Total Synthesis and Bioactivity of Some Naturally Occurring Pterulones

Gruijters, Bas W. T.; Veldhuizen, A. van; Weijers, C.A.G.M.; Wijnberg, J. B. P. A.

doi:10.1021/np010510m

Cited by 22 publications

(10 citation statements)

References 11 publications

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“…Pterulones 26 and 31 were tested and found to be effective inhibitors of eukaryotic respiration, targeting NADH:ubiquinone oxidoreductase. In accordance, pterulones have potent antifungal activities [24,39].…”

Section: Novel Metabolite Typesmentioning

confidence: 74%

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An Update on Organohalogen Metabolites Produced by Basidiomycetes

Field

Wijnberg

2003

The Handbook of Environmental Chemistry

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Basidiomycetes are an ecologically important group of higher fungi known for their widespread capacity to produce organohalogen metabolites. To date, 100 different organohalogen metabolites (mostly chlorinated) have been identified from strains in 70 genera of Basidiomycetes. This manuscript provides an update of newly discovered chlorinated metabolites described since 1997.Additionally, the biosynthesis, physiological role, environmental fate and significance of Basidiomycete organohalogen metabolites are reviewed. Novel metabolites include chlorinated methoxybenzene azoxyformamide, pterulones (chlorinated 1-benzoxepins), chlorinated anisylpropanoids, tri-and tetrachlorinated phenols. Chlorinated p-anisyl metabolites (CAM) are the most ubiquitous and ecologically significant natural organohalogens produced by higher fungi. Evidence is presented indicating their synthesis from phenylalanine via the phenylpropanoid pathway. They are estimated to be produced at a rate of 300 g ha -1 year -1 in European forests inhabited by the common occurring mushroom, Hypholoma fasciculare. Organohalogen metabolites have several purposeful physiological functions ranging from antibiotic properties, metabolites involved in lignin degradation and synthons for biosynthesis.

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Section: Novel Metabolite Typesmentioning

confidence: 74%

“…Further evidence of antifungal activity of CAM compounds at 50-100 mg L -1 has been reported [13]. New chlorinated compounds with antibiotic activity include the pterulones [24,37,39] and tetrachlorinated catechols [34]. Clearly the antibiotic properties of these metabolites serve to protect the fungal colony from competing microorganisms.…”

Section: Antibioticsmentioning

confidence: 99%

An Update on Organohalogen Metabolites Produced by Basidiomycetes

Field

Wijnberg

2003

The Handbook of Environmental Chemistry

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“…105, 106) [328][329][330][331][332][333][334][335][336][337][338]; (17) synthesis of various ␣,␤-unsaturated oxacyclic ketone derivatives [339]; (18) synthesis of various oxacycles fused to aromatic rings (e.g. 107) [340][341][342][343][344]; (19) synthesis of eight-membered ring cyclic lactones (e.g. 108) [345]; (20) tetraenes [346]; (21) synthesis of a nine-membered ring lactone (e.g.…”

Section: Ring Closing Metathesismentioning

confidence: 99%

The chemistry of the carbon–transition metal double and triple bond: annual survey covering the year 2002

Herndon

2004

Coordination Chemistry Reviews

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“…On the other hand, the seven-membered benzoxepine nucleus can be found in many medicinally relevant natural products and synthetic compounds and represents one of the most profiled chemotypes in modern drug discovery, owing to several pronounced biological activities, such as antitumor and anti-inflammatory properties, attributed to the presence of the benzoxepine unit [21–24]. Last but not least, the benzoxepine nucleus has been of increasing relevance as a synthetic building block for the synthesis of manifold biologically and pharmaceutically important compounds [25–26].…”

Section: Introductionmentioning

confidence: 99%

An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives

Gao¹,

Lin²,

Li³

et al. 2012

Beilstein J. Org. Chem.

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SummaryAn efficient access to the tetracyclic-fused quinoline systems, 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives 4a–l, is described, involving the intramolecular Friedel–Crafts acylation reaction of 2-(phenoxymethyl)-4-phenylquinoline-3-carboxylic acid derivatives 3a–l aided by the treatment with PPA (polyphosphoric acid) or Eaton’s reagent. The required starting compound (2) was obtained by Friedländer reaction of 2-aminobenzophenone (1) with 4-chloroethylacetoacetate by using CAN (cerium ammonium nitrate, 10 mol %) as catalyst at room temperature. The substrates 3a–l were prepared through one-pot reaction of ethyl 2-(chloromethyl)-4-phenylquinoline-3-carboxylate (2) and substituted phenols. Our developed strategy, involving a three-step route, offers easy access to tetracyclic-fused quinoline systems in short reaction times, and the products are obtained in moderate to good yields.

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Total Synthesis and Bioactivity of Some Naturally Occurring Pterulones

Cited by 22 publications

References 11 publications

An Update on Organohalogen Metabolites Produced by Basidiomycetes

An Update on Organohalogen Metabolites Produced by Basidiomycetes

The chemistry of the carbon–transition metal double and triple bond: annual survey covering the year 2002

An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives

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