42762-51-6Relevant articles and documents
Efficient Dimerization Disruption of Leishmania infantum Trypanothione Reductase by Triazole-phenyl-thiazoles
Revuelto, Alejandro,De Lucio, Héctor,García-Soriano, Juan Carlos,Sánchez-Murcia, Pedro A.,Gago, Federico,Jiménez-Ruiz, Antonio,Camarasa, María-José,Velázquez, Sonsoles
supporting information, p. 6137 - 6160 (2021/05/29)
Inhibition of Leishmania infantum trypanothione disulfide reductase (LiTryR) by disruption of its homodimeric interface has proved to be an alternative and unexploited strategy in the search for novel antileishmanial agents. Proof of concept was first obtained by peptides and peptidomimetics. Building on previously reported dimerization disruptors containing an imidazole-phenyl-thiazole scaffold, we now report a new 1,2,3-triazole-based chemotype that yields noncompetitive, slow-binding inhibitors of LiTryR. Several compounds bearing (poly)aromatic substituents dramatically improve the ability to disrupt LiTryR dimerization relative to reference imidazoles. Molecular modeling studies identified an almost unexplored hydrophobic region at the interfacial domain as the putative binding site for these compounds. A subsequent structure-based design led to a symmetrical triazole analogue that displayed even more potent inhibitory activity over LiTryR and enhanced leishmanicidal activity. Remarkably, several of these novel triazole-bearing compounds were able to kill both extracellular and intracellular parasites in cell cultures.
The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide
Lifchits, Olga,Mahlau, Manuel,Reisinger, Corinna M.,Lee, Anna,Fares, Christophe,Polyak, Iakov,Gopakumar, Gopinadhanpillai,Thiel, Walter,List, Benjamin
supporting information, p. 6677 - 6693 (2013/06/05)
Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.
Straightforward access to α-methylamines through cross-metathesis
Poulhes, Florent,Sylvain, Remy,Perfetti, Patricia,Bertrand, Michele P.,Gil, Gerard,Gastaldi, Stephane
experimental part, p. 1334 - 1338 (2010/07/06)
A two-step procedure involving cross-metathesis and reductive amination enables easy access to -methylamines and α,α′-dimethyldiamines from a wide variety of terminal olefins. Georg Thieme Verlag Stuttgart · New York.
