Organic Letters · 2016 · 82 citations · 34 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistryStructure-activity RelationshipsMacromolecular Structure DeterminationStructure-activity Relationship AnalysisChemical DerivatizationDerivatizationQuantum Chemical Modeling
Dimericbiscognienyne A (1), an unusual diisoprenyl-cyclohexene-type meroterpenoid dimer, was isolated from Biscogniauxia sp. together with three new monomeric diisoprenyl-cyclohexene-type meroterpenoids (2-4) and one new isoprenyl-benzoic acid-type meroterpenoid (5). All structures were determined by extensive NMR spectroscopic methods, quantum chemical calculations, chemical derivatization, and X-ray crystallography. The formation of 1 is related to a unique intermolecular redox coupling Diels-Alder adduct reaction. Their cytotoxicities and short-term memory enhancement activities against Alzheimer's disease were assessed.
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