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An indole amide compound that can selectively inhibit gastric cancer cells

A compound and selected technology, applied in the fields of drug combination, organic chemistry, organic active ingredients, etc., can solve the problem of less selective inhibition of gastric cancer, and achieve the effect of broadening the scope and good development prospects.

Inactive Publication Date: 2020-11-03
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a series of indole compounds that can be used to treat gastric cancer have been reported in the prior art, the compounds usually have inhibitory effects on multiple cancer cells at the same time, and there are few drugs that selectively inhibit gastric cancer.

Method used

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  • An indole amide compound that can selectively inhibit gastric cancer cells
  • An indole amide compound that can selectively inhibit gastric cancer cells
  • An indole amide compound that can selectively inhibit gastric cancer cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] N-(2-(1H-indol-3-yl)ethyl)-2-hydroxy-3-methylbenzamide (Compound R2)

[0046]

[0047]Step 1: Add aniline (9.3g, 0.1mol) and dilute hydrochloric acid to a 200ml round bottom flask, and add 30ml of a solution containing (7.3g, 0.105mol) sodium nitrite dropwise into the solution. After reacting for 1 hour, the clear liquid was filtered out and added dropwise to 70ml (37.8g, 0.3mol) of sodium sulfite solution, reacted at 80°C for 2 hours, then added dropwise about 25ml (0.3mol) of concentrated hydrochloric acid, reacted at 95°C for 2 hours, then placed in After overnight at room temperature, 12.6 g of solid phenylhydrazine hydrochloride was precipitated. Yield: 87.1%.

[0048] Step 2: Add (12.6g, about 0.087mol) phenylhydrazine hydrochloride, (21.1g, 0.10mol) sodium 4-chloro-1-hydroxy-butanesulfonate obtained in step 1 to a 200ml round bottom flask successively, 40ml of ethanol, 40ml of water, and then use disodium hydrogen phosphate solution to adjust the pH of the s...

Embodiment 2-5

[0051] With reference to the method of Example 1, compounds R3-R6 were prepared, and the corresponding data are as follows:

[0052]

[0053] compound R (n=1) Melting point / ℃ 1 H NMR

Embodiment 6

[0054] Example 6 In Vitro Activity Test

[0055] The cell lines are MGC-803 (human gastric cancer cells), HepG2 (human liver cancer cells), MCF-7 (human breast cancer cells), A549 (human lung cancer cells) and HELA (human cervical cancer cells).

[0056] The culture medium is DMEM+15% NBS+ double antibody

[0057] Sample solution preparation: After dissolving with DMSO (Merck), the concentration is 33333.33μmol / L

[0058] 1. In the middle plate, add the cell suspension to the 96-well plate, 100 μl per well (the cell content in each well is about 8000 cells / well), and incubate in a 37°C, 5% CO2 incubator for 24 hours;

[0059] 2. Add drug-use medium to prepare the gradient concentration of the sample solution (256, 128, 64, 32, 16, 8, 4, 2 μmol / L), discard the original medium on the 96-well plate, and add different concentrations of drugs to culture base, 100 μL per well, and 5 auxiliary wells for each concentration. For the remaining wells, use the medium containing 3‰ DMSO...

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Abstract

The invention discloses an indolamide compound capable of selectively inhibiting gastric cancer cells. The compound is capable of inhibiting the gastric cancer cells, particularly MGC-803 (human gastric cancer cells) cell strains, therefore the compound can be used as medicines for the selectively treatment of gastric cancer and has better developing prospect.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a series of indole amide compounds, their preparation methods and uses. Background technique [0002] Gastric cancer is a malignant tumor that occurs in gastric epithelial tissue, and its incidence rate ranks first among all kinds of tumors in my country. The disorder of the apoptosis regulation system in the multi-step transformation process of the occurrence and evolution of gastric cancer is one of the important reasons for the malignant phenotype of cells. [0003] Indole compounds are an important class of heterocyclic compounds with a wide range of biological activities. Indole secondary metabolites widely exist in cruciferous vegetables and a large number of marine organisms and actinomycetes. In recent years, its anticancer activity has attracted widespread attention. Currently, SU11248 (trade name: sunitinib), vinblastine (VLB, Vinblastine), vincristine (VCR, Vincri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14A61K31/4045A61P35/00
CPCA61P35/00C07D209/14
Inventor 唐国涛熊润德邓湘萍贺冬秀雷小勇
Owner NANHUA UNIV