A kind of indanone imine derivative and its preparation method and application

A technology of derivatives and imines, which is applied in the field of indenone imine derivatives and their preparation, can solve the problems of lack of effective treatment of tumors and anti-tumor drugs that cannot meet the treatment requirements, and achieve good anti-tumor effects and high atomic economy The effect of novelty and structure

Active Publication Date: 2022-06-28
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the anti-tumor drugs currently used in clinical practice are far from meeting the requirements of treatment, and there is still a lack of effective drugs for the treatment of tumors.

Method used

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  • A kind of indanone imine derivative and its preparation method and application
  • A kind of indanone imine derivative and its preparation method and application
  • A kind of indanone imine derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Preparation of indanone imine derivatives

[0039] The preparation method of indanone imine derivative is carried out according to the following reaction formula:

[0040]

[0041] where the R 1 For hydrogen, fluorine, chlorine, bromine; R 2 For hydrogen, fluorine, chlorine, trifluoromethyl, methoxycarbonyl.

[0042] The specific preparation method of the indanone imine derivative is as follows: the diazo compound (0.20 mmol) represented by the formula SI-1 in the above reaction formula, the benzisoxazole (0.24 mmol) represented by the formula SI-2 and a catalyst [2-(Dicyclohexylphosphine)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-diphenyl]bis(trifluoromethanesulfonylidene) Amine) gold (0.01 mmol) was weighed in a test tube, then 2 mL of anhydrous 1,2-dichloroethane was added to the reaction system, and the reaction was stirred at 60 ° C for 24 hours until the diazo compound was completely consumed; Filtration, column chromatography separation and purifi...

Embodiment 2

[0055] Example 2 Inhibitory activity of indanone imine derivatives on colorectal adenocarcinoma cells

[0056] 1. The human colorectal adenocarcinoma cells used in the assay are colorectal adenocarcinoma cells (HCT-116) (purchased from Guangzhou Saiku Biotechnology Co., Ltd.).

[0057] 2. The CCK-8 method was used to determine the inhibitory effect of indanone imine derivatives on the proliferation of human colorectal adenocarcinoma cells, wherein the specific determination process of the inhibition rate of HCT-116 cells was as follows:

[0058] 1) Add 100 μL of cell suspension prepared with complete medium to the 96-well plate (the cell inoculation amount is 5000 cells / well), and add 100 μL of cell culture medium without cells to the blank well as a control. The 96-well culture plate was pre-incubated in an incubator (37°C, 5% CO) for 24 hours. 2 );

[0059] 2) Add 1.0 μL solution of the compounds to be tested (compounds I-1 to I-8) dissolved in DMSO to the culture plate to...

Embodiment 3

[0074] Example 3 Inhibitory activity of indanone imine derivatives on osteosarcoma cells

[0075] 1. The human osteosarcoma cells used in the assay are: human osteosarcoma cells (SJSA-1) (purchased from Guangzhou Saiku Biotechnology Co., Ltd.).

[0076] 2. The CCK-8 method was used to determine the inhibitory effect of indanone imine derivatives on the proliferation of human osteosarcoma cells, wherein the specific determination process of the inhibition rate of SJSA-1 cells was as follows:

[0077] 1) Add 100 μL of cell suspension prepared with complete medium to the 96-well plate (the inoculation amount of cells is 5000 cells / well), and add 100 μL of cell culture medium without cells to the blank well as a control. The 96-well culture plate was pre-incubated in an incubator (37°C, 5% CO) for 24 hours. 2 );

[0078] 2) Add 1.0 μL solution of the compounds to be tested (compounds 1-1 to 8) dissolved in DMSO to the culture plate to make the final concentration 20 μM, and add ...

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Abstract

The present invention belongs to the technical field of medicinal chemistry, and specifically relates to an indenone imine derivative and its preparation method and application. The structure of the indenone imine derivative is shown in the general formula (I), wherein the R 1 selected from hydrogen, fluorine, chlorine, bromine; R 2 Selected from hydrogen, fluorine, chlorine, trifluoromethyl, and methoxycarbonyl; the derivative has a novel structure and has good antitumor effects, especially for colorectal adenocarcinoma cells, osteosarcoma cells, and breast cancer cells Inhibition of anti-tumor effect has great application value, and it is expected to be prepared as anti-tumor drug, especially anti-colorectal cancer cell, osteosarcoma cell and breast cancer cell drug; meanwhile, the indenone imine The preparation method of the derivative has fewer reaction steps, simple and safe operation, low cost, less waste generation, and has the advantages of high atom economy and high yield.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and particularly relates to an indanone imine derivative and a preparation method and application thereof. Background technique [0002] Malignant tumors are one of the diseases that pose a great threat to human health. According to the statistics of the China Cancer Management Center, the incidence and mortality of malignant tumors in China have been on the rise in recent years. According to the 2018 Global Cancer Statistics Report by the Journal of Clinician Cancer, the official journal of the American Cancer Society, the cancers with the largest number of new cases and deaths are lung cancer, breast cancer, prostate cancer, colon cancer, skin non-melanoma, stomach cancer, Liver cancer, rectal cancer, etc. Clinically, the treatment of tumors is still mainly drug therapy. However, the current clinically used antitumor drugs are far from meeting the treatment requirements, and there...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/02C07C251/20A61P35/00A61K31/216A61K31/235
CPCC07C249/02C07C251/20A61P35/00C07C2602/08
Inventor 徐新芳谢雄达鲍明黄晶晶张芷菁史滔达胡文浩
Owner SUN YAT SEN UNIV
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