Synthesis and antifungal activities of natural and synthetic biflavonoids

Sagrera, Gabriel; Bertucci, Anthony; Vázquez, Álvaro; Seoane, Gustavo

doi:10.1016/j.bmc.2011.04.010

Cited by 59 publications

(29 citation statements)

References 64 publications

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“…Biflavonoids are flavonoid dimers that have been attached to each other by either C-C or C-O-C bonds representing a variety of chemical structures [2]. Several biological activities such as antioxidant [3,4], antiviral [5], hypolipidemic [6], antidiabetic [7], anti-tumoral [8], antituberculosis [9], antimalarial [10], antibacterial [11], antifungal [12], and anti-inflammatory [13] effects have been reported for biflavonoids.…”

Section: Introductionmentioning

confidence: 99%

Molecular docking and quantum mechanical studies on biflavonoid structures as BACE-1 inhibitors

et al. 2014

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Beta-site amyloid precursor protein cleaving enzyme (BACE-1) is a well-known therapeutic target for Alzheimer disease (AD) due to its characteristic role in the pathogenesis of AD. Numerous researches have been focused on the design and development of potent peptidic and nonpeptidic BACE-1 inhibitors. In the present contribution, a series of experimentally validated biflavonoid BACE-1 inhibitors (1-21) were subjected to our structure-based molecular modeling studies. Binding modes were elucidated through molecular docking in the active site of the enzyme. Relatively good correlations between the theoretical and experimental binding affinities could be achieved (R 2 = 0.61). Analysis of intermolecular binding energy components was performed via functional B3LYP in association with splitvalence basis set using polarization functions (Def2-SVP), and structure-binding relationships were further elucidated through ligand-residue binding energies. Since little studies have been performed on the modeling and structure activity/binding relationships of biflavonoid structures as BACE-1 inhibitors, the results of this study may be useful in further extending the scope of biflavonoid structures as potential anti-Alzheimer scaffolds.

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Section: Introductionmentioning

confidence: 99%

Molecular docking and quantum mechanical studies on biflavonoid structures as BACE-1 inhibitors

et al. 2014

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“…KOH gave 57 % yield of the desired product 11 a . Further screening of other bases afforded a very good yield (82 %) of 11 a , and NaH was proved to be optimal for this transformation . Furthermore, a series of substituted aldehydes (1 equiv) were allowed to undergo Claisen–Schmidt condensation with 8 (1 equiv) in the presence of NaH (2 equiv) in anhydrous THF at room temperature (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…KOH gave 57 %y ield of the desired product 11 a.F urther screening of other bases afforded av ery good yield (82 %) of 11 a,a nd NaH was proved to be optimal for this transformation. [26] Furthermore, as eries of substituted aldehydes (1 equiv) were allowed to undergo Claisen-Schmidt condensation with 8 (1 equiv) in the presence of NaH (2 equiv) in anhydrous THF at room temperature ( Table 2). The products 11 were readily obtained by recrystallization from ethanol after acidifying the solutiont op H1.R eactions involving electron-withdrawing and electron-donating substituents on benzene rings all proceeded well to afford good to very good yields of 11 (Table 2).…”

Section: Synthesis Of Angular 3-methylfuranochalcones(11)mentioning

confidence: 99%

Diversity-Oriented Synthesis of Natural-Product-like Libraries Containing a 3-Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors

Chen

Lin

et al. 2016

ChemistryOpen

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Natural products are a major source of biological molecules. The 3‐methylfuran scaffold is found in a variety of plant secondary metabolite chemical elicitors that confer host‐plant resistance against insect pests. Herein, the diversity‐oriented synthesis of a natural‐product‐like library is reported, in which the 3‐methylfuran core is fused in an angular attachment to six common natural product scaffolds—coumarin, chalcone, flavone, flavonol, isoflavone and isoquinolinone. The structural diversity of this library is assessed computationally using cheminformatic analysis. Phenotypic high‐throughput screening of β‐glucuronidase activity uncovers several hits. Further in vivo screening confirms that these hits can induce resistance in rice to nymphs of the brown planthopper Nilaparvata lugens. This work validates the combination of diversity‐oriented synthesis and high‐throughput screening of β‐glucuronidase activity as a strategy for discovering new chemical elicitors.

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“…), 314(15); HRMS (EI) Calcd for C 23 H 24 ClNO6 : 445.12926 : 445. . Found: 445.1276.Methyl 3-Acetyl-4-(cyclohexylamino)-1-hydroxy-9-oxo-2,9-dihydro-1H-xanthene-1-carboxylate (6i).…”

mentioning

confidence: 99%

Regioselective Tandem [4 + 1]–[4 + 2] Synthesis of Amino-Substituted Dihydroxanthones and Xanthones

2015

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A highly convergent and operationally simple approach to mycotoxin-related 4-amino-substituted 1-hydroxydihydroxanthones is described. The target compounds are obtained in one pot by the multicomponent reaction of 3-carbonylchromones, isocyanides, and nonsymmetric dienophiles. The reaction, which involves a tandem [4 + 1]-[4 + 2] cycloaddition, efficiently affords a variety of both monomeric and dimeric polysubstituted dihydroxanthones structurally similar to bioactive ergochromes. Further aromatization to the corresponding xanthones is readily achieved by treatment with DBU under microwave irradiation.

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Synthesis and antifungal activities of natural and synthetic biflavonoids

Cited by 59 publications

References 64 publications

Molecular docking and quantum mechanical studies on biflavonoid structures as BACE-1 inhibitors

Molecular docking and quantum mechanical studies on biflavonoid structures as BACE-1 inhibitors

Diversity-Oriented Synthesis of Natural-Product-like Libraries Containing a 3-Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors

Regioselective Tandem [4 + 1]–[4 + 2] Synthesis of Amino-Substituted Dihydroxanthones and Xanthones

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