Fig. 2

Structures of monocarbonyl analogs of curcumin (MACs). A. General structures of MACs (I-IV) containing a 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore (I - “acetone”, II - cyclopentanone, III - cyclohexanone, IV − 4-piperidone), Ar = aryl, R = H, alkyl, aryl). B. In vitro reaction between MAC and glutathione (GSH) in acetonitrile/water, yielding a monoglutathione- and bisglutathione-adduct (Va: Y = N-H, Z = C-F, (3E,5E)-3,5-bis[(2-fluorophenyl)methylene]piperidin-4-one; Vb: Y = N-H, Z = N, (3E,5E)-3,5-bis(2-pyridylmethylene)piperidin-4-one). C. General structure of a symmetric MAC − (2E,6E)-2,6-bis(2-X-benzylidene)cyclohexanone (VIII), and the structure of (2E,6E)-2,6- bis[(trifluoromethyl)benzylidene)cyclohexanone (C66) (IX)