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Sulfur-containing heterocyclic chalcone derivatives and their preparation methods and applications
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A technology of cyclochalcone and derivatives, applied in the field of medicinal chemistry, to achieve the effect of strong inhibition of activity
Active Publication Date: 2017-06-30
ZHENGZHOU UNIV
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Through splicing principle, a series of sulfur-containing heterocyclic chalcone derivatives were synthesized and screened for their antibacterial activity, but there is no relevant literature report so far
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Embodiment 1
[0023] The preparation of embodiment 1 compound (III)
[0024] Mix 4-hydroxyacetophenone (6.8g, 50mmol) and anhydrous potassium carbonate (13.8g, 100mmol), add 30mL of acetone, stir at room temperature for half an hour, add 1,3-dibromopropane (75mmol ), the temperature was raised to 60°C, and the reaction was continued. TLC monitors the reaction process. After the reaction is over, add distilled water to the system to quench the reaction, then extract 6 times with ethyl acetate, then back-extract the ethyl acetate phase with saturated brine 3 times, 10 mL each time, and finally the organic phase After drying with anhydrous magnesium sulfate, the magnesium sulfate was filtered off, and the filtrate was distilled off under reduced pressure to remove ethyl acetate. The obtained crude product was separated and purified by silica gel column chromatography, eluting with petroleum ether / ethyl acetate=10:1 to obtain compound (III).
Embodiment 2
[0025] The preparation of embodiment 2 general formula (Ⅳ)
[0026] The mercapto-substituted heterocycle (3 mmol) and anhydrous potassium carbonate (4.5 mmol) were stirred in 30 mL of acetone, and compound (III) (0.3 mmol) was added to the system at the same time, and reacted at room temperature. The progress of the reaction was monitored by TLC, and the reaction was complete in about 2 hours. Potassium carbonate was directly removed by suction filtration, and acetone was distilled off the filtrate under reduced pressure to obtain the product without further purification.
Embodiment 3
[0027] The preparation of embodiment 3 general formula (I)
[0028] Add sulfur-containing heterocyclic benzaldehyde (IV) (5 mmol) and the corresponding substituted acetophenone (6 mmol), then add 30 mL of ethanol to dissolve, finally add solid sodium hydroxide (7.5 mmol) and about 3 mL of distilled water, and stir overnight at room temperature. A large amount of solids precipitated, filtered the system, washed 2-3 times with cold ethanol to remove soluble matter, and then washed with distilled water to remove inorganic salts, and the obtained solid was recrystallized with ethanol to obtain crystalline chalcone solid.
[0029] Ⅰ-1: Pale yellow solid, the total yield is 78%; m.p.: 106-108℃. 1 H NMR (400MHz, CDCl 3 ): δ8.02(d, J=8.8Hz, 2H), 7.83(d, J=8.1Hz, 1H), 7.75(d, J=8.4Hz, 1H), 7.72(d, J=16.0Hz, 1H ),7.42(d,J=15.6Hz,1H),7.41(t,J=7.7Hz,1H),7.29(t,J=7.6Hz,1H),6.99(d,J=8.8Hz,2H), 6.87(s,2H),4.23(t,J=5.9Hz,2H),3.94(s,6H),3.90(s,3H),3.57(t,J=6.9Hz,2H),2.39(m,2H ).
[0030] ...
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Abstract
The invention discloses sulfur-containing heterocyclic chalcone derivatives, a preparation method and applications, and belongs to the pharmaceutical chemistry field. Sulfur heterocycle and the chalcone mother nucleus framework are spliced by utilization of a classic nucleophilic reaction, the method is simple and efficient, and sulfur-containing heterocyclic chalcone derivatives are synthesized in a green and environmental protection manner. The structural general formula is shown in the specification, wherein R1 is 2-benzothiazolyl, 2-thiazolinyl, 2-thiadiazoleyl and 2-pyrimidinyl, R2 is 3,4,5-trimethoxy or fluorine, or single substitution or double substitution of chlorine and bromine in different positions of a phenyl ring. In vitro antibacterial activity tests show that the compounds have certain inhibitory activity to staphylococcus aureus, escherichia coli, stenotrophomonas maltophilia and monilia albicans, especially has strong inhibitory activity to escherichia coli, can be employed as candidates or lead compounds for further development, and are applied for application of antibacterial agents.
Description
technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of novel sulfur-containing heterocyclic chalcone derivatives, their preparation methods and their application as a class of novel antibacterial drugs. Background technique [0002] There are a large number of pathogenic harmful bacteria in the living environment, which poses a great threat to human health. Therefore, scientific research workers have been committed to the development of various antibacterial drugs. The basic structure of chalcones is 1,3-diphenylpropenone, which can bind to a variety of receptors and has excellent antibacterial activity. Sulfur-containing heterocycles such as thiazole, benzothiazole, etc. have different degrees of biological effects in terms of insecticidal and bactericidal. Through the principle of splicing, a series of sulfur-containing heterocyclic chalcone derivatives were synthesized and screened for their antibacterial activity, ...
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