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1,3-diazacyclo[1,2-a]quinoline compound, its preparation method and anti-tumor application

A technology of diaza rings and compounds, applied in the field of medicinal chemistry, to achieve the effects of molecular diversity, product stability, and simple synthesis process

Active Publication Date: 2018-10-30
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is currently no alternative treatment for 5-fluorouracil-based combination chemotherapy ineffective

Method used

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  • 1,3-diazacyclo[1,2-a]quinoline compound, its preparation method and anti-tumor application
  • 1,3-diazacyclo[1,2-a]quinoline compound, its preparation method and anti-tumor application
  • 1,3-diazacyclo[1,2-a]quinoline compound, its preparation method and anti-tumor application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Synthesis of 4-(4-fluorobenzoyl)-7-nitro-1,2-dihydroimidazo[1,2-a]quinoline (compound 1)

[0060] Add 1-(4-fluorophenyl)-2-(imidazolidin-2-ylidene)ethan-1-one (1 mmol) and 2-fluoro-5-nitrobenzaldehyde to a 25 mL round bottom flask (3 mmol), 1,4-dioxane (15 ml) and piperidine (1 mmol) were added and heated to 65°C under magnetic stirring for 2 hours of reaction. After filtration, the precipitate was washed with a mixed solvent of petroleum ether / dichloromethane=10:1 to obtain a yellow flocculent solid. Take the yellow solid, add chloroform and saturated aqueous sodium bicarbonate solution, extract the organic phase and wash it with saturated aqueous sodium chloride solution, collect the chloroform and dry it with anhydrous sodium sulfate, evaporate part of the solvent, add petroleum ether for recrystallization, After filtration and drying, a yellow solid product 4-(4-fluorobenzoyl)-7-nitro-1,2-dihydroimidazo[1,2-a]quinoline (compound 1) was obtained with a yi...

Embodiment 2

[0064] Example 2: Synthesis of 5-(4-chlorobenzoyl)-7,8,10-trifluoro-2,3-dihydro-1H-pyrimido[1,2-a]quinoline (compound 2)

[0065] In a 25 mL round bottom flask was added 1-(4-chlorophenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one (1 mmol, 0.44 g) and 2,3 , 5,6-tetrafluorobenzaldehyde (3 mmol, 0.44 g), 1,4-dioxane (15 mL) was added as a solvent, catalyst piperidine (0.5 mmol) and anhydrous calcium chloride were added (0.5 mmol) was heated to 110° C. under magnetic stirring, and reacted for 12 hours. After filtration, the precipitate was washed with a mixed solvent of petroleum ether / ethyl acetate = 10:1, and then the precipitate was taken out, dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, and the organic phase was washed with saturated aqueous sodium chloride solution. Collect the ethyl acetate and dry it with anhydrous sodium sulfate. After evaporating part of the solvent, add an appropriate amount of petroleum ether until a pr...

Embodiment 3

[0070] Example 3: Synthesis of 5-(4-chlorobenzoyl)-8-(trifluoromethyl)-2,3-dihydro-1H-pyrimido[1,2-a]quinoline (compound 3)

[0071] In a 25 mL round bottom flask were added 1-(4-chlorophenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one (1 mmol) and 2-fluoro-5- After (trifluoromethyl)benzaldehyde (2 mmol), 1,4-dioxane (15 mL) was added as a solvent, the catalyst piperidine (0.5 mmol), and anhydrous calcium chloride (0.5 mol) was heated to 75°C under magnetic stirring, and reacted for 6 hours. After filtration, the precipitate was washed with a small amount of petroleum ether / chloroform=10:2 mixed solvent, and then the precipitate was dissolved in dichloromethane, and the organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. Afterwards, the chloroform was collected and dried with anhydrous sodium sulfate. Part of the solvent was evaporated and an appropriate amount of cyclohexane was added until a precipitat...

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Abstract

The invention relates to a 1,3-diazabicyclo [1,2-a] quinoline compound as well as a preparation method and antitumor application thereof, and belongs to the technical field of pharmaceutical chemistry. The structure of the compound is as shown in a formula (1) (as shown in the description), in the formula (1), Ar is phenyl, halogenated phenyl, alkyl-substituted phenyl, alkoxy group-substituted phenyl, trifluoromethyl-substituted phenyl, nitro-substituted phenyl, cyano-substituted phenyl or thienyl; R1-R4 are halogen atoms, hydrogen atoms, alkyl groups, trifluoromethyl, nitro or piperydyl, wherein n is 1 or 2 or 3. Ex-vivo human-derived tumor cell strain activity screening researches indicate that the compound disclosed by the invention has strong antineoplastic activity for five common tumor cell strains: HCT116, A549, HT29, SGC7901, and HepG2. The antineoplastic activity of most of compounds is higher than that of a positive control medicine namely cisplatin. The 1,3-diazabicyclo [1,2-a] quinoline compound disclosed by the invention has wide application prospects in the respect of preparing antitumor medicines.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a 1,3-diazacyclo[1,2-a]quinoline compound with antitumor activity, a preparation method thereof, and an application as an antitumor drug. Background technique [0002] With the development of society, environmental pollution and food problems are becoming more and more serious, and cancer has become the primary disease that endangers human health. Seeking an effective, low-toxic and easy-to-prepare anticancer drug has become the focus of drug research and development in various countries. Among them, the widely used cytotoxic anticancer drugs mainly include metal platinum complexes, alkylating agents, antibiotics and immune function regulators. [0003] Colon-rectal cancer is one of the most common malignant tumors in my country, and currently ranks fourth in the incidence of malignant tumors. In recent years, the incidence of colorectal cancer has shown ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61P35/00
CPCC07D471/04
Inventor 严胜骄林军陈亮张继红王玉玲
Owner YUNNAN UNIV
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