2/4-Substituted-9-fluorenones and their O-glucosides as potential immunomodulators and anti-herpes simplex virus-2 agents. Part 5

Arena, Adriana; Arena, Nicoletta; Gregorio, Ambra De; Maccari, Rosanna; Ottanà, Rosaria; Pavone, Bernadette; Tramice, Annabella; Trincone, Antonio; Vigorita, Maria Gabriella

doi:10.1016/j.ejmech.2008.01.045

Cited by 13 publications

(7 citation statements)

References 34 publications

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“…Threrefore, and taking into account the technological and biomedical importance of fluoren-9-ones, their usefulness as synthetic intermediates and their occurrence as natural products, [15] we also decided to devise a new strategy toward 8.…”

Section: Resultsmentioning

confidence: 99%

Electrocyclization‐Mediated Approach to 2‐Methyltriclisine, an Unnatural Analog of the Azafluoranthene Alkaloid Triclisine

Silveira¹,

Larghi²,

Mendes³

et al. 2009

Eur J Org Chem

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The synthesis of 2‐methyltriclisine, an unnatural analog of the azafluoranthene alkaloid triclisine, is reported. The synthesis was achieved in 10 steps and 21 % overall yield from 2‐bromo‐3,4‐dimethoxybenzaldehyde, through the intermediacy of 3,4‐dimethoxyfluoren‐9‐one. Construction of the heterocyclic ring entailed the para‐Claisen rearrangement of an allyl‐4‐fluorenyl ether, followed by isomerization of the resulting 2‐allylfluoren‐9‐one and a microwave‐assisted electrocyclization of the aza 6π‐electron system formed by oximation of its carbonyl function. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

Electrocyclization‐Mediated Approach to 2‐Methyltriclisine, an Unnatural Analog of the Azafluoranthene Alkaloid Triclisine

Silveira¹,

Larghi²,

Mendes³

et al. 2009

Eur J Org Chem

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“…Finally, the feasibility of efficient naringin glucosylation directly within grapefruit juice is also demonstrated at low maltose concentrations and optimal pH of the enzyme [63]. Other acceptors belonging to 9-fluorenone derivatives (Figure 3) were used providing several α- O -polyglucosides which were useful for a quick screening of the pharmaceutical profile as modified by carbohydrate(s) moieties with respect to parental antiviral aglycones [64]. …”

Section: Habitat-related Properties Of Marine Biocatalystsmentioning

confidence: 99%

Marine Biocatalysts: Enzymatic Features and Applications

2011

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In several recent reports related to biocatalysis the enormous pool of biodiversity found in marine ecosystems is considered a profitable natural reservoir for acquiring an inventory of useful biocatalysts. These enzymes are characterized by well-known habitat-related features such as salt tolerance, hyperthermostability, barophilicity and cold adaptivity. In addition, their novel chemical and stereochemical characteristics increase the interest of biocatalysis practitioners both in academia and research industry. In this review, starting from the analysis of these featuring habitat-related properties, important examples of marine enzymes in biocatalysis will be reported. Completion of this report is devoted to the analysis of novel chemical and stereochemical biodiversity offered by marine biocatalysts with particular emphasis on current or potential applications of these enzymes in chemical and pharmaceutical fields. The analysis of literature cited here and the many published patent applications concerning the use of marine enzymes supports the view that these biocatalysts are just waiting to be discovered, reflecting the importance of the marine environment. The potential of this habitat should be thoroughly explored and possibly the way to access useful biocatalysts should avoid destructive large-scale collections of marine biomass for enzyme production. These two aspects are day by day increasing in interest and a future increase in the use of marine enzymes in biocatalysis should be expected.

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“…As in the previously studied series of compounds [18,20,21,25] all derivatives 1-12 were used for a pharmacological screening to evaluate cytotoxicity, IFN-a, TNF-a, and IL-12 inducing properties, and antiviral activity against HSV-2 on human PBMC. Table 1 shows the effects of different concentrations of compounds on cell viability.…”

Section: Biological Studiesmentioning

confidence: 99%

“…[31,32] This biocatalyst was also very recently used by us to synthesize structurally related O-a-oligoglucosides of different 9-fluorenones possessing spacers in different positions, as potential immunomodulators and anti-HSV-2 agents. [20] Commercial almond b-glucosidase and Aspergillus oryzae b-galactosidase are known enzymes usually adopted for the synthesis of bgluco-and b-galactosides of a different nature, [26a, c] however, to the best of our knowledge they were never applied to tricyclic aromatic scaffolds such as 9-fluorenylmethanol.…”

Section: Introductionmentioning

confidence: 99%

“…This trend was also previously observed. [20] Interestingly in both the b-xyloside and a-glucoside series, polyglycosylation caused activity to increase in direct correlation with molecular weight: tetraxyloside 4 and tetraglucoside 10 prove to be the best derivatives, worthy of being analyzed for DNA binding properties. [19] In addition, subtle structural differences as in monogly-…”

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confidence: 98%

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Facile Biocatalytic Access to 9‐Fluorenylmethyl Polyglycosides: Evaluation of Antiviral Activity on Immunocompetent Cells

Tramice¹,

Arena²,

Gregorio³

et al. 2008

ChemMedChem

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The biological activities of a series of mono- and oligosaccharides (beta-xylosides and alpha-glucosides) of 9-fluorenylmethanol were investigated together with mono-beta-galactoside and beta-glucoside of this aglycone, produced by biocatalytic routes. By using marine glycoside hydrolases and inexpensive donors such as maltose or xylan, access to mono-alpha-glucoside or mono-beta-xyloside of 9-fluorenylmethanol was obtained. Additionally, interesting polyglycoside derivatives were isolated. Biological testing indicated that in vitro treatment with these carbohydrate derivatives may influence the balance of cytokines in the environment of human peripheral blood mononuclear cells (PBMC), restricting the harmful effect of herpes simplex type 2 replication. In fact, these carbohydrate derivatives tested in WISH cells did not show any significant antiviral activity.

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2/4-Substituted-9-fluorenones and their O-glucosides as potential immunomodulators and anti-herpes simplex virus-2 agents. Part 5

Cited by 13 publications

References 34 publications

Electrocyclization‐Mediated Approach to 2‐Methyltriclisine, an Unnatural Analog of the Azafluoranthene Alkaloid Triclisine

Electrocyclization‐Mediated Approach to 2‐Methyltriclisine, an Unnatural Analog of the Azafluoranthene Alkaloid Triclisine

Marine Biocatalysts: Enzymatic Features and Applications

Facile Biocatalytic Access to 9‐Fluorenylmethyl Polyglycosides: Evaluation of Antiviral Activity on Immunocompetent Cells

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