Studies on anthracenes. 1. Human telomerase inhibition and lipid peroxidation of 9-acyloxy 1,5-dichloroanthracene derivatives

Hsu Shan Huang, Jing M. Hwang, Yee M. Jen, Jing J. Lin, Kung Yuan Lee, Chang Hsin Shi, Hsien Chin Hsu

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25 Citations (Scopus)

Abstract

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 CH2CI2 with catalytic amount of pyridine to give the novel 9-acyloxy 1,5-dichloroanthracene derivatives. Considerable interest 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 membranes. Implications for 9-acyloxy 1,5-dichloroanthracene analogues as potential anticancer agents are discussed.

Original languageEnglish
Pages (from-to)969-973
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume49
Issue number8
DOIs
Publication statusPublished - 2001
Externally publishedYes

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Keywords

  • Acylation
  • Anthracene
  • Anthracenedione
  • Anthracenone
  • Lipid peroxidation
  • peri substituent
  • Telomerase

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

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