Phenyloxazole compounds and their application in the preparation of medicines for treating cancer
A phenyloxazole and compound technology, applied in the field of new phenyloxazole compounds, can solve problems such as unclear understanding of protein signal network, failure of clinical development of drugs, no application, etc., and achieve low price, easy storage and transportation. , easy-to-get effects
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Embodiment 1
[0040] The synthetic method one of 5-methyl-2-(4-benzyloxyphenyl)-4 chloromethyl oxazole is as follows:
[0041] Ethyl acetoacetate (10 mmol) was dissolved in NaNO 2 (10mmol) of acetic acid solution (10mL), stirred and cooled to 5-7°C, and carried out nitrosation reaction. After the reaction was completed, diethyl ether (50mL) was added, and the precipitated crystals were collected by filtration, and methanol-diethyl ether was used in a volume ratio of 1: 5 recrystallization again, obtain α-hydroxyimino compound; Then in the acetic acid solution (50mL) saturated with hydrogen chloride gas, α-hydroxyimino compound (5.0mmol) and 4-benzyloxybenzaldehyde (5.0mmol) condensation, Generate an unstable intermediate nitrogen oxide compound; use catalytic hydrogenation to reduce the intermediate nitrogen oxide compound to obtain a compound: ethyl 5-methyl-2-(4-benzyloxyphenyl)-4-oxazole carboxylate; Reduction of compound 5-methyl-2-(4-benzyloxyphenyl)-4-oxazole carboxylic acid ethyl es...
Embodiment 2
[0047] The preparation of embodiment 2 compound (III)
[0048] 2-(4-methoxy-N-(2-(4-benzyloxyphenyl)-5-methyloxazole-4-substituted)methyl)phenylsulfonamide)-3-methylbutanoic acid The synthesis method is as follows:
[0049] Cool anhydrous methanol (100mL) to -10°C, slowly add SOCl with stirring 2 (4mL), after 10 minutes, add L-valine (5.0g, 43mmol), stir at room temperature for 2 days, concentrate under reduced pressure, add anhydrous methanol (2×40mL), repeat concentration twice. Diethyl ether (50 mL) was added, the precipitated crystals were collected by filtration, and recrystallized with methanol-diethyl ether (1:5) to obtain valine methyl ester hydrochloride (6.9 g, 96%), mp 154-155.2°C. Dissolve L-valine methyl ester hydrochloride (5.0g, 30mmol) and p-methoxybenzenesulfonyl chloride (30.0mmol) in anhydrous acetonitrile (100mL), cool to 0°C, and slowly drop into N- Methylmorpholine (2.0 mL), and then stirred at room temperature until the reaction was complete (TLC foll...
Embodiment 3
[0053] Compound (III) 16.55g was obtained according to the method of Example 2, and the same parts as Example 2 were not repeated, the difference was that the residue was obtained by recrystallization [petroleum ether (bp 60-90°C) / acetone] Compound (III): 2-(4-methoxy-N-(2-(4-benzyloxyphenyl)-5-methyloxazole-4-substituted)methyl)phenylsulfonamide)-3 - Methylbutyric acid, yield 90%.
[0054] Dissolve 5 mg of the product in 0.5 mL DMSO to make a 10 mg / mL mother solution, mix well, and use it for subsequent activity tests. Dissolve the remaining product in physiological saline with 2.5% ethanol and 2.5% castor oil, mix it evenly, divide it into injection solutions with a concentration of 5mg / mL / branch and 20mg / mL / branch, put it into a medicine bottle, seal it, and sterilize it to make the product spare.
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