Studies on anthracenes. 2. Synthesis and cytotoxic evaluation of 9-acyloxy 1,8-dichloroanthracene derivatives

H. S. Huang, H. F. Chiu, J. M. Hwang, Y. M. Jen, C. W. Tao, K. Y. Lee, Y. L. Lai

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The synthesis and cytotoxic evaluation of 9-acyloxy 1,8-dichloroanthracene derivatives are described. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 1,8-dichloro-9(10H)-anthracenone. Simple acylation of anthracenone occurred with appropriate acyl chlorides in CH 2Cl 2 with a catalytic amount of pyridine to give the 9-acyloxy-1,8-dichloroanthracene derivatives. Considerable interest has developed in the mechanism of how anthracenones achieve this desirable selectivity. These compounds were evaluated in vitro for their ability to inhibit the growth of human oral epidermoid carcinoma cells (KB cell line), human cervical carcinoma cells of ME 180 (GBM 8401) and Chinese hamster ovary (CHO) cells, respectively, as compared to mitoxantrone. The in vitro cytotoxicity evaluation of 9-acyloxy 1,8-dichloroanthracenes against these above cell lines revealed for most of the compounds a cytotoxic potency lower than that of mitoxantrone. The most active compounds were thus selected for further in vitro biological evaluation and structural modification.

Original languageEnglish
Pages (from-to)1346-1348
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume49
Issue number10
DOIs
Publication statusPublished - 2001
Externally publishedYes

Fingerprint

Anthracenes
Mitoxantrone
Cells
Derivatives
KB Cells
Cell Line
Anthraquinones
Acylation
Cricetulus
Chlorides
Squamous Cell Carcinoma
Ovary
Carcinoma
Cytotoxicity
Growth
9-acyloxy 1,8-dichloroanthracene
In Vitro Techniques

Keywords

  • Acylation
  • Anthracene
  • Anthracenedione
  • Anthracenone
  • Peri substituent

ASJC Scopus subject areas

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

Cite this

Studies on anthracenes. 2. Synthesis and cytotoxic evaluation of 9-acyloxy 1,8-dichloroanthracene derivatives. / Huang, H. S.; Chiu, H. F.; Hwang, J. M.; Jen, Y. M.; Tao, C. W.; Lee, K. Y.; Lai, Y. L.

In: Chemical and Pharmaceutical Bulletin, Vol. 49, No. 10, 2001, p. 1346-1348.

Research output: Contribution to journalArticle

Huang, H. S. ; Chiu, H. F. ; Hwang, J. M. ; Jen, Y. M. ; Tao, C. W. ; Lee, K. Y. ; Lai, Y. L. / Studies on anthracenes. 2. Synthesis and cytotoxic evaluation of 9-acyloxy 1,8-dichloroanthracene derivatives. In: Chemical and Pharmaceutical Bulletin. 2001 ; Vol. 49, No. 10. pp. 1346-1348.
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