- Phenyliodine(III) Bis(trifluoroacetate) Mediated Synthesis of 6-Piperidinylpurine Homo-N-nucleosides Modified with Isoxazolines or Isoxazoles
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The room temperature, 1,3-dipolar cycloaddition reactions of the nitrile oxide obtained from (6-piperidin-1-yl-9H-purin-9-yl)acetaldehyde oxime upon phenyliodine(III) bis(trifluoroacetate) treatment with excess unsaturated alcohols as solvent resulted in isoxazoline or isoxazole derivatives in almost quantitative yields. Analogous derivatives were prepared from the reactions of unsaturated phosphates. Preliminary biological tests indicated inhibition of lipid peroxidation for some of the examined compounds.
- Balalas, Thomas,Peperidou, Catherine,Hadjipavlou-Litina, Dimitra J.,Litinas, Konstantinos E.
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- Design, synthesis and in vitro biological evaluation of a novel class of anti-adenovirus agents based on 3-amino-1,2-propanediol
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Nowadays there is not an effective drug for the treatment of infections caused by human adenovirus (HAdV) which supposes a clinical challenge, especially for paediatric and immunosuppressed patients. Here, we describe the design, synthesis and biological evaluation as anti-adenovirus agents of a new library (57 compounds) of diester, monoester and triazole derivatives based on 3-amino-1,2-propanediol skeleton. Seven compounds (17, 20, 26, 34, 44, 60 and 66) were selected based on their high anti-HAdV activity at low micromolar concentration (IC50 from 2.47 to 5.75 μM) and low cytotoxicity (CC50 from 28.70 to >200 μM). In addition, our mechanistic assays revealed that compounds 20 and 44 might be targeting specifically the HAdV DNA replication process, and compound 66 would be targeting HAdV E1A mRNA transcription. For compounds 17, 20, 34 and 60, the mechanism of action seems to be associated with later steps after HAdV DNA replication.
- Mazzotta, Sarah,Berastegui-Cabrera, Judith,Vega-Holm, Margarita,García-Lozano, María del Rosario,Carretero-Ledesma, Marta,Aiello, Francesca,Vega-Pérez, José Manuel,Pachón, Jerónimo,Iglesias-Guerra, Fernando,Sánchez-Céspedes, Javier
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- Synthesis of (1,2,3‐triazol‐4‐yl)methyl phosphinates and (1,2,3‐Triazol‐4‐yl)methyl phosphates by copper‐catalyzed azide‐alkyne cycloaddition
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An efficient and practical method was developed for the synthesis of new (1,2,3‐triazol‐4‐yl)methyl phosphinates and (1,2,3‐triazol‐4‐yl)methyl phosphates by the copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) of organic azides and prop‐2‐ynyl phos
- Tripolszky, Anna,Németh, Krisztina,Szabó, Pál Tamás,Bálint, Erika
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- Cross-hetero-dehydrogenative coupling reaction of phosphites: A catalytic metal-free phosphorylation of amines and alcohols
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Phosphorylation of amines, alcohols, and sulfoximines are accomplished using molecular iodine as a catalyst and H2O2 as the sole oxidant under mild reaction conditions. This method provides an easy route for synthesizing a variety of phosphoramidates, phosphorus triesters and sulfoximine-derived phosphoramidates which are of biological importance.
- Dhineshkumar, Jayaraman,Prabhu, Kandikere Ramaiah
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supporting information
p. 6062 - 6065
(2014/01/06)
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- Highly regioselective coupling reactions of allylic and propargylic alcohol derivatives with γ,γ-dialkoxyallylic zirconium species via Zr-to-Cu transmetalation
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(Chemical Equation Presented) In the presence of CuCN, reaction of γ,γ-dialkoxyallylic zirconium species 4, generated in situ by treating triethyl orthoacrylate with zirconocene-butene complex, with allylic and propargylic phosphates proceeded at the α-po
- Sato, Azusa,Ito, Hisanaka,Taguchi, Takeo
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p. 709 - 712
(2007/10/03)
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- Phosphorylation of alcohols with N-phosphoryl oxazolidinones employing copper(II) triflate catalysis
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(Chemical Equation Presented) Phosphoryl transfer from N-phosphoryl 5,5-diphenyl oxazolidinone is efficiently catalyzed by copper(II) triflate. The utility of this method has been demonstrated in the phosphorylation of representative primary, secondary, tertiary, phenolic, and allylic alcohols. These reaction conditions are significantly milder than employing alkoxides and allow the phosphorylation of biologically relevant molecules.
- Jones, Simon,Smanmoo, Chaiwat
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p. 3271 - 3274
(2007/10/03)
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- N-Phosphoryl oxazolidinones as effective phosphorylating agents
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A number of N-phosphoryl oxazolidinones have been prepared and evaluated, the best being 5,5-diphenyl oxazolidinones, the utility of which was demonstrated in the phosphorylation of a number of representative primary, secondary, tertiary, and phenolic alcohols.
- Jones, Simon,Smanmoo, Chaiwat
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p. 1585 - 1588
(2007/10/03)
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- A simple, general and improved procedure for phosphorylation of alcohols catalyzed by indium(III) chloride
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A general and efficient procedure has been developed for the preparation of dialkyl phosphate esters by indium(III) chloride catalyzed phosphoryl transfer from diethyl and diphenyl chlorophosphate to a variety of alcohols and phenols in THF in presence of triethylamine.
- Ranu, Brindaban C.,Das, Arijit
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p. 1063 - 1064
(2007/10/03)
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- Allyl- and propargylchromium reagents generated by a chromium(III) ate-type reagent as a reductant and their reactions with electrophiles
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A chromium ate-type reagent 'Bu5CrLi2' reacts with allylic and propargylic phosphates to generate the corresponding allyl- and propargylchromium (propargyl = prop-2-ynyl) reagents which further react with a variety of electrophiles such as aldehydes, ketones, imines, and isocyanates to afford the corresponding adducts in high yields.
- Hojo,Sakuragi,Okabe,Hosomi
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p. 357 - 358
(2007/10/03)
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- Preparation of phosphoric acid propargyl esters
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A process for the preparation of a phosphoric acid propargyl ester of the formula STR1 wherein R1 and R2 each independently is an aryl radical or a C1-4 -alkyl, C1-4 -alkenyl or C1-4 -alkynyl radical, and X, Y and Z each independently is oxygen or sulphur, comprising reacting a phosphoric acid monoester chloride or diester chloride with at least the equivalent amount of propargyl alcohol in a two-phase system in the presence of an inorganic base as an acid-trapping agent, and a catalyst comprising about 0.001 to 100 mol %, relative to the phosphoric acid ester chloride, of a tertiary amine or quaternary ammonium or phosphonium salt with at least 9 C atoms. Advantageously the catalyst is present in about 0.01 to 10 mol % relative to the phosphoric acid ester chloride and is a tertiary amine or quaternary ammonium salt, X, Y and Z are oxygen, R1 is propargyl and R2 is C1-4 -alkyl, the reaction is effected in the presence of methylene chloride, chloroform or toluene as solvent, the base is used in at least the equivalent amount and is selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates and alkaline earth metal carbonates.
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