Beatrice Russo

Synthesis and biological evaluation of diastereoisomerically pure N,O-nucleosides.

Several N,O-nucleosides have been synthesized in good yields by direct 1,3-dipolar cyclization methodology, in the absence of solvent. A remarkable cis stereoselectivity (de 98%) was observed by tuning the substituents on the nitrone moiety. A good number of these N,O-nucleosides have been evaluated for cytotoxic activity against selected cellular lines. Some of the tested compounds have proven to be potential antiproliferative drugs.

Erbium(III) Chloride: a Very Active Acylation Catalyst

Erbium(iii) chloride is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides (Ac2O, (EtCO)2O, (PriCO)2O, (ButCO)2O, and (CF3CO)2), without isomerization of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity.

Efficient Organocatalyst Supported on a Simple Ionic Liquid as a Recoverable System for the Asymmetric Diels–Alder Reaction in the Presence of Water

The synthesis, characterization, and evaluation of a new highly efficient organocatalyst, namely, (5S)‐2,2,3‐trimethyl‐5‐thiobenzylmethyl‐4‐imidazolidinone hydrochloride, has been achieved. The catalyst possesses important structural features that should increase the catalytic efficiency and solubility in polar media. The application of the ionic‐liquid‐supported imidazolidinone catalyst in enantioselective Diels–Alder reactions was investigated. The Diels–Alder reactions of several dienes and dienophiles proceeded efficiently in the presence of the catalyst to provide the desired products in moderate to good yields and from good to excellent enantioselectivities. The conformation study confirms that in the transition state the Re face is shielded completely by the phenyl ring and an approach on the less hindered Si face is preferred. Particularly remarkable is the fact that the entire ionic liquid/HCl 0.01 M/catalyst system can be recovered and reused in up to six runs without an appreciable loss of catalytic activity.

Mild Oxidative Conversion of Nitroalkanes into Carbonyl Compounds in Ionic Liquids

Basic hydrogen peroxide and sodium perborate were found to be cheap and efficient alternatives for the conversion of primary and secondary nitro to carbonyl compounds (Nef reaction) in ionic liquids.

Modified N,O-Nucleosides: Design, Synthesis, and Anti-tumour Activity

A preliminary library of modified N,O-nucleosides was prepared and tested on a selected number of human cancer lines that include SKOV3, SW480, and K562. Thymine, N-benzyl substituents, and aromatic rings contribute to an increase of the biological activity, up to 10–25 μM, that appeared also reliant on the calculated lipophilicity of the nucleosides, expressed as cLogP, where P represents the partition coefficient of a solute between n-octanol and water.

Synthesis of 1,5-Functionalized 1,2,3-Triazoles Using Ionic Liquid/Iron(III) Chloride as Efficient and Reusable Homogeneous Catalyst

An efficient, eco-compatible and very cheap method for the construction of triazoles via eliminative azide–olefin cycloaddition (EAOC) reaction has been developed by a catalytic system IL/FeCl3, offering an highly regioselective approach to structurally diverse 1,5-disubstituted 1,2,3triazoles in up to 95% yield. This strategy features the reuse of catalytic system through simple operations. Mechanistic studies indicated that an asynchronous concerted dipolar cycloadditionelimination process might be involved.

Synthesis and gas sorption behaviour of ZIF-90 with large pore volume

Stoichiometric triethylamine in methanol produces sub-micron ZIF-90 in 98% yield with the largest gas uptakes ever measured. Micropore volume and surface area are compatible with an empty pore network and with crystallographic data, but the occurrence of crystal defects, such as missing ligands or Zn2+ ions, although improbable, can not be ruled out.