3-3-DI-SUBSTITUTED-OXINDOLES AS INHIBITORS OF TRANSLATION INITIATION
First Claim
Patent Images
1. A compound of formula I:
- wherein A is selected from the group consisting of carbocyclic aromatic ring, heterocyclic ring and heteroaromatic ring;
R1 is selected from the group consisting of (halo)alky, (un)substituted (alkyl)aryl, halogen, CN, COOH, alkenyl, alkynyl, alkoxy and cycloalkoxy;
R2 is selected from the group consisting of (un)substituted aryl, (un)substituted heterocyclic, (un)substituted heteroaromatic, Ar—
NHSO2Ar and Ar—
NHCOAr;
R3 is selected from the group consisting of (un)substituted aryl, (un)substituted heterocyclic, (un)substituted heteroaromatic, Ar—
NHSO2Ar and Ar—
NHCOAr;
R4 is selected from the group consisting of (un)substituted aryl, (un)substituted heterocyclic, (un)substituted heteroaromatic, Ar—
NHSO2Ar and Ar—
NHCOAr;
X is selected from the group consisting of unsubstituted or substituted nitrogen, oxygen, sulfur and carbon;
Y is selected from the group consisting of unsubstituted or substituted nitrogen, oxygen and sulfur and carbon; and
n=0-4.
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Abstract
Compositions and methods for inhibiting translation using 3-(5-tert-Butyl-2-Hydroxy-phenyl)-3-phenyl-1,3-dihydro-indol-2-one and/or its derivatives are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using 3-(5-tert-butyl-2-hydroxy-phenyl)-3-phenyl-1,3-dihydro-indol-2-one and/or its derivatives are described.
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Citations
15 Claims
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1. A compound of formula I:
wherein A is selected from the group consisting of carbocyclic aromatic ring, heterocyclic ring and heteroaromatic ring; R1 is selected from the group consisting of (halo)alky, (un)substituted (alkyl)aryl, halogen, CN, COOH, alkenyl, alkynyl, alkoxy and cycloalkoxy; R2 is selected from the group consisting of (un)substituted aryl, (un)substituted heterocyclic, (un)substituted heteroaromatic, Ar—
NHSO2Ar and Ar—
NHCOAr;R3 is selected from the group consisting of (un)substituted aryl, (un)substituted heterocyclic, (un)substituted heteroaromatic, Ar—
NHSO2Ar and Ar—
NHCOAr;R4 is selected from the group consisting of (un)substituted aryl, (un)substituted heterocyclic, (un)substituted heteroaromatic, Ar—
NHSO2Ar and Ar—
NHCOAr;X is selected from the group consisting of unsubstituted or substituted nitrogen, oxygen, sulfur and carbon; Y is selected from the group consisting of unsubstituted or substituted nitrogen, oxygen and sulfur and carbon; and n=0-4.
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2. A compound of formula II:
wherein R1 is selected from the group consisting of H, 5-bromo, 5-chloro, 7-bromo, 5-iodo, 5-OCF3, 5-sulfonic acid, 5-nitro, 4-bromo, 6-bromo, 5-ethyl, 7-ethyl, 4-ethyl, 6-ethyl, 7-iodo, 5-fluoro, 7-COOH, 7-COOMe and 4-Cl; and R2 is selected from the group consisting of 7-formamide-N-[2-(4-amino-phenyl)-ethyl], 7-CO2H, 7-CH2OH, 7-CH2-N-imidazole and H with the proviso that R1 and R2 cannot both be H, and with the further proviso that when R2 is H, R1 cannot be 5-chloro, 5-nitro or 5-fluoro.
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3. A compound of formula III:
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wherein X is selected from the group consisting of oxygen, NH and CH2; and R is selected from the group consisting of 3′
-CH2CH(CO2Me)NH2, 3′
-CH2CH(CO2Me)NHFmoc, 3′
-t-Bu, 3′
-OH, 3′
-O(CH2)3CHCH2, 3′
-O(CH2)4Br, 3′
-O(CH2)4NMe2, 3′
-O(CH2)4N3,3′
-O(CH2)4NH2, 3′
-CF3, 3′
-CH3, 3′
-n-heptyl, 3′
-n-nonyl, 3′
-i-Bu, 3′
-1-propyl, 3′
-n-propyl, 3′
-n-octyl, 3′
-Et, 3′
-n-pentyl, 3′
-n-Bu, 3′
-n-hexyl, 3′
-n-cyclopentyl, 3′
-n-cyclohexyl, 4-NHSO2(4-tBu)Ph and 3′
-NHSO2(4-tBu)Ph.
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4. A compound of formula IV:
wherein R is selected from the group consisting of 4-F, 4-O(CH2)3CHCH2, 3-Cl, 3-F, 3-Me, 2-Me and 2-OMe.
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5. A compound of formula V:
wherein R is selected from the group consisting of —
SO2-Camphor, —
CO(CH2)6CO2H, —
CO(CH2)3CONHOH, —
CH2CH2NHBoc, —
CO(CH2)3CO2H, —
CH2CO2H, —
CH2CO-Leu-Phe-CH2OH and —
CH2CO2Me.
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6. A compound of formula VI:
wherein R1 is selected from the group consisting of 7-Br, 4-Cl, 5-Br, 5-NO2, 5-I, 5-OMe, 5-Cl, 7-CF3, 5-NH2, 4-Br, 6-Br, H, 7-OMe, 7-1,5-Et, 7-Et, 4-Et, 6-Et, 5-F, 5-N3, 7-COOH, 7-CO2H, 4-Cl, 6-Cl and 5-NHSO2-1-napthyl; and R2 is H or 7-CO2H.
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7. A compound of formula VII:
wherein R1 is selected from the group consisting of H, 2-OH, 3-O(CH2)4NMe2, 3-O(CH2)4N3, 3-t-Bu, 2-OMe, 3-OMe, 4-OH, 4-OPh, 4-Ph, 4-NMe2, 4-n-propyl, 4-i-Bu, 4-n-Bu, 4-O(CH2)2OH, 4-OMe, 2-CH2CO2H and 4-t-Bu; and R2 is selected from the group consisting of 2-OH, 4-OH, 4-t-Bu and H with the proviso that R1 and R2 cannot both be H.
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8. A compound of formula VIII:
wherein R1 is selected from the group consisting of H and 7-CO2H; R2 is selected from the group consisting of H, 2-Me, 3′
-Me, 3-F and 3-CF3; andR3 is selected from the group consisting of H, 2-NHFmoc, 2-NHSO2CH2Ph, 2-NHSO2CH3, 2-NHSO2(4-tBu)Ph, 2-NHSO2(4-NHAc)Ph, 2-NHSO2(3-CF3)Ph, 2-NHSO2(4-NO2)Ph, 2-NHSO2(4-OMe)Ph, 2-NHSO2(4-Br)Ph, 2-NHSO2(4-I)Ph, 2-NHSO2(4-Ph)Ph, 2-NHSO2(4-OPh)Ph, 2-NHAc, 2-NHCO(4-tBu)Ph and 3′
-NHSO2(4-tBu)Ph.
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9. A compound of formula IX:
wherein R is selected from the group consisting of —
CH2-(4-Cl)Ph, —
CH2CHCH2, —
CH2OH, —
CH2CO2H, —
CH2OCH2CHCH2, —
SO2(4-O-n-Bu)Ph, —
SO2(4-O-Ph)Ph, —
SO2(4-NHAc)Ph, —
SO2(4-CH2CH2CO2Me)Ph, —
SO2(4-OMe)Ph and —
SO2(4-t-Bu)Ph.
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10. A compound of formula X:
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11. A compound of formula XI:
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12. A compound of formula XII:
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13. A compound of formula XIII:
wherein R is selected from the group consisting of 2-Thiophene, —
(CH2)11CH3, —
CH2Ph, —
CCH, -cyclohexyl and —
C6F5.
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14. A compound of formula XIV:
wherein R is selected from the group consisting of H, 3-Cl, 3-F, 3-Me and 3-t-Bu.
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15. A compound for inhibiting translation, wherein said compound is selected from formulae I-XIV above.
Specification