4-Arylthia(selenium)azole compounds and their uses
A technology of aryl selenazoles and aryl thiazoles, applied in the field of medicine
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Embodiment 1
[0250] Example 1: Preparation of (4-phenyl-1,3-selenazol-2-yl)(3,4,5-trimethoxyphenyl)methanone (compound 1)
[0251] Dissolve 4-phenyl-2-(3,4,5-trimethoxybenzyl)-1,3-selenazole (0.500g, 1.287mmol) in 10ml of acetonitrile, add peroxy tert-butanol (0.464 g, 5.150mmol), iodine (0.033g, 0.129mmol) and pyridine (0.010g, 0.129mmol), reflux for 12 hours. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated to dryness under reduced pressure, and compound 1 was obtained by separation and purification by column chromatography with a yield of 80.2%. 1 H-NMR (300MHz, CDCl 3 )δ3.97(3H,s),3.99(6H,s),7.38(1H,m),7.45(2H,m),7.97(2H,m),8.09(2H,s),8.55(1H,s );MS(ESI):[M+H] + =404.0,[M+Na] + =426.0.
Embodiment 2
[0252] Example 2: Preparation of (4-phenyl-1,3-selenazol-2-yl)(3,4,5-trimethoxyphenyl)methanol (compound 2)
[0253] Compound 1 (0.040g, 0.099mmol) was dissolved in anhydrous methanol, sodium borohydride (0.004g, 0.109mmol) was added, and reacted at room temperature for 1 hour. After the reaction was completed, the solvent was distilled off, an appropriate amount of water was added, the pH was adjusted to acidic with dilute hydrochloric acid, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated to dryness under reduced pressure, and compound 2 was obtained by separation and purification by thin-layer chromatography with a yield of 90.1%. 1 H-NMR (300MHz, CDCl 3 )δ3.83(9H,s),5.90(1H,s),6.76(2H,s),7.36(3H,m),7.86(2H,d),8.06(1H,s); MS(ESI): [M+H] + =406.0.
Embodiment 3
[0254] Example 3: Preparation of (4-phenyl-1,3-selenazol-2-yl)(3,4,5-trimethoxyphenyl)methanone oxime (compound 3)
[0255] Compound 1 (0.050g, 0.124mmol) was dissolved in absolute ethanol, hydroxylamine hydrochloride (0.086g, 1.240mmol) and 1ml of pyridine were added, and the mixture was refluxed for 10 hours. After the reaction was completed, the reaction solution was poured into water, the pH was adjusted to acidic with dilute hydrochloric acid, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated to dryness under reduced pressure, and compound 3 (Z+E) was obtained by separation and purification by thin-layer chromatography with a yield of 86.5%. 1 H-NMR (300MHz, CDCl 3 )δ3.88(3H,s),3.90(6H,s),3.92(1.5H,s),3.94(3H,s),7.02(1H,s),7.07(2H,s),7.36(1.5H ,m), 7.41(3H,m), 7.84(1H,m), 7.91(2H,m), 8.21(0.5H,s), 8.47(1H,s); MS(ESI):[M-H] - =416.8.
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