Abstract
Phenanthroindolizidines and phenanthroquinolizidines were concisely synthesized by the reductive decyanization of cyano-promoted intramolecular aza-Diels-Alder cycloadducts followed by aryl-aryl coupling. Cyano groups were removed from α-aminoacrylonitriles via treatment with sodium borohydride in 2-propanol in almost quantitative yields; a possible mechanism was proposed and examined using D-labeling experiments. A systematic study of the effects of the phenanthrene substitution pattern on the anticancer activity against three human cancer cell lines was discussed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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2-Propanol / chemistry
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Borohydrides / chemistry
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Catalysis
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Drug Screening Assays, Antitumor
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Humans
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Indolizines / chemical synthesis*
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Indolizines / chemistry
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Molecular Structure
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Phenanthrolines / chemical synthesis*
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Phenanthrolines / chemistry*
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Quinolizines / chemical synthesis
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Quinolizines / chemistry*
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Structure-Activity Relationship
Substances
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Antineoplastic Agents
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Borohydrides
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Indolizines
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Phenanthrolines
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Quinolizines
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phenanthroindolizidine
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phenanthroquinolizidine
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sodium borohydride
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2-Propanol