1,3-Diarylprop-2-en-1-ones, compositions containing them and use thereof

A product corresponding to formula (I) below:

• 44
• in which:
• a) Y is selected from the group consisting of halogen, C1-C7 linear alkyl, C1-C7 branched alkyl, substituted C1-C7 linear alkyl, substituted C1-C7 branched alkyl, cycloalkyl, substituted cycloalkyl, NH2, NH(R4), N(R4)2, aralkyl, substituted aralkyl, COOH, COO(R4), CONH2, CONH(R4), CON(R4)2, CN, in which R4 represents an optionally substituted C1-C7 alkyl or cycloalkyl group and, when two radicals R4 are present, they may be linked together to form a ring;
• b) Ar2 is selected from the group consisting of:
• 45
• in which:
• 1) when Ar2
• 46
• then one of the radicals R1 and R2 is selected from the group consisting of NH2, NH2.HZ, NHC(O)-amino acid, NH-(GP);
• N=(GP);
• in which the amino acid is preferably serine;
• in which GP is a metabolizable substituent allowing the functional group to be changed:
• NH-(GP)→NH2 or N=(GP)→NH2
• and in which HZ is an organic or mineral acid;
• and
• the other radical R1 or R2 is selected from the group consisting of CH3, C2H5, OCH3, OC2H5, SCH3, NH(R5), N(R5)2, N(R5)(GP), N(R5)C(O)-amino acid, in which R5 represents a C1-C2 alkyl group and, when two radicals R5 are present, they may be linked together to form a ring;
• 2) when Ar2 is
• 47
• then A is a 5- or 6-membered heterocycle, fused to a benzene ring B, said heterocycle A is aromatic or non-aromatic, comprising one or two hetero atoms, at least one of which is a nitrogen atom linked directly to B and bearing a side chain R8, in which R8 is chosen from the group consisting of H, (C1-C3)alkyl, (C1-C3)alkyl-OH, (C1-C3)alkyl-O(C1-C3)alkyl, (C1-C3)alkyl-NH2, (C1-C3)alkyl-NH(R7), (C1-C3)alkyl-N(R7)2,
• 48
• in which R9 is chosen from H, (C1-C3)alkyl, in which each R7 independently represents a (C1-C3)alkyl or (C3-C7) cycloalkyl group, or alternatively, when two radicals R7 are present, they are linked together to form a 5-membered heterocycle;
• c) X is selected from the group consisting of O, NOH, NO(R3), in which R3 is selected from the group consisting of H, C1-C7 linear alkyl, C1-C7 branched alkyl, cycloalkyl, C1-C7 linear haloalkyl, C1-C7 branched haloalkyl, substituted cycloalkyl, halocycloalkyl, aralkyl, substituted aralkyl;
• and
• d) Ar is selected from the group consisting of 2,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,3,5-trimethoxyphenyl, 2,4,5-trimethoxyphenyl, 2,3,4,5-tetramethoxyphenyl, 3-methoxy-4,5-methylenedioxy, 3-methoxy-4,5-ethylenedioxy, 2-methoxy-4,5-methylenedioxy, 2-methoxy-4,5-ethylenedioxy, 2-methoxy-3,4-methylenedioxy and 2-methoxy-3,4-ethylenedioxy radicals.