Abstract
A novel harringtonolide-inspired scaffold containing a cycloheptatriene ring and two fused cyclopentane rings has been synthesised from simple starting materials. The scaffold, containing a similar substitution pattern and relative stereochemistry to the complex diterpenoid, has been enumerated into a small library of derivatives. One of these library members has been converted into a sub-library of substituted triazoles using copper-catalysed azide-alkyne cycloaddition (click) chemistry. The scaffold may be useful in drug discovery or in the preparation of additional molecular probes for chemical biology.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents, Phytogenic / analysis
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Azides / chemistry
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Catalysis
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Chemistry, Pharmaceutical*
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Click Chemistry
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Copper / chemistry
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Cyclopentanes / chemistry
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Drug Discovery
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Harringtonines / analysis
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Harringtonines / chemical synthesis*
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Magnetic Resonance Spectroscopy
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Models, Molecular
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Molecular Probes / analysis
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Molecular Probes / chemical synthesis*
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Neoplasms / drug therapy
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Plants, Medicinal / chemistry
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Small Molecule Libraries / analysis
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Small Molecule Libraries / chemical synthesis*
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Stereoisomerism
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Taxaceae / chemistry*
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Triazoles / analysis
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Triazoles / chemical synthesis*
Substances
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Antineoplastic Agents, Phytogenic
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Azides
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Cyclopentanes
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Harringtonines
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Molecular Probes
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Small Molecule Libraries
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Triazoles
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Copper