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Synthesis of α‐Imino Amidines and 2,3‐Diamino Indolenines Using a One‐Pot Graphene Oxide‐Catalyzed Process

Samantha Caputo, Silvia Donoso, Luca Banfi, Andrea Basso, więcej

European Journal of Organic Chemistry > 27 > 9 > n/a - n/a

The acid‐catalyzed three‐component (3 C) UGI reaction of isocyanides, amines, and aldehydes generally gives α‐amino amidines. Herein, we report the graphene oxide (GO)‐promoted promoted 3 C Ugi reaction followed by a C−N bond oxidation to provide rapid access to α‐imino amidines. GO plays a crucial role both in the multicomponent reaction and in the subsequent oxidation. Interestingly, α‐imino amidines...

artykuł

Strong genetic differentiation between fragmented alpine bush‐cricket populations demands preservation of evolutionary significant units

Isabel Martinez‐Sañudo, Andrea Basso, Giacomo Ortis, Federico Marangoni, więcej

Insect Conservation and Diversity > 15 > 6 > 752 - 762

The eastern alpine bush cricket, Anonconotus italoaustriacus Nadig, 1987, is a grassland species historically present in a few disjunct ranges in north‐eastern Italy and High Tauern in Austria. The species has recently been included in the Red List of the International Union for Conservation of Nature (IUCN) as an endangered species with a decreasing population trend. Information regarding the genetic...

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An outbreak of crayfish rickettsiosis caused by Coxiella cheraxi in redclaw crayfish (Cherax quadricarinatus) imported to Israel from Australia

Nadav Davidovich, Eleonora Fiocchi, Andrea Basso, Jane Budai, więcej

Transboundary and Emerging Diseases > 69 > 2 > 204 - 212

The redclaw crayfish (Cherax quadricarinatus) is a freshwater decapod crustacean, cultured in numerous countries worldwide for both food and ornamental purposes. Redclaw crayfish has become an important aquaculture species due to its physical and biological traits, relatively easy breeding, and a short growing‐out period to reach commercial size. Bacterial infections are the second‐most studied pathogens...

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Ketene 3‐Component Staudinger Reaction (K‐3CSR) to β‐Lactams: A New Entry in the Class of Photoinduced Multicomponent Reactions

Federica Minuto, Chiara Lambruschini, Andrea Basso

European Journal of Organic Chemistry > 2021 > 22 > 3270 - 3273

The Staudinger synthesis of β‐lactams from imines and ketenes has been conducted photochemically only in very limited cases. Recent advances in the visible light mediated Wolff rearrangement of diazoketones allowed us to perform, for the first time, a 3‐component Staudinger reaction, by mixing aldehydes, amines and diazoketones in the dark and switching the light on after imine formation. The new...

artykuł

A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives

Lisa Moni, Luca Banfi, Andrea Basso, Alessia Mori, więcej

European Journal of Organic Chemistry > 2021 > 11 > 1737 - 1749

A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93...

artykuł

Stereoselective Synthesis of 3,5‐Dihydroxypyrrolidin‐2‐ones Through a Photoinduced Multicomponent Reaction Followed by Dimerization

Enrico Bergamaschi, Pietro Capurro, Chiara Lambruschini, Renata Riva, więcej

European Journal of Organic Chemistry > 2019 > 34 > 5992 - 5997

A photoinduced reaction between diazoketones, isocyanides and silanols, followed by aldol dimerization of the resulting multicomponent adduct, affords polyfunctionalized 3,5‐dihydroxypyrrolidin‐2‐one heterocycles in a straightforward manner. Six new bonds and two quaternary carbons are formed in just two steps with this complexity‐generating methodology. A high degree of stereoselectivity is also...

artykuł

Anti-inflammatory Activity of Tocotrienols in Age-related Pathologies: A SASPected Involvement of Cellular Senescence

Marco Malavolta, Elisa Pierpaoli, Robertina Giacconi, Andrea Basso, więcej

Biological Procedures Online > 2018 > 20 > 1 > 1-10

Tocotrienols (T3) have been shown to represent a very important part of the vitamin E family since they have opened new opportunities to prevent or treat a multitude of age-related chronic diseases. The beneficial effects of T3 include the amelioration of lipid profile, the promotion of Nrf2 mediated cytoprotective activity and the suppression of inflammation. All these effects may be the consequence...

artykuł

Bicyclic Heterocycles from Levulinic Acid through a Fast and Operationally Simple Diversity‐Oriented Multicomponent Approach

Chiara Lambruschini, Andrea Basso, Lisa Moni, Alessandro Pinna, więcej

European Journal of Organic Chemistry > 2018 > 39 > 5445 - 5455

Levulinic acid, which is one of the most important renewable building blocks derived from lignocellulosic biomass, has been converted in a diversity‐oriented manner into two families of drug‐like bicyclic nitrogen heterocycles. The methodology, endowed with high step economy and operational simplicity, is based on an Ugi multicomponent reaction, which employs amino alcohols as components, followed...

artykuł

Measuring zinc in biological nanovesicles by multiple analytical approaches

Francesco Piacenza, Antje Biesemeier, Marco Farina, Francesco Piva, więcej

Journal of Trace Elements in Medicine and Biology > 2018 > 48 > C > 58-66

Exosomes are nanovesicles known to mediate intercellular communication. Although it is established that zinc ions can act as intracellular signaling factors, the measurement of zinc in circulating nanovesicles has not yet been attempted. Providing evidence of the existence of this zinc fraction and methods for its measurement might be important to advance our knowledge of zinc status and its relevance...

artykuł

Zr-mediated synthesis of chiral cyclic imines and their application in Betti reactions

Elena Speich, Luca Banfi, Lisa Moni, Renata Riva, więcej

Chemistry of Heterocyclic Compounds > 2018 > 54 > 3 > 329-333

A novel synthetic strategy has been outlined to assemble enantiomerically pure Betti bases with unprecedented structures. This involves the Zr-mediated reduction of pyrrolidin-2-ones to cyclic imines and their subsequent reaction with phenolic derivatives.

artykuł

Evidence of potential hybridization in the Thaumetopoea pityocampa‐wilkinsoni complex

Edoardo Petrucco‐Toffolo, Andrea Basso, Carole Kerdelhué, Kahraman İpekdal, więcej

Agricultural and Forest Entomology > 20 > 1 > 9 - 17

The winter pine processionary moth complex includes some major defoliating insects of Pinus and Cedrus forests in southern Europe and the Mediterranean Basin, where they also cause health problems to humans and animals. The complex includes at least two species that were separated recently based on molecular and morphological evidence: Thaumetopoea pityocampa in the west and Thaumetopoea wilkinsoni...

artykuł

Diversity‐Oriented Synthesis of Various Enantiopure Heterocycles by Coupling Organocatalysis with Multicomponent Reactions

Samantha Caputo, Luca Banfi, Andrea Basso, Andrea Galatini, więcej

European Journal of Organic Chemistry > 2017 > 45 > 6619 - 6628

Chiral, enantiopure 1,3‐amino alcohols, obtained through an organocatalytic Mannich reaction, have been used as starting materials for a concise sequence involving a diastereoselective Ugi reaction followed by various types of S_N2 cyclization. In this way, different enantiopure heterocycles have been prepared, with both scaffold and decoration diversity (up to four diversity inputs).

artykuł

Changes in Zn homeostasis during long term culture of primary endothelial cells and effects of Zn on endothelial cell senescence

Marco Malavolta, Laura Costarelli, Robertina Giacconi, Andrea Basso, więcej

Experimental Gerontology > 2017 > 99 > C > 35-45

Endothelial cell senescence and Zn nutritional status influence cardiovascular disease. The influence of Zn appears dichotomous, hence it is imperative to understand the relationship with cellular senescence to improve knowledge about the molecular and cellular basis of the disease. Here we aimed to determine: 1) the impact of chronic exposure to a moderately high dose of Zn on senescence of endothelial...

artykuł

A total evidence phylogeny for the processionary moths of the genus Thaumetopoea (Lepidoptera: Notodontidae: Thaumetopoeinae)

Andrea Basso, Enrico Negrisolo, Alberto Zilli, Andrea Battisti, więcej

Cladistics > 33 > 6 > 557 - 573

Processionary moths belong to a group of about 100 species well known for their social behaviour and their urticating systems. The genus Thaumetopoea s.l. includes about 15 species and has been divided into three genera (Helianthocampa, Thaumetopoea s.s., and Traumatocampa) in the last revision, based on key morphological features of the adults and on the host plants of the larvae. We performed a...

artykuł

Synthesis of seven-membered nitrogen heterocycles through the Ugi multicomponent reaction

Luca Banfi, Andrea Basso, Chiara Lambruschini, Lisa Moni, więcej

Chemistry of Heterocyclic Compounds > 2017 > 53 > 4 > 382-408

This paper reviews all the syntheses of 7-membered nitrogen heterocycles that are based on the Ugi multicomponent reaction. Different systems may be obtained in a diversity-oriented manner employing three general strategies: i) intramolecular Ugi reaction; ii) Ugi reaction followed by cyclization involving one additional functional group; iii) Ugi reaction followed by cyclization involving two additional...

artykuł

Different transcriptional profiling between senescent and non-senescent human coronary artery endothelial cells (HCAECs) by Omeprazole and Lansoprazole treatment

Laura Costarelli, Robertina Giacconi, Marco Malavolta, Andrea Basso, więcej

Biogerontology > 2017 > 18 > 2 > 217-236

Recent evidence suggests that high dose and/or long term use of proton pump inhibitors (PPIs) may increase the risk of adverse cardiovascular events in older patients, but mechanisms underlying these detrimental effects are not known. Taking into account that the senescent endothelial cells have been implicated in the genesis or promotion of age-related cardiovascular disease, we hypothesized an active...

artykuł

Photoinduzierte Mehrkomponentenreaktionen

Silvia Garbarino, Davide Ravelli, Stefano Protti, Andrea Basso

Angewandte Chemie > 128 > 50 > 15702 - 15711

Die Kombination von Mehrkomponentenansätzen mit lichtgetriebenen Prozessen erschließt neue Bereiche auf dem Gebiet der organischen Synthesechemie, deren Bedarf an nachhaltigen und atom‐ sowie energieeffizienten Reaktionen immer dringlicher wird. Photoinduzierte Mehrkomponentenreaktionen befinden sich noch immer in einem frühen Stadium, für die nahe Zukunft ist jedoch mit deutlichen Fortschritten zu...

artykuł

Photoinduced Multicomponent Reactions

Silvia Garbarino, Davide Ravelli, Stefano Protti, Andrea Basso

Angewandte Chemie International Edition > 55 > 50 > 15476 - 15484

The combination of multicomponent approaches with light‐driven processes opens up new scenarios in the area of synthetic organic chemistry, where the need for sustainable, atom‐ and energy‐efficient reactions is increasingly urgent. Photoinduced multicomponent reactions are still in their infancy, but significant developments in this area are expected in the near future.

artykuł

Access to Polycyclic Alkaloid‐Like Structures by Coupling the Passerini and Ugi Reactions with Two Sequential Metal‐Catalyzed Cyclizations

Martina Spallarossa, Luca Banfi, Andrea Basso, Lisa Moni, więcej

Advanced Synthesis & Catalysis > 358 > 18 > 2940 - 2948

Complex polycyclic compounds resembling some natural alkaloids have been prepared in only three high yielding steps by combining the Ugi or Passerini multicomponent reactions with two metal‐catalyzed cyclizations: an intramolecular Tsuji–Trost reaction of the isocyanide‐derived amide followed by a ring‐closing metathesis. Scaffold diversity may be explored by the appropriate choice of starting unsaturated...

artykuł

Differential anti-thrombotic benefit and bleeding risk profiles of antagonists of protease-activated receptor 1 and 4 in Cynomolgus Macaques

L. Alexandra Wickham, Gary Sitko, Maria Stranieri-Michener, Larry Handt, więcej

Thrombosis Research > 2016 > 145 > C > 133-139

Platelet activation plays a crucial role in hemostasis and thrombosis. Thrombin, the most potent stimulus of platelet activation, mediates platelet activation via the protease activated receptors (PARs). The platelet PAR repertoire in mediating thrombin's action differs across species. Only nonhuman primate (NHP) platelet activation is known to be similar to humans, mediated by PAR1 and PAR4, hence...

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