Tripterine derivative and application thereof

A halogen and compound technology, applied in the field of medicine, can solve problems such as complex etiology of cancer, toxic and side effects of anticancer drugs, and easy drug resistance

Active Publication Date: 2019-01-04
LIAOCHENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of anticancer drugs are currently available clinically, the etiology of cancer is complex and prone to drug resistance, and

Method used

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  • Tripterine derivative and application thereof
  • Tripterine derivative and application thereof
  • Tripterine derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0054] Example 1

[0055] X is Y is n=2; Ar is different R 1 When substituted phenyl, the preparation of compounds I-1~I-12

[0056] Step A:

[0057]

[0058] Weigh 5mmol substituted trans-cinnamic acid derivative 1, and slowly add 10ml SOCl 2 , Stirring at room temperature for 1h, if the reactant does not dissolve, heat to 40℃ and stir for 0.5h, evaporate the solvent to obtain substituted cinnamic acid chloride; then add a small amount of anhydrous dichloromethane to dissolve, transfer the resulting solution to a constant pressure dropping funnel In the medium, weigh 10mmol piperazine and dissolve it in 20ml glacial acetic acid, slowly add the solution in the constant pressure dropping funnel to the piperazine dropwise, and stir at room temperature for 2 hours. The reaction solution was adjusted to pH 7-9 with 40% NaOH, extracted with dichloromethane three times, the organic phases were combined, and the organic phases were washed three times with saturated NaCl, dried over anhyd...

Example Embodiment

[0075] Example 2

[0076] X is Y is n=2; Ar is different R 1 When substituted phenyl, the preparation of compounds I-13~I-24

[0077] Step A:

[0078]

[0079] Weigh 5mmol substituted trans-cinnamic acid derivative 1, and slowly add 10ml SOCl 2 , Stir at room temperature for 1h, if the reactant does not dissolve, heat to 40℃ and stir for 0.5h, evaporate the solvent to obtain the substituted cinnamic acid chloride, then add 10ml of anhydrous dichloromethane to dissolve it, add 3ml of methanol dropwise, stir at room temperature for 10min, Concentrate under reduced pressure to obtain compound 4; add 20ml of ethylenediamine to the obtained compound 4, react under reflux for 2h, let cool to room temperature, pour the reaction solution into water, extract 3 times with ethyl acetate, combine the organic phases, and saturate the organic phases Washed with NaCl 3 times, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a yellow oil with a yield of 52-73...

Example Embodiment

[0093] Example 3

[0094] The inhibitory effect of tripterygium wilfordii derivative of the present invention on tumor cell growth

[0095] The MTT method was used to detect the growth inhibitory effects of ovarian cancer cells SKOV-3 and OVCAR3. 2×10 3 The cells were seeded in a 96-well plate and allowed to adhere to the wall and grow for 48 hours before adding test drugs of various concentrations. After incubation, add 50μLMTT solution (2mg / mL) to each well, continue to incubate for 4h, shake the plate to remove the culture solution, add DMSO, and measure the absorbance at 570nm. The cell growth inhibition rate caused by the test drug was obtained by the ratio of absorbance (%) between the drug-added group and the blank control group, and the IG was calculated 50 , The results are shown in Table 1.

[0096] Table 1. Growth inhibitory activity of compounds on tumor cells

[0097]

[0098]

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Abstract

The invention provides a tripterine derivative as well as a preparation method and application thereof. The tripterine derivative is a compound of formula I as shown in the description, or a medicallyacceptable salt thereof. In-vitro cell level activity evaporation tests show that the compound of formula I, or the medically acceptable salt thereof, has high anti-tumor cell proliferation activity,and has a good inhibition function on tumor stem cells. Therefore, the invention further relates to application of the compound of formula I in preparing medicines for treating and/or preventing cancer.

Description

technical field [0001] The present invention belongs to the technical field of medicine, and in particular relates to tripteryglide derivatives with the activity of inhibiting tumor cells and pharmaceutically acceptable salts thereof, a preparation method of such derivatives, and a pharmaceutical composition containing the derivatives as active ingredients. and its use in preparing medicines for treating and / or preventing various cancers. Background technique [0002] The occurrence and development of malignant tumors is a multi-step and multi-stage complex process, which seriously threatens human health and life. Although a variety of anticancer drugs are currently available clinically, the etiology of cancer is complex, drug resistance is easy to develop, and due to the toxic and side effects of anticancer drugs, the existing drugs cannot meet the needs of proper treatment or individualized treatment. Cancer stem cells refer to a kind of tumor cell subpopulation with extr...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/58A61K31/56A61P35/00
CPCA61P35/00C07J63/008
Inventor 李晓静任少达王红敏刘文霞李宁柳仁民
Owner LIAOCHENG UNIV
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