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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.
- 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.
- Subjects :
- Animals
Antineoplastic Agents chemistry
Antineoplastic Agents pharmacology
Cell Line, Tumor
Cell Proliferation drug effects
Dose-Response Relationship, Drug
Humans
Hydrophobic and Hydrophilic Interactions
Mice
Molecular Structure
Naphthyridines chemistry
Naphthyridines pharmacology
Stereoisomerism
Structure-Activity Relationship
Xenograft Model Antitumor Assays
Antineoplastic Agents chemical synthesis
DNA Topoisomerases, Type I drug effects
Naphthyridines chemical synthesis
Quaternary Ammonium Compounds chemistry
Subjects
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