Curcumin analogs with anti-tumor and anti-angiogenic properties

A compound selected from the group consisting of:

• 1,5-Bis-(2,4-difluorophenyl)penta-1,4-diene-3-one;
• 3,5-Bis-(2-fluorobenzylidene)-piperidin-4-one-acetate;
• and
• 3,5-Bis-(2-hydroxybenzylidene)tetrahydro-4-H-pyran-4-one.

A method of treating cancerous tissue in a subject, comprising administering to the subject an effective amount of a compound of formula (I)

• 43
• wherein:
• Y is OH, halogen, or CF3;
• Z is H, OH, OR1, halogen, or CF3;
• X1 and X2 are independently C or N;
• and
• A is selected from the group consisting of:
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• wherein n is 1-8;
• X3 is O, S, SO, SO2, NH, or NR1;
• Q is NH or NR1;
• and V1-4 are each independently OH, OR2, or halogen;
• R1 and R2 are independently H, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycle, substituted heterocycle, acyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl;
• the dashed lines indicate the presence of optional double bonds;
• and L is the point of bonding of A to the compound structure, with the proviso that Z is not H when Y is OH, Cl or Br and A is
• 45
• and pharmaceutically acceptable salts thereof.

A method of treating cancerous tissue in a subject, comprising administering to the subject an effective amount of a compound of formula (II)

• 46
• wherein:
• X4 is (CH2)m, O, S, SO, SO2, or NR12, where R12 is H, alkyl, substituted alkyl, acyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl;
• m is 1-7;
• each X5 is independently N or C—R11;
• and R3-R11 are independently H, halogen, hydroxyl, alkoxy, CF3, alkyl, substituted alkyl, alkenyl, alkynyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, alkaryl, arylalkyl, heteroaryl, substituted heteroaryl, heterocycle, substituted heterocycle, amino, alkylamino, dialkylamino, carboxylic acid, carboxylic ester, carboxamide, nitro, cyano, azide, alkylcarbonyl, acyl, or trialkylammonium;
• and
• the dashed lines indicate optional double bonds;
• with the proviso that when X4 is (CH2)m, m is 2-6, and each X5 is C—R11, R3-R11 are not alkoxy, and when X4 is NR12 and each X5 is N, R3-R10 are not alkoxy, alkyl, substituted alkyl, alkenyl, alkynyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, alkaryl, arylalkyl, heteroaryl, substituted heteroaryl, amino, alkylamino, dialkylamino, carboxylic acid, or alkylcarbonyl.