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Indole-substituted thiazolo cyclohexane compound and antineoplastic applications thereof

A compound and anti-tumor drug technology, which is applied in the application field of thiazolocyclohexane derivatives and anti-tumor, and can solve the problems of cancer multidrug resistance, poor selectivity, toxic and side effects, etc.

Inactive Publication Date: 2013-11-27
ZHEJIANG PHARMA COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many traditional drugs for the treatment of cancer in our country. They have obvious therapeutic effects in clinical practice, but their disadvantages are: low specificity and poor selectivity, leading to obvious toxic and side effects, and prone to serious cancer multidrug resistance. drug phenomenon

Method used

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  • Indole-substituted thiazolo cyclohexane compound and antineoplastic applications thereof
  • Indole-substituted thiazolo cyclohexane compound and antineoplastic applications thereof
  • Indole-substituted thiazolo cyclohexane compound and antineoplastic applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Reaction raw materials: commercially available or self-made.

[0022] 1.90g (10mmol) of compound A and 2.75g (10mmol) of compound B were dissolved in 20mL of dry THF, and then 3.04g (30mmol) of Et 3 N, then stirred at room temperature until the reaction was complete (24-48 hours). The reaction mixture was poured into ice water, extracted with 50 mL×3 dichloromethane, the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated on a rotary evaporator to obtain a crude product of I, which was purified by column chromatography. The pure product of I was obtained as a white solid, mp.157-159°C; MS, m / z=385 ([M+H] + ).

Embodiment 2

[0024]

[0025] 1.90 (10 mmol) of compound A and 2.75 g (10 mmol) of compound B were dissolved in 20 mL of dry THF, and 3.88 g (30 mmol) of DIPEA were added, followed by reflux with stirring until the reaction was complete (within 10 hours). The reaction mixture was poured into ice water, extracted with 50 mL×3 dichloromethane, the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated on a rotary evaporator to obtain a crude product of I, which was purified by column chromatography. The pure product of I was obtained as a white solid, mp.157-159°C; MS, m / z=385 ([M+H] + ).

Embodiment 3

[0027] (1) Material

[0028] Cell lines: leukemia HL-60 cells, gastric adenocarcinoma SGC-7901 cells, breast cancer MCF-7 cells, and lung cancer A-549 cells were all purchased from Shanghai Cell Institute, Chinese Academy of Sciences.

[0029] Reagents: MTT, Amresco aliquots; DMEM medium, Gibco; calf serum, Lanzhou Minhai Biology; trypsin, Amresco aliquots; fluorouracil injection, 0.25g / 10ml (branch), Tianjin Jinyao Amino Acid Co., Ltd.

[0030] Instrument: ultra-clean bench, Suzhou Purification Equipment Factory; CO 2 Incubator, Thermo Company, model: HERA Cell150; inverted microscope, Carl Zeiss Company, model: Axiovert200; enzyme-linked immunoassay instrument, TECAN Company, model: Sunrise; centrifuge, Kerdro Company, model: Heraeus.

[0031] (2) method

[0032] Cell culture: Tumor cells were inoculated in DMEM medium containing 10% calf serum, 100IU / ml penicillin G sodium salt and 100ug / ml streptomycin sulfate, placed at 37°C, 100% relative humidity, containing 5% CO 2 ...

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PUM

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Abstract

The invention relates to the field of anticancer related medicines, and particularly relates to an indole-substituted thiazolo cyclohexanea compound having antineoplastic activity and having a structure shown as the formula I, a preparation method thereof, pharmaceutical compositions thereof and applications thereof.

Description

technical field [0001] The invention relates to the field of anti-tumor related drugs. Specifically, the present invention relates to thiazolocyclohexane derivatives with antitumor effects, their preparation methods, pharmaceutical compositions containing them and their antitumor application. Background technique [0002] Cancer is the primary disease that threatens human life. According to statistics, the total number of cancer deaths in the world reaches 7 million every year. In my country, more than 1 million patients die of tumors every year, and gradually increase. It has become the first cause of death in urban population. At present, there are many traditional drugs for the treatment of cancer in our country, and they have obvious therapeutic effects in clinical practice, but their disadvantages are: low specificity and poor selectivity, leading to obvious toxic and side effects, and prone to serious cancer multidrug resistance drug phenomenon. [0003] With the dev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A61K31/428A61P35/00
Inventor 郭章华
Owner ZHEJIANG PHARMA COLLEGE
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