Monitoraggio dell'accumulo di idrocarburi policiclici aromatici (IPA) in specie spontanee

ItLa flora del Salento rappresenta una grande risorsa per le applicazioni biotecnologiche. Presso l’Orto Botanico del DiSTeBA sono state propagate e moltiplicate tre specie spontanee molto comuni come il cardo mariano Silybum marianum (L.) Gaertner, il grespino Sonchus oleraceus L.e la cicoria selvatica Cichorium intybus L., al fine di verificare tecniche colturali che garantiscano un’adeguata produzione da destinare al settore alimentare, all’industria farmaceutica ed agli interventi di recupero ambientale. Nel presente lavoro si riportano i risultati relativi alla propagazione delle tre specie ed al monitoraggio dell’assorbimento che tali specie hanno evidenziato nei confronti degli Idrocarburi Policiclici Aromatici. Gli esiti delle attività hanno confermato una loro possibile applicazione nelle tecnologie riguardanti la fitodepurazione.EnThe Salentine flora represents a very rich source for biotechnological application. At the Botanic Garden of DiSTeBA, were propagated three wild species very common: Silybum marianum (L.) Gaertner, Sonchus oleraceus L. and Cichorium intybus L. We tried to evaluate the possibility of a “domestication” of these wild plants, to obtain an adequate production for the food industry, pharmaceutical industry and the environmental restoration measures. In this paper we report the results for the propagation of the three species and monitoring the absorption capacity that these species have shown towards Polycyclic Aromatic Hydrocarbons. The results confirmed their possible application in technologies and to perform an action of phytoremediation in respect of such pollutants ubiquitous and highly damaging

A Glycerol-Based Deep Eutectic Solvent as Natural Medium and Organic Reductant for Homocoupling of (Hetero)Aryl Chlorides: a Green Route to 2,2’-Bipyridine and Biaryl Scaffolds

A glycerol-based Deep Eutectic Solvent (DES) enables the Pd-catalyzed activation of (hetero)arylchlorides and promotes the formation of 2,2’-bipiyridines and biaryls through an Ullmann-type homocoupling in smooth experimental conditions (80 °C) with Ca(OH)2 as a green base and Pd/C as heterogeneous catalyst. Noteworthy, the coupling does not need the addition of external reducing agents, like metals, since the glycerol present in the DES acts as a safe and green organic reductant. The heterogeneous catalytic system (DES-Pd/C) showed to be easily recyclable and has been applied to the sustainable synthesis of the Abametapir drug

Design, stereoselective synthesis, configurational stability and biological activity of 7-chloro-9-(furan-3-yl)-2,3,3a,4-tetrahydro-1H-benzo[e]pyrrolo[2,1-c][1,2,4]thiadiazine 5,5-dioxide

Chiral 5-arylbenzothiadiazine derivatives have recently attracted particular attention because they exhibit an interesting pharmacological activity as AMPA receptor (AMPAr) positive modulators. However, investigations on their configurational stability suggest a rapid enantiomerization in physiological conditions. In order to enhance configurational stability, preserving AMPAr activity, we have designed the novel compound (R,S)-7-chloro-9-(furan-3-yl)-2,3,3a,4-tetrahydro-1H-benzo[e]pyrrolo[2,1-c][1,2,4]thiadiazine 5,5-dioxide bearing a pyrrolo moiety coupled with the 5-(furan-3-yl) substituent on benzothiadiazine core. A stereoselective synthesis was projected to obtain single enantiomer of the latter compound. Absolute configuration was assigned by X-ray crystal structure. Patch clamp experiments evaluating the activity of single enantiomers as AMPAr positive allosteric modulator showed that R stereoisomer is the active component. Molecular modeling studies were performed to explain biological results. An on-column stopped-flow bidimensional recycling HPLC procedure was applied to obtain on a large scale the active enantiomer with enantiomeric enrichment starting from the racemic mixture of the compound

Heterocycle Synthesis through Pd-Catalyzed Carbonylative Coupling

Heterocyclic chemistry is one of the most important and attractive areas of organic chemistry. It involves the preparation of compounds endowed with very high structural diversity and plays a central role in a multitude of highly developed areas: fine chemicals, drugs, flavors, dyes, engineered materials, and many other kinds of products contain at least one heterocyclic ring in their molecular structure. Therefore, the discovery of new methods for heterocycle synthesis is a significant objective of modern organic chemists, especially if prepared in environmentally benign and synthetically efficient ways. In this context, this minireview focuses on the synergy of two green strategies, namely multicomponent reactions and palladium-catalyzed carbonylations, for the construction of a wide variety of heterocyclic systems. These processes are of considerable interest because they combine synthetic efficiency with respect for the environment

Synthesis and isomerization of N-alpha-aza-heteroaryl-beta-lactams

The [2+2] carbonylative cycloaddition of N-cx-aza-heteroaryl substituted imines with allyl bromide led partially to beta-lactams, which underwent isomerization to the more stable alpha,beta-unsaturated carbonyl compound. Pyrimidinone derivatives together with doubly unsaturated amides represent the remaining isolated products. The strong electron-withdrawing effect of the two alpha-aza-heterocycles linked to the nitrogen atom and to the C4 of the 2-azetidinone structure could give a ring expansion, through a 2-azetinone intermediate that affords the pyrimidinone compounds. The substituted amides, instead, should result from a ring-opening reaction of the beta-lactam. (c) 2006 Elsevier Ltd. All rights reserved

Stereoselective synthesis of 3,4-diaryl-beta-lactams

Novel 3,4-diaryl beta-lactams were prepared with high stereoselectivity in an efficient manner by a palladium- catalyzed [2+2] carbonylative cycloaddition of benzyl halides with heteroarylidene amines. The type of alkyl group linked to the nitrogen atom influences the reaction’s stereoselectivity. Moreover, using chiral imines, separable diastereomeric mixtures of chiral 3,4-diaryl-beta-lactams were isolated with good yields and high trans diastereoselections

One-pot amide synthesis from allyl or benzyl halides and amines by Pd-catalysed carbonylation

Amides can be prepared from allyl or benzyl halides and primary or secondary amines, using Pd(0) catalyst under CO pressure, in a one-pot synthesis. The reaction proceeds through the acyl palladium halide formation which undergoes an acylic nucleophilic substitution from the amine