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Indole derivative containing diazole, triazole and pyrazole structural units and application thereof

A technology of indole derivatives and structural units, applied in the field of indole derivatives, can solve the problem that the serious threat of cancer to human health has not been effectively controlled.

Active Publication Date: 2021-12-07
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The serious threat of cancer to human health has not been effectively controlled

Method used

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  • Indole derivative containing diazole, triazole and pyrazole structural units and application thereof
  • Indole derivative containing diazole, triazole and pyrazole structural units and application thereof
  • Indole derivative containing diazole, triazole and pyrazole structural units and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the preparation of 3-(1H-indol-3-yl)-3-oxo-propionitrile

[0046] Put indole (10.00g, 85.36mmol), cyanoacetic acid (10.17g, 119.50mmol) and 100mL acetic anhydride in a 250mL round bottom flask successively, and reflux at 40°C for 4h. After the reaction, it was cooled to room temperature, filtered with suction, washed with methanol for 2-3 times, and dried to obtain a white solid with a yield of 77.3%.

Embodiment 2

[0047] Example 2: Preparation of 3-(1H-indol-3-yl)-1H-pyrazol-5-amine

[0048] Add 3-(1H-indol-3-yl)-3-oxo-propionitrile (5.00g, 27.14mmol) and 80% hydrazine hydrate (6.79g, 169.38mmol) successively in a 500mL round bottom flask, Then add about 250 mL of absolute ethanol as a solvent, reflux and stir at 80°C, and monitor the reaction system by TLC. After the reaction was finished, let stand and cool naturally. The reaction mixture was concentrated under reduced pressure to a thick state, cooled, filtered with suction, and washed with ethyl acetate for 2-3 times to obtain a brown solid with a yield of 54.1%.

Embodiment 3

[0049] Example 3: Preparation of N-(3-(1H-indol-3-yl)-1H-pyrazol-5-yl)-2-chloroacetamide

[0050] Add 3 (2.00g, 10.09mmol) and anhydrous sodium carbonate (1.07g, 10.69mmol) respectively into a 50mL round bottom flask, add a part of 1,4-dioxane, and stir at room temperature. Then chloroacetyl chloride (1.14g, 10.09mmol) was dissolved in 2mL of 1,4-dioxane (20mL in total), and added dropwise into the round bottom flask, and the stirring was continued for 1h. After the reaction was monitored by TLC, take another beaker and add 100 mL of water, add NaCl, then pour crushed ice into the reaction mixture, stir until precipitation occurs, let stand, filter under reduced pressure, and wash with water to obtain a gray-green solid. After drying, recrystallization from ethanol afforded 4. White solid, 18% yield.

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Abstract

The invention relates to an indole derivative structure containing diazole, triazole and pyrazole structural units and application of the indole derivative structure. The compound has a structure as shown in a general formula (I), wherein X is O, S or N-NH2. Indole is used as a mother nucleus, pyrazole is introduced to the site 3, a series of indole derivatives containing diazole, triazole and pyrazole structures are synthesized, and the compounds have good cytotoxicity to human liver cancer cells HepG2, human non-small cell lung cancer cells A549, human prostate cancer cells PC-3 and human chronic myeloid leukemia cells K562.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a class of indole derivative structures containing oxadiazole, triazole and pyrazole structural units and applications thereof. Background technique [0002] Due to the influence of many factors such as the environment, the incidence of malignant tumors is increasing year by year, and cancer has become the second largest killer of human health. The serious threat of cancer to human health has not been effectively controlled. Therefore, it is very important to research and develop new anticancer drugs with low toxicity and high efficiency. [0003] The indole structure is commonly found in natural and synthetic drugs, and has biological activities such as antitumor, antioxidation, and antibacterial. Introducing different substituents at the 3-position of indole to modify and modify the structure has always been a hot spot in drug research. Rucaparib (Rucaparib), Osi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C07D417/14C07D403/14C07D401/14A61K31/4245A61K31/433A61K31/4439A61K31/4196A61P35/00A61P35/02
CPCC07D413/14C07D417/14C07D403/14C07D401/14A61P35/00A61P35/02
Inventor 欧阳贵平王贞超唐震华张广龙樊思莉胡伟男王钦
Owner GUIZHOU UNIV
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