Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Antineoplastic Agents, Phytogenic / pharmacology*
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Antineoplastic Agents, Phytogenic / therapeutic use
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Cell Line, Tumor
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DNA Topoisomerases, Type I / metabolism
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DNA Topoisomerases, Type II / metabolism
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Drug Screening Assays, Antitumor
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Humans
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Indole Alkaloids / chemical synthesis*
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Indole Alkaloids / pharmacology*
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Indole Alkaloids / therapeutic use
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Neoplasms / drug therapy
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Phytotherapy
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Plant Extracts / chemical synthesis*
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Plant Extracts / pharmacology*
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Plant Extracts / therapeutic use
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Quinazolines / chemical synthesis*
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Quinazolines / pharmacology*
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Quinazolines / therapeutic use
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Rutaceae / chemistry*
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Structure-Activity Relationship
Substances
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Antineoplastic Agents, Phytogenic
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Indole Alkaloids
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Plant Extracts
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Quinazolines
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rutecarpine
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DNA Topoisomerases, Type I
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DNA Topoisomerases, Type II