Abstract
The enantiomeric lactams (-)-8, (+)-8, (+)-9, and (-)-9 were formed by the reaction of the dimeric phthalide rac-tokinolide B (rac-3) with (R)-(+)-α-methylbenzylamine and (S)-(-)-α-methylbenzylamine. The absolute configurations of compounds 8 and 9 were assigned by experimental and theoretically calculated electronic circular dichroism methods for (+)-8 and (-)-9. Compounds 3, 5, (-)-8, (+)-8, (+)-9, and (-)-9 displayed cytotoxic activity toward several human tumor cell lines, with (-)-8 and (-)-9 being the most potent.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Algorithms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Benzofurans / pharmacology
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Circular Dichroism
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Drug Screening Assays, Antitumor
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Humans
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K562 Cells
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Lactams / chemical synthesis*
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Lactams / chemistry
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Lactams / pharmacology
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Models, Theoretical
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Nuclear Magnetic Resonance, Biomolecular
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Phenethylamines / chemical synthesis*
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Phenethylamines / chemistry
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Phenethylamines / pharmacology
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Stereoisomerism
Substances
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Antineoplastic Agents
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Benzofurans
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Lactams
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Phenethylamines
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tokinolide B
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1-phenethylamine