Synthesis of benzo-annulated tryptanthrins and their biological properties

Jing Lu Liang, So Eun Park, Youngjoo Kwon, Yurngdong Jahng

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

A series of benzo-annulated derivatives of tryptanthrin were prepared and their optical and redox properties were studied. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with an increase of activity on topo II by benzo-annulation on quinazolin-4(3H)-one moiety. Although the benzo-annulation on quinazolin-4(3H)-one ring did not affect significantly on the inhibitory activities against topo I and II, the benzoannulation on indolin-3-one ring affected the inhibitory activity very much especially by linear annulation. Cytotoxicities were not significantly changed upon benzoannulation, which were not directly related either to the inhibitory activities against topo I and II or to the reduction potentials.

Original languageEnglish
Pages (from-to)4962-4967
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume20
Issue number16
DOIs
StatePublished - 15 Aug 2012

Bibliographical note

Funding Information:
Financial support from Korean Science Foundation (KRF-2008-521-E00189) and Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2010-0002646) are gratefully acknowledged.

Keywords

  • 3-Amino-2-naphthoic acid
  • Benzotryptanthrin
  • Cytotoxicity
  • Isatin
  • Isatoic anhydride
  • Topoisomerase I
  • Topoisomerase II
  • Tryptanthrin

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