1486-51-7Relevant articles and documents
Preparation and mesomorphic properties of highly fluorinated materials incorporating S-ethyl-lactate
De Givenchy, Elisabeth Taffin,Guittard, Frederic,Geribaldi, Serge
, p. 91 - 98 (2001)
The synthesis of three different chiral short molecular weight compounds have been reported. The overall compounds incorporate a linear perfluorinated tail and S-ethyl-Iactate as chiral moiety. Each compound differ to the other by one molecular parameter: a spacer carbonyloxy or oxycarbonylmethoxy or by the presence or not of an ester function between the two aromatic rings of the mesogenic core. The synthesis have been carried out from 2-F-hexylethyliodide or 2-F-hexylethanol. The mesomorphic properties have been characterized by light microscopy and by differential thermal analysis showing the peculiar effect of the spacer. The two biphenyl derivatives exhibit liquid crystal properties over a wide temperature range. The mesophase for both compounds is smectic of type A. However, the introduction of an ester function in the core contribute to enhance the melting temperature and suppress the liquid crystal behavior.
Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture
Kühl, Nikos,Leuthold, Mila M.,Behnam, Mira A. M.,Klein, Christian D.
, p. 4567 - 4587 (2021/05/06)
The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.
Micellar Catalysis for Sustainable Hydroformylation
Calamante, Massimo,Dei, Filippo,Maramai, Samuele,Migliorini, Francesca,Petricci, Elena
, p. 2794 - 2806 (2021/05/03)
It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini's salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.
