1-phenyl-3-(4-(pyrimidine-5-ylamino) phenyl) prop-2-ene-1-ketone compound and application thereof
A technology of ketone compounds and compounds, applied in the field of medicinal chemistry, can solve problems such as incurable fatal diseases, and achieve the effects of inhibiting the level of lipid peroxidation, aggregation protection, and inhibiting cell death
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Embodiment 1
[0060] A 1-phenyl-3-(4-(pyrimidin-5-ylamino)phenyl)prop-2-en-1-one compound or a pharmaceutically acceptable salt thereof, a compound of formula (I) ,
[0061]
[0062] Among them, R1, R2, R3 and R4 are hydrogen or hydroxyl respectively, R5 and R6 are containing C 1-16 Alkyl or C 2-16 Alkenyl.
[0063] The present invention provides a pharmaceutical composition, comprising the above compound and a pharmaceutically acceptable carrier or excipient. The present invention can be used alone or made into other clinically available medicines in different dosage forms, and the dosage forms include powder, injection, capsule, pill, microcapsule, tablet, film, soft capsule, ointment, suppository, aerosol, tincture , oral liquid, granules. Medically acceptable pharmaceutical excipients can be added according to pharmaceutical formulations, including fillers, binders, wetting agents, disintegrants, pH regulators or lubricants, etc.
[0064] The application of the compound in the p...
Embodiment 2
[0075] Preparation of (E)-3-(4-((2-(dimethylamino)pyrimidin-5-yl)amino)phenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one The route is as follows:
[0076]
[0077] 1. Preparation of (E)-3-(4-bromophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one (A-C-3)
[0078] Wherein, in step 1 of the present invention, 0.27g (2mmol) 3-hydroxyacetophenone was added into ethanol (20mL) and stirred until completely dissolved, then KOH aqueous solution (10% w / v, 10mL) and 0.44g (2.4 mmol) p-bromobenzaldehyde. The mixture was reacted at room temperature for 72h.
[0079] After the completion of the reaction was detected by TLC, the pH of the reaction mixture was adjusted to 7 with aqueous HCl (10% v / v), washed and extracted with water and ethyl acetate three times, respectively. The crude product obtained by distillation under reduced pressure was purified by silica gel column chromatography using ethyl acetate / petroleum ether (1:10 to 1:3 gradient elution) as eluent to obtain 0.25 g of yellow solid, (...
Embodiment 3
[0091] (E)-1-(3,5-dihydroxyphenyl)-3-(4-((2-(dimethylamino)pyrimidin-5-yl)amino)phenyl)prop-2-ene-1- The preparation route of ketone (A-M-5) is:
[0092]
[0093] 1. Preparation of 1-(3,5-bis(methoxymethoxy)phenyl)ethan-1-one (A-M-1)
[0094] In step one of the preparation method of the present invention, 0.76g (5mmol) 3,5-dihydroxyacetophenone and 1.86g (15mmol) K2CO3 were stirred in anhydrous acetone (50mL) until completely dissolved, and slowly 2.48 g (20 mmol) of bromomethyl methyl ether was added dropwise, the reaction mixture was cooled on an ice bath for 30 min, and then refluxed at 60° C. for 4 h. After the completion of the reaction was detected by TLC, the reaction mixture was cooled to room temperature, washed with water and extracted three times with ethyl acetate, respectively. The crude product obtained by distillation under reduced pressure was purified by silica gel column chromatography using ethyl acetate / petroleum ether (1:5) as eluent to obtain 0.42 g ...
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