Chalcone derivatives and their use to treat diseases
a technology of chalcone and derivatives, applied in the field of chalcone derivatives and their use to treat diseases, can solve the problems of thrombosis, myocardial infarction and ischemic heart disease, late graft loss, and thrombosis of the transplanted organ
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embodiment 6c
[0620] In a 61st embodiment, the invention is represented by Formula I or its pharmaceutically acceptable salt or ester, wherein:
[0621] R2β, R3β, R4β, R5β, R6β, R2α, R3α, R4α, R5α and R6α are independently selected from the group consisting of hydrogen, halogen, nitro, alkyl, lower alkyl, alkenyl, alkynyl, carbocycle, cycloalkyl, cycloalkylalkyl, haloalkyl, aryl, arylalkyl, heteroaryl, heteroaryl lower alkyl, heterocyclic, heterocyclic lower alkyl, alkylthioalkyl, cycloalkylthioalkyl, arylthio lower alkyl, aralkyl lower thioalkyl, heteroarylthio lower alkyl, heteroaralkyl lower thioalkyl, heterocyclicthio lower alkyl, heterocyclicalkyl lower thioalkyl, lower alkyl S(O)-lower alkyl, lower alkyl-S(O)2-lower alkyl, arylsulfinyl lower alkyl, arylsulfonyl lower alkyl, —C(O)R2, R2C(O)alkyl, aminoalkyl, cycloalkylaminoalkyl, arylamino lower alkyl, heteroarylamino lower alkyl, heterocyclicamino lower alkyl,
[0622] hydroxyl, hydroxyalkyl, alditol, carbohydrate, polyol alkyl, alkoxy, lower a...
example 1
[0844]
1-(2,2-Bis-hydroxymethyl-benzo[1,3]dioxol-5-yl)-3E-3,4-dimethoxy-5-thiophen-2-yl-phenyl)propenone
[0845] Ex-1A: Catechol (2.2 g, 20 mmol) was dissolved in acetone. Diethyl dibromomalonate (7.0 g, 22 mmol) and potassium carbonate (2.76 g) were added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water was added to the residue. The residue was extracted with dichloromethane, and the organic phase was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (hexanes / ethyl acetate, 4:1) gave 3.9 g of benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester. 1H-NMR (CDCl3) δ 6.90-6.97 (m, 4H), 4.37(q, J=7 Hz, 4H), 1.32(t, J=7 Hz, 6H).
[0846] Ex-1B: [Bis(ethoxycarbonyl)methyldenedioxy]benzene obtained from Ex-1A (3.9 g, 14.7 mmol) was dissolved in THF (100 mL) and cooled with ice-water. Lithium aluminum hydride (1 M solution in THF, 44 mL) was added dropwise, and the mixture was stirred overnight. Th...
example 2
[0850]
1-(2,2-Bis-hydroxymethyl-benzo[1,3]dioxol-5-yl)-3E-(4-thiophen-2-yl-phenyl)-propenone
[0851] Ex-2A: 4-(Thien-2-yl)benzaldehyde was obtained in a similar manner as described in Ex-1D from 4-bromobenzaldehyde. 1H-NMR (CDCl3) δ 10.00 (s, 1H), 7.88 (d, J=9 Hz, 2H), 7.77 (d, J=9 Hz, 2H), 7.46 (d, J=4 Hz, 1H), 7.39-7.41 (m, 1H), 7.12-7.15 (m, 1H).
[0852] The title compound was obtained when 5-acetyl-benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester from Ex-1C was condensed with 4-(Thien-2-yl)benzaldehyde from Ex-2A in a similar manner as described in Ex-1. Yellow solid, mp 166-168° C., 23.6% yield. 1H-NMR (CDCl3) δ 7.77 (d, J=15 Hz, 1H), 7.60-7.65 (m, 5H), 7.51 (d, J=2 Hz, 1H), 7.45 (d, J=15 Hz, 1H), 7.37-7.38 (m, 1H), 7.32(d, J=5 Hz, 1H), 7.09 (dd, J=4, 5 Hz, 1H), 6.88 (d, J=8 Hz, 1H), 3.96 (d, J=7 Hz, 4H). MS m / z=394 ([M]+, 50%), 363 (100%). HRMS (EI) Calcd. for C22H18O5S: 394.0875. Found: 394.0869.
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