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2'-Aminochalcone azole compounds and their pyrazoline and cyclopropyl azole derivatives, preparation method and use

A technology of compound and application, applied in the fields of 2′-aminochalcone azole compounds and their pyrazoline and cyclopropylazole derivatives, antimicrobial and antitumor activities, capable of solving α-azolyl chalcone Less ketones and other problems

Inactive Publication Date: 2016-08-03
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the biological activity of α-azolyl chalcone compounds. It can be seen that the research on chalcone azole compounds has just started, so there is still more room for exploration in this field

Method used

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  • 2'-Aminochalcone azole compounds and their pyrazoline and cyclopropyl azole derivatives, preparation method and use
  • 2'-Aminochalcone azole compounds and their pyrazoline and cyclopropyl azole derivatives, preparation method and use
  • 2'-Aminochalcone azole compounds and their pyrazoline and cyclopropyl azole derivatives, preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1: Preparation of 2′,4′-difluoro-2-(1H-1,2,4-triazol-1-yl)acetophenone (referred to as compound 1)

[0068]

[0069] Add triazole (6.9g, 0.1mol) and potassium carbonate (13.8g, 0.1mol) into a 250mL round bottom flask, take an appropriate amount of acetonitrile as a solvent, and add 2′,4′-difluoro-2-chlorophenethyl Ketone (19.0 g, 0.1 mol). After the reaction, the solvent was evaporated to dryness, and an equal volume of water and chloroform was added to extract three times. The organic phase was washed with saturated ammonium chloride solution and distilled water, and dried over anhydrous sodium sulfate. After rotary evaporation and recrystallization, 14.5 g of light yellow solid was obtained, yield: 65%, melting point: 108-110°C (commercial product 107-111°C).

Embodiment 2

[0070] Example 2: (Z)-1-(4-fluoro-2-(piperidin-1-yl)phenyl)-3-phenyl-2-(1H-1,2,4-triazole-1- Base) prop-2-en-1-one (referred to as compound 2) and (Z)-1-(2,4-bis(piperidin-1-yl)phenyl)-3-phenyl-2-(1H Preparation of -1,2,4-triazol-1-yl)prop-2-en-1-one (compound 3 for short)

[0071]

[0072] In a 100mL single-necked flask, add an appropriate amount of toluene as a solvent, and then add 2′,4′-difluoro-2-(1H-1,2,4-triazol-1-yl)acetophenone (2.23g, 10mmol) , benzaldehyde (1.06g, 10mmol) and piperidine (1.87g, 22mmol), then add 3 drops of glacial acetic acid as a catalyst, install a water separator, keep stirring at 130°C under reflux, and the reaction is complete after 6 hours. Toluene was distilled off under reduced pressure, and an equal volume of water and chloroform were added to extract three times. The organic phase was dried over anhydrous sodium sulfate and then concentrated. Column chromatography was performed using petroleum ether and ethyl acetate (7 / 1, V / V) as elue...

Embodiment 3

[0075] Example 3: (Z)-1-(4-fluoro-2-morpholinophenyl)-3-phenyl-2-(1H-1,2,4-triazol-1-yl)propane-2 -en-1-one (referred to as compound 4) and (Z)-1-(2,4-dimorpholinophenyl)-3-phenyl-2-(1H-1,2,4-triazole- Preparation of 1-yl) prop-2-en-1-one (compound 5 for short)

[0076]

[0077] According to the synthetic method of embodiment 2. Starting materials are 2',4'-difluoro-2-(1H-1,2,4-triazol-1-yl)acetophenone (2.23g, 10mmol), benzaldehyde (1.06g, 10mmol) and Morpholine (1.91g, 22mmol) gave compound 4 (yellow solid, 2.09g, yield: 56%, melting point: 123-124°C) and compound 5 (red syrup, 0.84g, yield: 19%).

[0078] Compound 4: 1 HNMR (300MHz, CDCl 3 )δ: 8.11(s, 1H, trizole5-H), 8.06(s, 1H, trizole3-H), 7.49~6.70(m, 9H, C=CH, PhH), 3.77~3.74(t, 4H, J= 4.2Hz, morpholino OCH 2 ),3.01~2.98(t,4H,J=4.5Hz,morpholinoNCH 2 )ppm; MS(m / z):379[M+H] + .

[0079] Compound 5: 1 HNMR (300MHz, CDCl 3 )δ: 8.11(s, 1H, trizole5-H), 8.06(s, 1H, trizole3-H), 7.50~6.42(m, 9H, C=CH, PhH), 3.89...

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Abstract

The present invention relates to a class of 2'-amino chalcone azole compounds with structures represented by general formula (I, II, III, IV, XIII) and pharmaceutically acceptable salts thereof. The amine group is introduced into the chalcone skeleton. At the same time, the substitution of the azole ring at the α position is realized; a kind of pyrazoline derivatization based on the structure shown in the general formula (V, VI, VII, VIII, XIV, XV) based on 2'-amino chalcone azoles compounds and pharmaceutically acceptable salts thereof; a class of cyclopropylazole derivatives based on 2'-amino chalconazole compounds with structures shown in general formula (IX, X, XI, XII, XVI, XVII) and its pharmaceutically acceptable salt. The present invention relates to the antimicrobial and antitumor activities of 2'-amino chalcone azole compounds, pyrazoline derivatives, cyclopropyl azole derivatives and their pharmaceutically acceptable salts. The invention also relates to the medical use of these compounds.

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, in particular to the preparation, antimicrobial and antimicrobial properties of 2′-aminochalconazole compounds, pyrazoline and cyclopropylazole derivatives, and their pharmaceutically acceptable salts. tumor activity. The invention also relates to the medical use of these compounds. Background technique [0002] Chalcones are a class of naturally occurring open-chain flavonoids widely distributed in a variety of edible plants. Chalcone compounds have the following characteristics: i) typical acyclic acrylone structure, easy to synthesize and structure modification; ii) low intramolecular electron transfer but showing excellent nonlinear optical properties; iii) enone structure can be Specifically bind the sulfhydryl moiety of nucleic acid, thereby avoiding side effects such as mutagenesis and carcinogenesis; iv) chalcones and their metabolites can form conjugates with g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08C07D401/10C07D401/14C07D413/10C07D413/14C07D403/10C07D403/14C07D409/14A61K31/4196A61K31/4545A61K31/5377A61K31/496A61P31/04A61P31/10A61P35/00
Inventor 周成合闫聪彦
Owner SOUTHWEST UNIV
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