3-(4-phenyl-1H-imidazolyl-5-yl)-1H-indole derivatives, and preparation method and application thereof

A technology of indole derivatives and phenyl, which is applied in the field of 3--1H-indole derivatives and its preparation, can solve the problems of insufficient curative effect, large toxic and side effects, and low cure rate, and achieve good proliferation activity, Good anti-tumor cell proliferation activity

Active Publication Date: 2016-08-31
浙江泽天精细化工有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Malignant tumors seriously endanger human health. Although surgery, chemotherapy, radiotherapy, etc. can be used for comprehensive treatment, the cure rate is still low. At present, there are many anti-tumor drugs that have been studied at home and abroad, and more than 60 kinds are commonly used in clinical practice, but the curative effect is not enough High, toxic and side effects are relatively large, and it is still a research hotspot for scientists to continue to search for drugs with high efficiency and low toxicity

Method used

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  • 3-(4-phenyl-1H-imidazolyl-5-yl)-1H-indole derivatives, and preparation method and application thereof
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  • 3-(4-phenyl-1H-imidazolyl-5-yl)-1H-indole derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Preparation of 6-chloro-1-(4-methoxy)-1H-indole.

[0043]

[0044]Sodium ethoxide solid (6.5g, 64mmol) was dissolved in DMF (25mL), stirred in an ice bath at 4°C, 6-chloro-indole (6.5g, 43mmol) was slowly dissolved in DMF (10mL), dripped at normal pressure A solution of p-methoxybenzyl chloride (6.5 mL, 47 mmol) in DMF (5.0 mL, 65 mmol) was added to the funnel. The reaction was carried out at room temperature, and the reaction was monitored by TLC until the raw materials were completely reacted. Pour into water, extract with ethyl acetate, take the ethyl acetate layer, wash with saturated brine, dry over anhydrous sodium sulfate, recover the solvent, and perform silica gel column chromatography on the obtained crude product with ethyl acetate:petroleum ether ratio of 1:12, 7.0 g of the product was obtained with a yield of 60.05%. m / z=271.08[M+H] + .

Embodiment 2

[0045] Embodiment 2: Preparation of chlorine-substituted 2-oxo-2-phenylacetaldehyde

[0046]

[0047] Dimethylsulfoxide (80.03mL, 1126mmol) and 4.25mL 1-(4-chlorophenyl)ethanone were poured into a round bottom flask and shaken gently. Iodine solid (16.5 g, 66 mmol) was quickly added, shaken gently, and dissolved. Add the remaining dimethyl sulfoxide, stir in an 80°C oil bath, and reflux for about 1 hour. The reaction was monitored by TLC until the starting material was completely reacted. Pour into water, dissolve 31.4g of sodium thiosulfate pentahydrate solid in 168.6g of water, stir to dissolve, and pour into the mixed solution. Ethyl acetate was separated and extracted, and the ethyl acetate layer was taken, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was recovered, and the crude product was recrystallized in a solvent of ethyl acetate:petroleum ether at a ratio of 1:12. Vacuum filtration under reduced pressure yielded the pure p...

Embodiment 3

[0048] Example 3: Preparation of 1‐(6‐chloro‐1‐(4‐methoxybenzyl)‐1H‐indol‐3‐yl)‐2‐(4‐chlorophenyl)ethane‐1,2‐ diketone.

[0049]

[0050] Compound 2 (2.0 g, 7 mmol) and compound 4 (1.0 g, 6 mmol) were dissolved in toluene (31.3 mL) and stirred in an oil bath at 110°C. The reaction was monitored by TLC until the starting material was completely reacted. Spin dry to recover toluene to obtain a black viscous reaction product, add water, extract with ethyl acetate, collect the ethyl acetate layer, wash with saturated brine, dry over anhydrous sodium sulfate, and recover the solvent to obtain a crude product. The polarity of the solvent (ethyl acetate:petroleum ether: 1:15) was increased to 1:5, and silica gel column chromatography was performed to obtain 1.0 g of the product with a yield of 40.74%.

[0051] Product Confirmation: m / z=437.06[M+H] + ; 1 H NMR (400MHz, CDCl 3 ): δ: 7.238(dd, J=2.69Hz, 2H, Ar-H), 7.020-7.080(m, J=11.89Hz, 3H, Ar-H), 6.808-6.845(d, J=4.03Hz, 4H ...

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Abstract

The invention discloses 3-(4-phenyl-1H-imidazolyl-5-yl)-1H-indole derivatives, and a preparation method and application thereof, belonging to the technical field of heterocyclic compounds. The N-piperidyl formacyl group with unique biological activity is creatively introduced into the imidazole-indole system, and the halogen atom with unique biological activity is introduced into the 3-(4-phenyl-1H-imidazolyl-5-yl)-1H-indole system, so that the synthesized 3-(4-phenyl-1H-imidazolyl-5-yl)-1H-indole derivatives have favorable anti-tumor cell proliferation activity. The 3-(4-phenyl-1H-imidazolyl-5-yl)-1H-indole derivatives can be further modified to be used as a novel antineoplastic drug, have favorable anti-non-small cell lung cancer (A549) proliferation activity, and can be used as a new drug for resisting non-small cell lung cancer and human colonic adenocarcinoma.

Description

Technical field: [0001] The invention relates to a 3-(4-phenyl-1H-imidazol-5-yl)-1H-indole derivative, a preparation method and application thereof, and belongs to the technical field of heterocyclic compounds. Background technique: [0002] With the change of living environment and style, the aging of the population, and the increase of survival pressure, the incidence of malignant tumors in my country continues to rise, and malignant tumors have become the leading cause of death. Malignant tumors seriously endanger human health. Although surgery, chemotherapy, radiotherapy, etc. can be used for comprehensive treatment, the cure rate is still low. At present, there are many anti-tumor drugs that have been studied at home and abroad, and there are no less than 60 commonly used clinically, but the curative effect is not enough High, toxic and side effects are relatively large, and it is still a research hotspot for scientists to continue to search for high-efficiency and low-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04A61K31/4178A61K31/496A61P35/00
CPCC07D403/04
Inventor 胡纯琦
Owner 浙江泽天精细化工有限公司
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