Search

A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenones and various mono-, bi- and tri-cyclic azoles can be tolerated and give terminal N-vinyl azoles in moderate to high yields. A plausible mechanism is also proposed. [ABSTRACT FROM AUTHOR]

Summary: The aim of this work was a chemical and biological characterisation of Fagiolina del Trasimeno (Italian cowpea landrace) in its coloured and white variants. After opening the package (T0), samples were addressed to a set of chemical and biological assays. Analyses were also conducted on cooked, 6‐month‐stored (T1) and commercial products. Chemical composition was comparatively analysed by nuclear magnetic resonance (NMR) of the proton. At both T0 and T1, raw coloured Fagiolina del Trasimeno showed statistically higher values in terms of phenolic content (T0: 11.51 mg GAE/g, T1: 9.34 mg GAE/g) and antioxidant activity (DPPH T0: 27.40 μmol TE/g, T1: 20.15 μmol TE/g; ABTS T0: 37.98 μmol CE/g, T1: 27.24 μmol CE/g) when compared with white/commercial variants. Globally, boiling, pressure‐cooking, and storage led to a loss in phenolic content and antioxidant activity. However, values in coloured samples generally remained higher than those observed in the other products. Finally, Fagiolina del Trasimeno extracts were shown to inhibit cyclooxygenase activity in HepG2 cells (up to −41.96%). In summary, these results highlighted interesting chemical and biological features of this product, showing the impact of routine procedures, as well. [ABSTRACT FROM AUTHOR]

An unprecedented Michael/intramolecular etherification cascade reaction of phenyl vinyl selenone with 3‐hydroxyoxindoles under aqueous basic conditions at room temperature is described. The method provides a domino access to new spirooxindole 2,2‐disubstituted oxetanes in moderate to good yields under mild reaction conditions. [ABSTRACT FROM AUTHOR]

Abstract Herein we disclose an efficient and flexible approach to biologically relevant 3,4-dihydropyrazino[1,2- a ]indol-1(2 H)ones and 3,4-dihydropyrrolo[1,2- a ]pyrazin-1(2 H)ones through a domino Michael/intramolecular nucleophilic substitution pathway using potassium hydroxide in dichloromethane. Variously substituted vinyl selenones and 1 H -indole-2-carboxamides or 1 H -pyrrole-2-carboxamides have been employed with success in chemo and regio-selective processes. The introduction of an amino acid portion on the amidic function is well tolerated without racemization. Graphical abstract Image 1 [ABSTRACT FROM AUTHOR]

A new organocatalytic protocol for the aerobic dehydrogenative allylation of alcohols using non-activated alkenes as the allylating reagent and ambient air as the terminal oxidant is established. Mechanistically, the procedure relies on the interplay of a diselane and a photoredox catalyst by means of a light-induced electron transfer process. Under optimized conditions, a broad range of both cyclic and acyclic ethers is accessed with very high functional group tolerance and excellent regioselectivity. [ABSTRACT FROM AUTHOR]

A simple and practical procedure for the oxidation of vinyl selenides into the corresponding selenones using Oxone in water at 60 °C has been reported. Structurally diverse phenyl vinyl selenones were oxidized under heterogeneous conditions without organic co‐solvents or additional catalysts. [ABSTRACT FROM AUTHOR]

Herein we report the synthesis of biologically relevant oxazino[4,3- a ]indoles by an environmentally friendly Michael addition-cyclization cascade using potassium hydroxide in dichloromethane employing variously substituted vinyl selenones and (1 H -indol-2yl)methanols. The addition of 18-crown-6, as a complexing agent, is crucial to achieve high chemo- and regio-selectivity. [ABSTRACT FROM AUTHOR]

Vinyl selenides, sulfides and tellurides surely represent important compounds in organic chemistry for their relatively easy accessibility and synthetic utility. More than the others vinyl selenides showed interesting biological activities such as the ability to reduce oxidative stress. New methods for the synthesis of vinyl thioethers have been developed in the last few years placing such compounds in a prominent position from an organic chemistry perspective. Tellurides are endowed with unique properties that make them suitable alternatives or precursors to organometallic species. The most recent and interesting examples about the chemistry of vinyl chalcogenides will be collected in this minireview. [ABSTRACT FROM PUBLISHER]

In recent years, vinyl selenones were rediscovered as useful building blocks for new synthetic transformations. This review will highlight these advances in the field of multiple-bond-forming reactions, one-pot synthesis of carbo- and heterocycles, enantioselective construction of densely functionalized molecules, and total synthesis of natural products. [ABSTRACT FROM AUTHOR]

Review: 53 refs. [ABSTRACT FROM AUTHOR]

Review: 55 refs. [ABSTRACT FROM AUTHOR]

In the last decades, organoselenium compounds gained interest due to their important biological features. However, the lack of solubility, which characterizes most of them, makes their actual clinical exploitability a hard to reach goal. Selenosugars, with their intrinsic polarity, do not suffer from this issue and as a result, they can be conceived as a useful alternative. The aim of this review is to provide basic knowledge of the synthetic aspects of selenosugars, selenonium salts, selenoglycosides, and selenonucleotides. Their biological properties will be briefly detailed. Of course, it will not be a comprehensive dissertation but an analysis of what the authors think is the cream of the crop of this interesting research topic. [ABSTRACT FROM AUTHOR]

A series of variously functionalized selenium-containing compounds were purposely synthesized and evaluated against a panel of cancer cell lines. Most of the compounds showed an interesting cytotoxicity profile with compound 5 showing a potent activity on MCF7 cells. The ethyl amino derivative 5 acts synergistically with cis-platin and inhibits the GST enzyme with a potency that well correlates with the cytotoxicity observed in MCF7 cells. A computational analysis suggests a possible binding mode on the GST enzyme. As the main outcome of the present study, the ethyl amino derivative 5 emerged as a valid lead compound for further, future developments. [ABSTRACT FROM AUTHOR]