Indanone imine derivatives as well as preparation method and application thereof

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 sex, good inhibitory effect

Active Publication Date: 2021-08-24
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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  • Indanone imine derivatives as well as preparation method and application thereof
  • Indanone imine derivatives as well as preparation method and application thereof
  • Indanone imine derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation of embodiment 1 indanone imine derivatives

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

[0040]

[0041] In the formula, the R 1 is hydrogen, fluorine, chlorine, bromine; R 2 hydrogen, fluorine, chlorine, trifluoromethyl, methoxycarbonyl.

[0042] The preparation method of indanone imine derivatives is specifically: the diazo compound (0.20mmol) shown in formula SI-1 in the above reaction formula, the benzisoxazole (0.24mmol) shown in formula SI-2 and catalyst [2-(Dicyclohexylphosphine)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-diphenyl]bis(trifluoromethanesulfonyl Amine) gold (0.01mmol) 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; the reaction solution was Filtration, separation and purification by column chromatog...

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 determination are: colorectal adenocarcinoma cells (HCT-116) (purchased from Guangzhou Saiku Biotechnology Co., Ltd.).

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

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

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

Embodiment 3

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

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

[0076] 2. The inhibitory effect of indanone imine derivatives on human osteosarcoma cell proliferation was determined by CCK-8 method, 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 (5000 cells / well for inoculation), and add 100 μL of cell culture solution without cells to the blank well as a control, and inoculate the well The 96-well culture plate was pre-incubated for 24 hours in an incubator (37°C, 5% CO 2 );

[0078] 2) Add 1.0 μL of a solution of the compound to be tested (compounds I-1 to 8) dissolved in DMSO to the culture plate so that the final concentration is 20 μM, where...

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Abstract

The invention belongs to the technical field of medicinal chemistry, and particularly relates to indanone imine derivatives and a preparation method and application thereof. The structures of the indanone imine derivatives are as shown in a general formula (I) which is described in the specification. In the general formula (I), R1 is selected from hydrogen, fluorine, chlorine and bromine; and R2 is selected from hydrogen, fluorine, chlorine, a trifluoromethyl group and a methoxycarbonyl group. The derivatives are novel in structure, have very good anti-tumor effects, particularly show a very good inhibition effect on colorectal adenocarcinoma cells, osteosarcoma cells and breast cancer cells, have a very great application value in the aspect of the anti-tumor effect, and are expected to be made into anti-tumor drugs, especially drugs for resisting colorectal cancer cells, osteosarcoma cells and breast cancer cells; and meanwhile, the preparation method of the indanone imine derivatives has the advantages of few reaction steps, simplicity and safety in operation, low cost, less generated waste, high atom economy and high yield.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular 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 relevant statistics from the China Cancer Management Center, the incidence and death of malignant tumors in China have shown an upward trend in recent years. According to the 2018 global cancer statistics report of the official journal of the American Cancer Society "Journal of Cancer for Clinicians", the cancers with the largest number of new cases and deaths are lung cancer, breast cancer, prostate cancer, colon cancer, non-melanoma of the skin, gastric cancer, Liver cancer, rectal cancer, etc. Clinically, drug therapy is still the main treatment for tumors. However, the anti-tumor drugs currently used in clinical practice are far from meeting the req...

Claims

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Application Information

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Patent Type & Authority Applications(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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