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2'-aminochalcone-zole compounds, pyrazoline and cyclopropyl azole derivatives thereof and preparation method and applications of compounds

A technology of cyclopropylazoles and compounds, applied in the field of antimicrobial and antitumor activity, 2'-aminochalconeazole compounds and their pyrazoline and cyclopropylazole derivatives, can solve the problem of α - Problems such as less zoylchalcone compounds

Inactive Publication Date: 2011-05-18
SOUTHWEST UNIVERSITY
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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-zole compounds, pyrazoline and cyclopropyl azole derivatives thereof and preparation method and applications of compounds
  • 2'-aminochalcone-zole compounds, pyrazoline and cyclopropyl azole derivatives thereof and preparation method and applications of compounds
  • 2'-aminochalcone-zole compounds, pyrazoline and cyclopropyl azole derivatives thereof and preparation method and applications of compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1: 2',4'-difluoro-2-(1 H Preparation of -1,2,4-triazol-1-yl)acetophenone (referred to as compound 1)

[0070] Add triazole (6.9 g, 0.1 mol) and potassium carbonate (13.8 g, 0.1 mol) into a 250 mL round bottom flask, take an appropriate amount of acetonitrile as solvent, add 2',4'-difluoro-2-chlorobenzene under stirring Ethyl 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

[0071] Embodiment 2: ( Z )-1-(4-fluoro-2-(piperidin-1-yl)phenyl)-3-phenyl-2-(1 H -1,2,4-triazol-1-yl) prop-2-en-1-one (compound 2 for short) and ( Z )-1-(2,4-bis(piperidin-1-yl)phenyl)-3-phenyl-2-(1 H Preparation of -1,2,4-triazol-1-yl)prop-2-en-1-one (compound 3 for short)

[0072] In a 100 mL single-necked flask, an appropriate amount of toluene was added as a solvent, and 2',4'-difluoro-2-(1 H -1,2,4-triazol-1-yl) acetophenone (2.23 g, 10 mmol), benzaldehyde (1.06 g, 10 mmol) and piperidine (1.87 g, 22 mmol), then add glacial acetic acid 3 Drop it 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 for extraction 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 elu...

Embodiment 3

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

[0076] According to the synthetic method of embodiment 2. The starting material is 2',4'-difluoro-2-(1 H -1,2,4-triazol-1-yl)acetophenone (2.23 g, 10 mmol), benzaldehyde (1.06 g, 10 mmol) and morpholine (1.91 g, 22 mmol) to obtain compound 4 (yellow solid, 2.09 g, yield: 56%, melting point: 123~124°C) and compound 5 (red syrup, 0.84 g, yield: 19%).

[0077] Compound 4: 1 H NMR (300 MHz, CDCl 3 ) δ: 8.11 (s, 1H, trizole 5-H), 8.06 (s, 1H, trizole 3-H), 7.49 ~ 6.70 (m, 9H, C=CH, PhH), 3.77 ~ 3.74 (t, 4H, J = 4.2 Hz, morpholino OCH 2 ), 3.01 ~ 2.98 (t, 4H, J = 4.5 Hz, morpholino NCH 2 ) ppm; MS (m / z): 379 [M+H] + .

[0078] Compound 5: 1 H NMR (300 MHz, CDCl 3 ) δ: 8.11 (s, 1H, trizole 5-H), 8.06 ...

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Abstract

The invention relates to 2'-aminochalcone-zole compounds with structures shown in general formulas (I, II, III, IV and XIII) and pharmaceutically acceptable salts thereof, wherein amine groups are introduced onto chalcone skeletons while the zole-ring displacement of alpha-site can be realized; and the invention also relates to 2'-aminochalcone-zole compound-based pyrazoline derivatives with structures shown in the general formulas (V, VI, VII, VIII, XIV and XV) and pharmaceutically acceptable salts thereof, and relates to 2'-aminochalcone-zole compound-based cyclopropyl zole derivatives with structures shown in general formulas (IX, X, XI, XII, XVI and XVII) and pharmaceutically acceptable salts thereof. The invention relates to the antimicrobial activities and antitumor activities of the 2'-aminochalcone-zole compounds, the pyrazoline derivatives and cyclopropyl zole derivatives and the pharmaceutically acceptable salts. The invention also relates to medical applications of the 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 Applications(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 UNIVERSITY
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