Synthesis and Biological Properties of Benzo-Annulated Rutaecarpines

A series of benzo-annulated rutaecarpines were prepared from anthranilic acid and 3-aminonaphthalene-2-carboxylic acid by Fischer indole synthesis as key reaction. Cytotoxicity was somewhat increased by the introduction of benzo-annulation, which was not directly related to the inhibitory activity a...

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Bibliographic Details
Published in:Biological & Pharmaceutical Bulletin 2010/10/01, Vol.33(10), pp.1704-1709
Main Authors: Hong, Young Hwan, Lee, Woo Jin, Lee, Seung Ho, Son, Jong Keun, Kim, Hye-Lin, Nam, Jung Min, Kwon, Youngjoo, Jahng, Yurngdong
Format: Article
Language:English
Subjects:
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - pharmacology
Antineoplastic Agents, Phytogenic - therapeutic use
benzorutaecarpine
Cell Line, Tumor
cytotoxicity
DNA Topoisomerases, Type I - metabolism
DNA Topoisomerases, Type II - metabolism
Drug Screening Assays, Antitumor
Fischer indole synthesis
Humans
Indole Alkaloids - chemical synthesis
Indole Alkaloids - pharmacology
Indole Alkaloids - therapeutic use
Neoplasms - drug therapy
Phytotherapy
Plant Extracts - chemical synthesis
Plant Extracts - pharmacology
Plant Extracts - therapeutic use
Quinazolines - chemical synthesis
Quinazolines - pharmacology
Quinazolines - therapeutic use
Rutaceae - chemistry
rutaecarpine
Structure-Activity Relationship
topoisomerase
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Summary:A series of benzo-annulated rutaecarpines were prepared from anthranilic acid and 3-aminonaphthalene-2-carboxylic acid by Fischer indole synthesis as key reaction. Cytotoxicity was somewhat increased by the introduction of benzo-annulation, which was not directly related to the inhibitory activity against topoisomerases (topo) I and II. Benzo-annulation on ring A led to significant increase of inhibitory activity against topo II while annulations on ring E increased inhibitory activity against topo I.
ISSN:0918-6158
1347-5215
DOI:10.1248/bpb.33.1704