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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.

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.

Authors :
Feng W
Satyanarayana M
Tsai YC
Liu AA
Liu LF
Lavoie EJ
Source :
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2008 Jun 15; Vol. 18 (12), pp. 3570-2. Date of Electronic Publication: 2008 May 06.
Publication Year :
2008

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.

Details

Language :
English
ISSN :
1464-3405
Volume :
18
Issue :
12
Database :
MEDLINE
Journal :
Bioorganic & medicinal chemistry letters
Publication Type :
Academic Journal
Accession number :
18511275
Full Text :
https://doi.org/10.1016/j.bmcl.2008.05.005