Abstract
The 2-(3,4,5-trimethoxybenzoyl)-2-aminoindole nucleus was used as the fundamental structure for the synthesis of compounds modified with respect to positions C-4 to C-7 with different moieties (chloro, methyl, or methoxy). Additional structural variations concerned the indole nitrogen, which was alkylated with small alkyl groups such as methyl or ethyl. We have identified 1-methyl-2-(3,4,5-trimethoxybenzoyl)-3-amino-7-methoxyindole as a new highly potent antiproliferative agent that targets tubulin at the colchicine binding site and leads to apoptotic cell death.
MeSH terms
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Animals
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Antimitotic Agents / chemical synthesis*
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Antimitotic Agents / chemistry
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Antimitotic Agents / pharmacology
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Binding Sites
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Biopolymers
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Cell Line, Tumor
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Colchicine / chemistry
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Drug Screening Assays, Antitumor
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Humans
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Indoles / chemical synthesis*
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Indoles / chemistry
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Indoles / pharmacology
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Mice
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Models, Molecular
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Protein Binding
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Structure-Activity Relationship
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Tubulin / chemistry
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Tubulin Modulators / chemical synthesis
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Tubulin Modulators / chemistry
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Tubulin Modulators / pharmacology
Substances
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1-methyl-2-(3',4',5'-trimethoxybenozyl)-3-amino-7-methoxyindole
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Antimitotic Agents
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Biopolymers
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Indoles
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Tubulin
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Tubulin Modulators
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Colchicine