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43 result(s) for "Van der Eycken, Erik"
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Inhibiting bacterial cooperation is an evolutionarily robust anti-biofilm strategy
Bacteria commonly form dense biofilms encased in extracellular polymeric substances (EPS). Biofilms are often extremely tolerant to antimicrobials but their reliance on shared EPS may also be a weakness as social evolution theory predicts that inhibiting shared traits can select against resistance. Here we show that EPS of Salmonella biofilms is a cooperative trait whose benefit is shared among cells, and that EPS inhibition reduces both cell attachment and antimicrobial tolerance. We then compare an EPS inhibitor to conventional antimicrobials in an evolutionary experiment. While resistance against conventional antimicrobials rapidly evolves, we see no evolution of resistance to EPS inhibition. We further show that a resistant strain is outcompeted by a susceptible strain under EPS inhibitor treatment, explaining why resistance does not evolve. Our work suggests that targeting cooperative traits is a viable solution to the problem of antimicrobial resistance. Bacterial biofilms rely on shared extracellular polymeric substances (EPS) and are often highly tolerant to antibiotics. Here, the authors show in in vitro experiments that Salmonella does not evolve resistance to EPS inhibition because such strains are outcompeted by a susceptible strain under inhibitor treatment.
Microwave-Assisted Post-Ugi Reactions for the Synthesis of Polycycles
Microwave irradiation and post-Ugi reactions own their respective advantages in comparison with other strategies. The combination of microwave irradiation and post-Ugi reactions shows paramount importance in the construction of polycycles. This minireview outlines the recent developments of microwave-assisted post-Ugi reactions for the synthesis of polycycles. Through transition metal-catalyzed or transition metal-free transformations, diverse polycycles are prepared in an efficient, rapid, and step-economical manner.
Recent Advances in the Synthesis of Rosettacin
Camptothecin and its analogues show important antitumor activity and have been used in clinical studies. However, hydrolysis of lactone in the E ring seriously attenuates the antitumor activity. To change this situation, aromathecin alkaloids are investigated in order to replace camptothecins. Potential antitumor activity has obtained more and more attention from organic and pharmaceutical chemists. As a member of the aromathecin alkaloids, rosettacin has been synthesized via different methods. This review summarizes recent advances in the synthesis of rosettacin.
Synthetic Strategies in the Preparation of Phenanthridinones
Phenanthridinones are important heterocyclic frameworks present in a variety of complex natural products, pharmaceuticals and displaying wide range of pharmacological actions. Its structural importance has evoked a great deal of interest in the domains of organic synthesis and medicinal chemistry to develop new synthetic methodologies, as well as novel compounds of pharmaceutical interest. This review focuses on the synthesis of phenanthridinone scaffolds by employing aryl-aryl, N-aryl, and biaryl coupling reactions, decarboxylative amidations, and photocatalyzed reactions.
Recent Developments in Transition-Metal Catalyzed Direct C–H Alkenylation, Alkylation, and Alkynylation of Azoles
The transition metal-catalyzed C–H bond functionalization of azoles has emerged as one of the most important strategies to decorate these biologically important scaffolds. Despite significant progress in the C–H functionalization of various heteroarenes, the regioselective alkylation and alkenylation of azoles are still arduous transformations in many cases. This review covers recent advances in the direct C–H alkenylation, alkylation and alkynylation of azoles utilizing transition metal-catalysis. Moreover, the limitations of different strategies, chemoselectivity and regioselectivity issues will be discussed in this review.
Recent Advances in Phthalan and Coumaran Chemistry
Oxygen‐containing heterocycles are common in biologically active compounds. In particular, phthalan and coumaran cores are found in pharmaceuticals, organic electronics, and other useful medical and technological applications. Recent research has expanded the methods available for their synthesis. This Minireview presents recent advances in the chemistry of phthalans and coumarans, with the goal of overcoming synthetic challenges and facilitating the applications of phthalans and coumarans. O me, O my! Oxygen‐containing heterocycles are common in biologically active compounds. In particular, phthalan and coumaran cores are found in pharmaceuticals, organic electronics, and other useful medical and technological applications. This Minireview presents recent advances in the chemistry of phthalans and coumarans, with the goal of overcoming synthetic challenges and facilitating their application.
Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp 2 )–H activation and C(sp 3 )–H amination
A rhodium(III)-catalyzed intramolecular oxidative annulation of O -substituted N -hydroxyacrylamides for the construction of indolizinones via sequential C(sp 2 )–H activation and C(sp 3 )–H amination has been developed. This approach shows excellent functional-group tolerance. The synthesized scaffold forms the core of many natural products with pharmacological relevance.
Microwave-Assisted Synthesis of Fluorescent Pyrido2,3-bindolizines from Alkylpyridinium Salts and Enaminones
Pyridinium ylides are well recognized as dipoles for cycloaddition reactions. In its turn, the microwave-assisted interaction of N-(cyanomethyl)-2-alkylpyridinium salts with enaminones unexpectedly proceeds as a domino sequence of cycloisomerization and cyclocondensation reactions, instead of a 1,3-dipolar cycloaddition. The reaction takes place in the presence of sodium acetate as base and employs benign solvents. The optical properties of the resulting pyrido[2,3-b]indolizines were studied, showing green light emission with high fluorescence quantum yields.
Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
An efficient sequence based on the Ugi-azide reaction and rhodium(III)-catalyzed intermolecular annulation has been established for the preparation of tetrazole-isoquinolone/pyridone hybrids. Several N -acylaminomethyltetrazoles were reacted with arylacetylenes to form the hybrid products in moderate to very good yields. The method relies on the capacity of the rhodium catalyst to promote C(sp 2 )–H activation in the presence of a suitable directing group. The Ugi-azide reaction provides broad molecular diversity and enables the introduction of the tetrazole moiety, which may further assist the catalytic reaction by coordinating the metal center. The scope of the isoquinolones is very wide and may be extended to the preparation of complex compounds having heterocyclic moieties such as pyridone, furan, thiophene and pyrrole, as well as the corresponding benzo-fused derivatives. The developed procedure is simple, reproducible and does not require inert conditions.
Enhanced Mechanical Robustness of Sprayed Cellulose Nanofibril Coatings Through Internal Crosslinking with Boric Acid
The enhanced mechanical durability of sprayed nanocellulose coatings at the macroscopic level is primarily required to promote their application in demanding industrial applications with frequently exposed surfaces. In this study, different coating configurations are designed by spraying aqueous cellulose nanofiber (CNF) suspensions in combination with boric acid (BA) as an internal crosslinker and polydopamine (PDA) as an adhesive interlayer onto glass substrates. Multilayer coatings (CNF/BA) or mixed-layer coatings (CNF + BA) with various concentrations of BA and numbers of sprayed layers are evaluated for maximized mechanical performance based on tape tests, rub tests, cross-cut tests, and scratching tests. Good adhesive strength was realized with an interlayer of PDA/BA (high-concentration BA = 10 mM). The highest cohesive strength was observed for a mixed CNF + BA coating (high-concentration BA = 10 mM) with a scratch resistance of 9 N, and a multilayer CNF/BA coating (gradient layers with ultra-high BA concentration = 100 mM) with a scratch resistance of 8 N. The coatings with the highest density did not uniquely introduce the best mechanical resistance when comparing CNF/BA and CNF + BA coatings, as the formation of BA crystals in multilayer coatings might negatively affect the mechanical properties through embrittlement. Alternatively, the mixed CNF + BA coatings with high BA concentrations provide high density and the best mechanical resistance. The favorable crosslinking corresponds to stabilized water contact angles and reduced spreading of the water as a function of time, while a decrease in coating density causes a reduction in transparency. The chemical interactions between CNF and BA are illustrated by infrared spectroscopy, confirming a reduction in free hydroxyl groups upon crosslinking.