106115-49-5Relevant articles and documents
Curcumin analogs as potent aldose reductase inhibitors
Du, Zhi-Yun,Bao, Ya-Dan,Liu, Zhong,Qiao, Wei,Ma, Lin,Huang, Zhi-Shu,Gu, Lian-Quan,Chan, Albert S. C.
, p. 123 - 128 (2006)
In the present study, curcuminoids isolated from curcuma longa were demonstrated to possess inhibitory activities on bovine lens aldose reductase. In order to find more potent aldose reductase inhibitor, curcumin analogs were synthesized and evaluated for their ability to inhibit bovine lens aldose reductase enzyme. The results indicated that the compounds with tetrahydroxyl groups, 2,6-bis(3,4-dihydroxybenzylidene)cyclohexanone (A2), 2,5-bis(3,4-dihydroxybenzylidene)cyclopentanone (B2), 1,5-bis(3,4-dihydroxyphenyl)-1,4-pentadiene-3-one (C2), and 3,5-bis(3,4-dihydroxybenzylidene)-4-piperidone (D2) showed remarkably potent inhibitory effects on aldose reductase with IC50 of 2.9 μM, 2.6 μM, 3.4 μM, and 4.9 μM, respectively. The structure-activity relationship revealed that the curcumin analogs with ortho-dihydroxyl groups could form a more tight affinity with aldose reductase to exert more potential inhibitory activities.
Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity
Vatsadze,Gavrilova,Zyuz’kevich,Nuriev,Krut’ko,Moiseeva,Shumyantsev,Vedernikov,Churakov,Kuz’mina,Howard,Gromov
, p. 1761 - 1772 (2017/03/22)
A series of cross-conjugated dienones was synthesized to study the dependence of physicochemical characteristics on the nature of substituents in the aromatic groups of symmetric cyclopentanone dibenzylidene derivatives. The structure of compounds was established by electronic, IR, and NMR spectroscopy and X-ray diffraction study. All the compounds obtained possess the E,E-geometry. In the crystalline state, the arrangement of the dienone molecules is unfavorable for the intermolecular [2+2] photocycloaddition to take place. The low-temperature phases transition for unsubstituted diphenyl derivative of cyclopentanone was detected using variable-temperature X-ray diffraction and differential scanning calorimetry. Oxidation and reduction potentials of the dienones were measured by cyclic voltammetry. Their dependence on the nature and placement of substituents in the benzene rings was demonstrated. A linear correlation (R = 0.9343) between the difference of electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum was found, that allows us to recommend the use of the data obtained in the correlation analysis of other compounds of this class.
Synthesis and evaluation of curcumin-related compounds for anticancer activity
Wei, Xingchuan,Du, Zhi-Yun,Zheng, Xi,Cui, Xiao-Xing,Conney, Allan H.,Zhang, Kun
experimental part, p. 235 - 245 (2012/08/28)
Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3, Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 μM in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity.