111479-08-4Relevant articles and documents
Supramolecularly regulated copper-bisoxazoline catalysts for the efficient insertion of carbenoid species into hydroxyl bonds
Iniesta, Ester,Vidal-Ferran, Anton
, p. 6364 - 6367 (2020/06/21)
The catalytic insertion of copper carbenoids into O-H bonds affords synthetically useful α-alkyl/aryl-α-alkoxy/aryloxy derivatives. Herein, the design, preparation and application of supramolecularly regulated copper(i) complexes of bisoxazoline ligands is reported. We have demonstrated that the catalytic performance of these systems can be modulated by the use of an external molecule (i.e.the regulation agent), which interacts with a polyethyleneoxy chain on the ligand (i.e.the regulation site)viasupramolecular interactions. This approach has been applied to an array of structurally diverse alcohols (cycloalkyl, alkyl and aryl derivatives). Moreover, we have used this methodology to synthesise advanced synthetic intermediates of biologically relevant compounds.
Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
Carocci, Alessia,Catalano, Alessia,Lovece, Angelo,Lentini, Giovanni,Duranti, Andrea,Lucini, Valeria,Pannacci, Marilou,Scaglione, Francesco,Franchini, Carlo
experimental part, p. 6496 - 6511 (2010/10/02)
A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists.
Microbial deracemization of α-substituted carboxylic acids: Substrate specificity and mechanistic investigation
Kato, Dai-Ichiro,Mitsuda, Satoshi,Ohta, Hiromichi
, p. 7234 - 7242 (2007/10/03)
A new enzymatic method for the preparation of optically active α-substituted carboxylic acids is reported. This technique is called deracemization reaction, which provides us with a route to obtain the enantiomerically pure compounds, theoretically in 100% yield starting from the racemic mixture. This means that the synthesis of a racemate is almost equal to the synthesis of the optically active compound, and this concept is entirely different from the commonly accepted one in the asymmetric synthesis. Using the growing cell system of Nocardia diaphanozonaria JCM3208, racemates of 2-aryl- and 2-aryloxypropanoic acid are deracemized smoothly and (R)-form-enriched products are recovered in high chemical yield (>50%). In addition, using optically active starting compounds and deuterated derivatives as well as inhibitors, we have disclosed the fact that a new type of enzyme takes part in this biotransformation, and that the reaction proceeds probably via the same mechanism as that in rat liver.
