Novel rhodanine derivatives, method for preparing same, and pahrmaceutical composition for the prevention or treatment of aids containing the rhodanine derivatives as active ingredients

A method for preparing a rhodanine derivative, comprising:

• reacting an amine compound of Chemical Formula 2 with carbon disulfide (CS2) and bromoacetic acid to synthesize a compound of Chemical Formula 3,
• reacting a halide compound of Chemical Formula 4 with 5-formyl-2-furanboronic acid to synthesize a compound of Chemical Formula 5, and
• reacting the compound of Chemical Formula 3 synthesized in step 1), with the compound of Chemical Formula 5 synthesized in step 2), to synthesize a compound of Chemical Formula 1, as illustrated in the following Schematic Scheme 1:
• wherein,
• R1 is H, ethyl, cyclohexyl, —(CH2)n-A-B, —(CH2)m-phenyl, 2,4-dimethylphenyl,
• Wherein
• A is (C═O) or SO2,
• B is methyl or hydroxy,
• Z is F, I, NO2, CF3, or —N(CH2CH3)2,
• n is an integer of 1˜3, and
• m is an integer of 1 or 2,
• R2, and R3, which may be the same or different, are independently H, NO2, Br, Cl, methyl, methoxy, ethoxy, —(C═O)—O—CH(CH3)2, or morpholine, or R2 and R3 are positioned ortho to each other, joining together to form
• and
• X is a halogen atom.

A method of preventing or treating AIDS in a subject comprising:

• ingredient
• administering to the subject in need of such prevention or treatment a rhodanine derivative selected from the group consisting of:
• 3-(2,4-dimethyl-phenyl)-5-[5-(3-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 5-[5-(4-morpholin-4-yl-3-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 5-[5-(4-oxo-2-thioxo-thiazolidin-5-ylidene methyl]-furan-2-yl]-isoindole-1,3-dione,
• 3-(2-methanesulfonyl-ethyl)-5-[5-(3-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 5-[5-(4-bromo-phenyl)-furan-2-ylmethylene]-3-(3-oxo-butyl)-2-thioxo-thiazolidin-4-one,
• 5-[5-(4-nitro-phenyl)-furan-2-ylmethylene]-3-(tetrahydrofuran-2-ylmethyl)-2-thioxo-thiazolidin-4-one,
• 3-(4-diethylamino-phenyl)-5-[5-(4-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 5-[5-(2,4-dichloro-phenyl)-furan-2-ylmethylene]-3-(3-fluoro-phenyl)-2-thioxo-thiazolidin-4-one,
• 3-phenethyl-5-(5-phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one,
• 5-[5-(3-chloro-4-methyl-phenyl)-furan-2-ylmethylene]-3-ethyl-2-thioxo-thiazolidin-4-one,
• 5-(naphthalen-1-yl-furan-2-ylmethylene)-3-(2-oxo-propyl)-2-thioxo-thiazolidin-4-one,
• 3-cyclohexyl-5-[5-(2-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 3-(3-fluoro-phenyl)-5-[5-(4-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 3-(1,1-dioxo-tetrahydro-thiopen-3-yl)-5-[5-(2-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 5-[5-(2-nitro-phenyl)-furan-2-ylmethylene]-3-(4-oxo-pentyl)-2-thioxo-thiazolidin-4-one,
• 5-[5-(2-bromo-5-nitro-phenyl)-furan-2-ylmethylene]-3-(4-iodo-phenyl)-2-thioxo-thiazolidin-4-one,
• 5-[5-(2-chloro-4-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-3-(3-trifluoromethyl-phenyl)-thiazolidin-4-one,
• 3-benzyl-5-[5-(4-ethoxy-2-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• {5-[5-(2-methyl-5-nitro-phenyl)-furan-2-ylmethylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid,
• {5-[5-(4-ethoxy-2-nitro-phenyl)-furan-2-ylmethylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid,
• {5-[5-(4-methoxy-2-nitro-phenyl)-furan-2-ylmethylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid,
• 3-(4-nitro-phenyl)-5-[5-(4-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 4-[5-(4-oxo-2-thioxo-thiazolidin-5-ylidene methyl)-furan-2-yl]-benzoic acid isopropylester,
• 5-[5-(2,5-dichloro-phenyl)-furan-2-ylmethylene]-3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-thioxo-thiazolidin-4-one,
• 5-[5-(1 oxo-1,3-dihydro-isobenzofuran-5-yl)-furan-2-ylmethylene-2-thioxo-thiazolidin-4-one,
• 3 furan-2-ylmethyl-5-[5-(2-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 5-[5-(2-nitro-phenyl)-furan-2-ylmethylene]-3-phenethyl-2-thioxo-thiazolidin-4-one,
• 3-(3-chloro-phenyl)-5-[5-(2,3-dichloro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 2-chloro-5-[5-(4-oxo-2-thioxo-thiazolidin-5-ylidene methyl)-furan-2-yl]-benzoic acid propyl ester,
• 4-{5-[5-(3,4-dichloro-phenyl)-furan-2-ylmethylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-butyric acid,
• 2-{5-[5-(4-nitro-phenyl)-furan-2-ylmethylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-succinic acid,
• 5-[5-(4-chloro-phenyl)-furan-2-ylmethylene]-3-furan-2-ylmethyl-2-thioxo-thiazolidin-4-one,
• 5-[5-(2,4-dichloro-phenyl)-furan-2-ylmethylene]-2-thioxo-3-(3-trifluoromethyl-phenyl)-thiazolidin-4-one,
• 3-furan-2-ylmethyl-5-[5-(4-nitro-phenyl)-furan-2-ylmethylene]-2-thioxo-thiazolidin-4-one,
• 3-{5-[5-(3-nitro-phenyl)-furan-2-ylmethylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-propionic acid,
• 3-{5-[5-(4-chloro-phenyl)-furan-2-ylmethylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-propionic acid,
• 4-{5-[3-(2,4-dimethyl-phenyl)-4-oxo-2-thioxo-thiazolidin-5-ylidene methyl]-furan-2-yl}-benzoic acid, and
• {5-[5-(3-nitro-phenyl)-furan-2-ylmethylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid, or
• a pharmaceutically acceptable salt of any of the foregoing compounds.