Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates

Wei Feng, Mavurapu Satyanarayana, Yuan chin Tsai, Angela A. Liu, Leroy F. Liu, Edmond J. LaVoie

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Several new TOP1-targeting agents were prepared using as intermediates the N,N,N-trimethyl quaternary ammonium salts of either ARC-111 or its 12-aza analog (ARC-31), 3 and 4, respectively. Direct displacement of the quaternary ammonium group with water, imidazole, alkylethylenediamines, or polyhydroxylated alkylamines provides a convenient means for furthering the structure-activity relationships associated with these non-camptothecin TOP1-targeting agents.

Original languageEnglish
Pages (from-to)3570-3572
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume18
Issue number12
DOIs
Publication statusPublished - Jun 15 2008
Externally publishedYes

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Keywords

  • Antitumor
  • ARC-111
  • ARC-31
  • Cytotoxicity
  • Dibenzo[c,h][1,6]naphthyridin-6-ones
  • Isoquino[4,3-c]cinnoline-12-ones
  • Quaternary ammonium salts
  • Topoisomerase I

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

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