Ant-ligands molecules and biological applications

A compound of Formula (I)

• Wherein
• R1 is
• —(CH2)n—CO—OH;
• —(CH2)n—CO—OR;
• —(CH2)n—OH;
• —(CH2)n— OAr;
• —(CH2)n—C3-C6 cycloalkyl radical;
• —(CH2)2-5-Phenyl or —(CH2)n-Het.;
• —(CH2)n—NH—CO—R;
• —(CH2)n—NH2;
• —(CH2)n—NH—CO—OH;
• —(CH2)n—NH—CO—OR;
• R and R′, in the above radicals, being identical or different and representing H or a C1-C12 alkyl or cycloalkyl radical;
• and Ar is a phenyl or Het., Het. representing an heterocyclic radical with one or several hetero atoms selected between N, S and O, said phenyl or heterocycle being optionally substituted by one or several atoms, groups or radicals selected from Cl, I, F or —CF3;
• one or several —OH, —OR, —COOH or —COOR groups;
• a linear or branched C1-C12 alkyl radical;
• —NH—COR;
• or —CN;
• said groups occupying the same or different positions on the phenyl or heterocyclic radical;
• R2 is
• —(CH2)n— Ar, Ar is a phenyl or Het., Het. representing an heterocyclic radical with one or several hetero atoms selected between N, S and O, said phenyl or heterocycle being optionally substituted by one or several atoms, groups or radicals selected from Br, I, F or —CF3;
• one or several —OH, —OR, —COOH or —COOR groups;
• a phenyl;
• a linear or branched C1-C12 alkyl radical;
• —NH—COR;
• or —CN;
• said groups occupying the same or different positions on the phenyl or heterocyclic radical;
• —(CH2)n—OH;
• —(CH2)n—OR;
• —(CH2)n—CO-Het;
• —(CH2)n—NH—CO—R;
• —(CH2)n—NH2;
• —(CH2)n—CO—OH;
• —(CH2)n—CO—OR;
• R3 forms a phenyl or thienyl group with the two adjacent carbons of the pyrimidinone residue, said phenyl or thienyl being optionally substituted as above defined for Ar;
• and
• n is 0 or an integer from 1 to 5;
• wherein said compounds of Formula (1) are selective for ANT targets.

A method of targeting an ADP/ATP translocator ANT, wherein said method comprises administering an effect amount of an ANT ligand to the target, wherein the ANT ligand comprises a compound of Formula (I):

• Wherein
• R1 is
• —(CH2)n—CO—OH;
• —(CH2)n—CO—OR;
• —(CH2)n—CO—NHR;
• —(CH2)n—CO—N(R, R′);
• —(CH2)n—OH;
• —(CH2)n—OR;
• —(CH2)n—OAr;
• —(CH2)n—C(R,R′)—(CH2)n—OH,
• a linear or branched C4-C12 alkenyl radical;
• —(CH2)n—C3-C6 cycloalkyl radical;
• —(CH2)2-5-Phenyl or —(CH2)n-Het.;
• —(CH2)n—NH—CO—R;
• —(CH2)n—NH2;
• —(CH2)n—N(R,R′);
• —(CH2)n—NH—CO—OH;
• —(CH2)n—NH—CO—OR;
• —NH—(CH2)n—CO—OH;
• —NH—(CH2)n—CO—OR;
• R and R′, in the above radicals, being identical or different and representing H or a C1-C12 alkyl or cycloalkyl radical;
• and Ar is a phenyl or Het, Het. representing an heterocyclic radical with one or several hetero atoms selected between N, S and O, said phenyl or heterocycle being optionally substituted by one or several atoms, groups or radicals selected from halogen atoms Cl, Br, I, F, or halogenated groups CCl3 or —CF3;
• one or several —OH, —OR, —COOH or —COOR groups;
• a phenyl;
• a linear or branched C1-C12 alkyl radical;
• —NH—COR;
• or—CN;
• said groups occupying the same or different positions on the phenyl or heterocyclic radical;
• a linear or branched C1-C12 alkyl radical;
• a linear or branched C4-C12 alkenyl radical;
• —(CH2)n—C3-C6 cycloalkyl radical;
• —(CH2)n Ar or —(CH2)n-Het.;
• —(CH2)n—NH—CO—R;
• —(CH2)n—NH2;
• —(CH2)n—N(R,R′);
• —(CH2)n—NH—CO—OH;
• —(CH2)n—NH—CO—OR;
• —NH—(CH2)n—CO—OH;
• —NH—(CH2)n—CO—OR;
• R2 is
• —(CH2)n—Ar, Ar is a phenyl or Het., Het. representing an heterocyclic radical with one or several hetero atoms selected between N, S and O, said phenyl or heterocycle being optionally substituted by one or several atoms, groups or radicals selected from halogen atoms Br, I, F or halogenated groups —CCl3 or —CF3;
• one or several —OH, —OR, —COOH or —COOR groups;
• a phenyl;
• a linear or branched C1-C12 alkyl radical;
• —NH—COR;
• or—CN;
• said groups occupying the same or different positions on the phenyl or heterocyclic radical;
• a linear or branched C1-C12 alkyl or a linear or branched C2-C12 alkenyl radical;
• —(CH2)n—OH;
• —(CH2)n—OR;
• —(CH2)n—CO-Het;
• —(CH2)n—NH—CO—R;
• —(CH2)n—NH2;
• —(CH2)n—N(R,R′);
• —(CH2)n—CO—OH;
• —(CH2)n—CO—OR;
• a linear or branched C2-C12 alkyl radical;
• —(CH2)n—C(R)═CH—C(R)═CH2,
• R3 forms a phenyl or an heterocyclic condensed thienyl group with the two adjacent carbons of the pyrimidinone residue, said condensed group phenyl or thienyl being optionally substituted as above defined for Ar and Het.;
• and/or condensed to a cyclohexyl or oxanyl group, in turn optionally substituted defined for Ar of R1;
• n is 0 or an integer from 1 to 5.