- First total synthesis of chromanone A, preparation of related compounds and evaluation of their antifungal activity againstCandida albicans, a biofilm forming agent
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A straightforward and convenient approach for the first total syntheses of chromanone A and a related 7-OMe substituted natural product is reported. These unique C-3 substituted 2-hydroxymethyl chromones were recently isolated as fungal metabolites. Chromanone A was synthesized in 25.3% overall yield from the readily available pyrocatechol, whereas the second natural product was prepared in 39.7% global yield. A small library of chromones, including both natural products and some of their synthetic heterocyclic precursors, was evaluated againstCandida albicansATCC 10231, a biofilm forming agent. It was found that 8-methoxy-3-methyl-4-oxo-4H-chromene-2-carbaldehyde, a partially oxidized form of chromanone A, exhibited a minimum inhibitory concentration of 7.8 μg mL?1and significantly inhibited the yeast's virulence factors, including the adherence to buccal epithelial cells and the secretion of phospholipases, as well as the formation of germ tubes and the generation of the hyphal pseudomycelium. In addition, despite the heterocycle exhibiting non-significant inhibition of the formation of theCandidabiofilm, it completely inhibited the growth ofC. albicansin preformed biofilms at 62.5 μg mL?1
- Bracca, Andrea B. J.,Cordisco, Estefanía,Cortés, Iván,Kaufman, Teodoro S.,Sortino, Maximiliano A.,Svetaz, Laura A.
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- Bifunctional Amine-Squaramide Catalyzed Friedel–Crafts Alkylation Based on ortho-Quinone Methides in Oil-Water Phases: Enantioselective Synthesis of Triarylmethanes
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An efficient enantioselective Friedel–Crafts alkylation reaction of electron-rich β-naphthol with in situ generated ortho-quinone methides catalyzed by chiral bifunctional amine-squaramide catalysts has been developed. The chiral triarylmethane derivative
- Wang, Yifeng,Zhang, Cheng,Wang, Haojiang,Jiang, Yidong,Du, Xiaohua,Xu, Danqian
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supporting information
p. 791 - 797
(2017/03/11)
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- Synthesis of Side-Chain-Modified Analogues of the Allergen Primin
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Benzoquinones such as primin (2-methoxy-6-pentyl-1,4-benzoquinone) from Primula obconica HANCE (Primulaceae) are known to be strong sensitizers and thus the source of severe allergic contact dermatitis (cell-mediated type of allergy).In order to determine
- Koenig, Wilfried A.,Faasch, Holger,Heitsch, Holger,Colberg, Cornelia,Hausen, Bjoern M.
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p. 387 - 393
(2007/10/02)
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- Tobacco smoke chemistry. 2. Alkyl and alkenyl substituted guaiacols found in cigarette smoke condensate.
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A series of alkyl and alkenyl substituted guaiacols, which comprise a group of biologically and organoleptically active compounds, have been synthesized. Mass spectra and GC retention times for these have been recorded and compared with those obtained for constituents of a weakly acidic fraction of smoke condensate derived from American blend type cigarettes. On the basis of these results, 25 guaiacols have been identified, 18 of which have not been detected in tobacco smoke condensate previously.
- Arnarp,Bielawski,Dahlin,Dahlman,Enzell,Pettersson
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