodin and other anthraquinone mother nucleus mono-substituted or multi-substituted structures; baicalein, baicalin and other flavone analogue compounds; shikimic acid, mono-substituted shikimic acid or multi-substituted shikimic acid; geniposidic acid and other iridoid acid derivatives; and paeonol, curcumin and structural derivatives.

Description

[0001] This application is a divisional application, the parent application number is 201110055102.X, the application date is March 9, 2011, and the invention name is "Preparation and Application of Anti-tumor Drug LQC-Y". technical field [0002] The present invention relates to the fields of chemistry and biological sciences, in particular to the general structural formula of LQC-Y and its synthesis and application. Pharmacological experiments have proved that this type of compound has obvious anti-tumor effects, and LQC-Y3 mice are given the maximum dosage in a single day 6000mg / kg, within 14 days of continuous observation, no toxic reaction occurs, indicating that the drug is very safe and can be used to prepare drugs for preventing and treating cancers such as liver cancer and lung cancer and immune diseases. [0003] [0004] Among them, R represents cholic acid, deoxycholic acid, ursodeoxycholic acid, chenodeoxycholic acid, hyodeoxycholic acid and other steroidal comp...

Claims

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Application Information

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IPC IPC(8): C07J43/00C07J63/00C07D241/12C07D405/14A61K31/58A61K31/4965A61K31/497A61P35/00A61P1/16
Inventor 雷海民封卫毅王鹏龙郭晶李强蔡程科陈大刚
Owner 3D MEDICINES (SHANGHAI) CO LTD
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