Studies on Anthracenes. 1. Human Telomerase Inhibition and Lipid Peroxidation of 9-Acyloxy 1, 5-Dichloroanthracene Derivatives

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The synthetically useful approaches to 9-acyloxy 1, 5-dichloroanthracene derivatives are reported. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 1, 5-dichloro-9(10H)-anthracenone. Simple regioselective acylation of anthracenone is applied with appropriate acyl chlorides in CH_2Cl_2 with catalytic amount of pyridine to give the novel 9-acyloxy 1, 5-dishloroanthracene derivatives. Considerable interst has developed in the mechanism of how anthracenone achieves this desirable selectivity. In an attempt to understand the mechanism of this reaction, solid-state structures of anthracene derivatives have been obtained. In addition, the inhibition of lipid peroxidation in model membranes was determined as was their ability to inhibit the telomere-addition function of the human telomerase enzyme together with their inhibition of the Taq polymerase enzyme. In contrast to(+)-α-tocopherol, 3b, 3c, 3d, 3g and 3i do not enhance lipid peroxidation in model membrances. Implications for 9-acyloxy 1, 5-dichloroanthracene analogues as potential anticancer agents are discussed.
公益社団法人日本薬学会の論文
2001-08-01