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Derivatives of tripterine and their applications

A compound and pharmaceutical technology, applied in the field of medicine, can solve problems such as toxic and side effects of anticancer drugs, complex etiology of cancer, and existing drugs that cannot meet proper treatment or individualized treatment.

Active Publication Date: 2021-02-09
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 due to the toxic and side effects of anticancer drugs, the existing drugs cannot meet the needs of proper treatment or individualized treatment

Method used

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  • Derivatives of tripterine and their applications
  • Derivatives of tripterine and their applications
  • Derivatives of tripterine and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0056] Step A:

[0057]

[0058] Weigh 5mmol of substituted trans-cinnamic acid derivative 1, slowly add 10ml of SOCl 2 , stirred at room temperature for 1h, if the reactant is not dissolved, heat to 40°C and stir for 0.5h, evaporate the solvent to obtain substituted cinnamic acid chloride; then add a small amount of anhydrous dichloromethane to dissolve, and transfer the obtained solution to a constant pressure dropping funnel , weighed 10mmol piperazine and dissolved it in 20ml glacial acetic acid, slowly added the solution in the constant pressure dropping funnel dropwise to piperazine, and stirred at room temperature for 2h. The reaction solution was adjusted to pH 7-9 with 40% NaOH, extracted 3 times with dichloromethane, the organic phases were combined, washed 3 times with saturated NaCl, dried over anhydrous sodium sulfate, and concentrated under reduced p...

Embodiment 2

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

[0077] Step A:

[0078]

[0079] Weigh 5mmol of substituted trans-cinnamic acid derivative 1, slowly add 10ml of SOCl 2 , stir at room temperature for 1 hour, if the reactant is not dissolved, heat to 40°C and stir for 0.5 hour, evaporate the solvent to dryness to obtain substituted cinnamic acid chloride, then add 10ml of anhydrous dichloromethane to dissolve, add dropwise 3ml of methanol, and stir at room temperature for 10min. Concentrate under reduced pressure to obtain compound 4; add 20ml of ethylenediamine to the obtained compound 4, 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 use saturated Washed three times with NaCl, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a yellow oil with a yield of 52-73%.

[0080...

Embodiment 3

[0094] Inhibitory effect of tripterine derivatives of the present invention on tumor cell growth

[0095] MTT assay was used to detect the growth inhibitory effect of ovarian cancer cells SKOV-3 and OVCAR3. Will 2×10 3 Cells were inoculated in a 96-well plate, and allowed to adhere to the wall and grow for 48 hours before adding the test drugs at various concentrations. After culturing, add 50 μL of MTT solution (2 mg / mL) to each well, continue to incubate for 4 hours, shake the plate to remove the culture solution, add DMSO, and measure its absorbance at 570 nm. Obtain the cell growth inhibition rate caused by the test drug by the absorbance ratio (%) of the drug-dosed group and the blank control group, and calculate the IG 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, a preparation method and an application thereof. The tripterycin derivative is a compound of general formula I or a medically acceptable salt, and the in vitro cell-level activity evaluation test shows that the compound of general formula I involved in the present invention or a medically acceptable salt has better Anti-tumor cell proliferation activity, but also has a strong inhibitory effect on tumor stem cells. The present invention therefore also relates to the use of compounds of general formula I in the preparation of medicaments for the treatment and / or prevention of 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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Patent Type & Authority Patents(China)
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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