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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Ammonium Compounds
Derivatives
Structure-Activity Relationship
Salts
Water
topovale
imidazole
12-aza-5H-8,9-dimethoxy-5-(2-(N,N-dimethylamino)ethyl)-2,3-methylenedioxydibenzo(c,h)(1,6)naphthyridin-6-one

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

Cite this

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title = "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",
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.",
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",
author = "Wei Feng and Mavurapu Satyanarayana and Tsai, {Yuan chin} and Liu, {Angela A.} and Liu, {Leroy F.} and LaVoie, {Edmond J.}",
year = "2008",
month = "6",
day = "15",
doi = "10.1016/j.bmcl.2008.05.005",
language = "English",
volume = "18",
pages = "3570--3572",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Ireland Ltd",
number = "12",

}

TY - JOUR

T1 - 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

AU - Feng, Wei

AU - Satyanarayana, Mavurapu

AU - Tsai, Yuan chin

AU - Liu, Angela A.

AU - Liu, Leroy F.

AU - LaVoie, Edmond J.

PY - 2008/6/15

Y1 - 2008/6/15

N2 - 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.

AB - 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.

KW - Antitumor

KW - ARC-111

KW - ARC-31

KW - Cytotoxicity

KW - Dibenzo[c,h][1,6]naphthyridin-6-ones

KW - Isoquino[4,3-c]cinnoline-12-ones

KW - Quaternary ammonium salts

KW - Topoisomerase I

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U2 - 10.1016/j.bmcl.2008.05.005

DO - 10.1016/j.bmcl.2008.05.005

M3 - Article

VL - 18

SP - 3570

EP - 3572

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 12

ER -