Substituted imidazole-1-ethylene compound and application thereof
A compound and ethylene-based technology, applied in the fields of medicinal chemistry and pharmacotherapeutics, can solve the problems of narrow anti-bacterial spectrum of antimetabolites, insufficient deep fungal infection, complex structure, etc.
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Embodiment 1
[0049] Preparation of 2-bromo-1-acetophenone (II-1)
[0050]
[0051] Dissolve 2.365 grams of acetophenone in 35 milliliters of glacial acetic acid, drop by drop into 1.2 milliliters of bromine dissolved in 15 milliliters of glacial acetic acid solution, and react under 250W tungsten light. After the reaction, the solvent was distilled off under reduced pressure, washed with water, extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated and separated by column chromatography (ethyl acetate / petroleum ether=1 / 60, v / v) , to obtain intermediate II-12.478 g, which is a white flaky solid, and the yield is 72%.
[0052] 1 H NMR (400MHz, CDCl 3 ): δ7.99(d, J=7.7Hz, 2H), 7.62(t, J=7.4Hz, 1H), 7.50(t, J=7.7Hz, 2H), 4.47(s, 2H).
Embodiment 2
[0054] Preparation of 2-(1H-imidazol-1-yl)-1-acetophenone (III-1)
[0055]
[0056] 594 mg of II-1 was dissolved in 10 ml of anhydrous tetrahydrofuran, and 245 mg of imidazole and 420 μl of triethylamine were added in sequence, under nitrogen protection, and reacted overnight at room temperature. After the reaction, suction filtration, the filtrate was concentrated and then separated by column chromatography (methanol / dichloromethane=1 / 30, v / v) to obtain Intermediate III-1335 mg as a light yellow solid with a yield of 60%.
[0057] 1 H NMR (400MHz, CDCl 3 ):δ7.99(d,J=7.8Hz,2H),7.67(t,J=7.4Hz,1H),7.62–7.50(m,3H),7.16(s,1H),6.97(s,1H) ,5.43(s,2H).
Embodiment 3
[0059] (2Z,4E)-1-phenyl-2-(1H-imidazol-1-yl)-5-(2,4-dichlorophenyl)-penta-2,4-dien-1-one (IA -1) Preparation
[0060]
[0061] Dissolve 271 mg of III-1 in 3 ml of toluene, add 224 mg of (E)-3-(2,4-dichlorophenyl)acrolein, 55 microliters of piperidine and 12 microliters of glacial acetic acid in sequence, and nitrogen protection Reaction at 75°C for 4h. After the reaction, cool to room temperature, evaporate the solvent under reduced pressure, and separate the residue by column chromatography (ethyl acetate:petroleum ether:triethylamine=1:2:0.15, v / v / v) to obtain a crude product. The resulting crude product was recrystallized at 75°C (solvent: ethyl acetate / petroleum ether = 1 / 70, v / v), and filtered to obtain 55 mg of the title compound as a light yellow solid with a yield of 9.9%.
[0062] 1 H NMR(400MHz,MeOD):δ7.87(s,1H),7.81(d,J=7.4Hz,2H),7.68(t,J=7.5Hz,1H),7.63–7.52(m,5H), 7.49 (d, J=11.1Hz, 1H), 7.34 (d, J=13.2Hz, 2H), 7.20 (s, 1H), 6.84 (dd, J=15.5, 11.1Hz, 1H). MS...
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