93531-06-7Relevant articles and documents
Cinchona alkaloid derivative modified Fe3O4nanoparticles for enantioselective ring opening of: Meso -cyclic anhydrides
Soni, Hemant P.,Tomer, Sanjiv O.
, p. 2495 - 2507 (2022/02/11)
In the present work, the molecular framework of quinidine was modified at the methoxy functional group of the C6′ carbon of the quinoline moiety with a long-chain carboxylic acid group (-COOH) and it was used as a capping agent during the synthesis of Fe3
Pre-organization of the core structure of E-selectin antagonists
Schwizer, Daniel,Patton, John T.,Cutting, Brian,Smiesko, Martin,Wagner, Beatrice,Kato, Ako,Weckerle, Celine,Binder, Florian P. C.,Rabbani, Said,Schwardt, Oliver,Magnani, John L.,Ernst, Beat
, p. 1342 - 1351 (2012/04/04)
A new class of N-acetyl-dglucosamine (GlcNAc) mimics for Eselectin antagonists was designed and synthesized. The mimic consists of a cyclohexane ring substituted with alkyl substituents adjacent to the linking position of the fucose moiety. Incorporation into E-selectin antagonists led to the test compounds 8 and the 2'-benzoylated analogues 21, which exhibit affinities in the low micromolar range. By using saturation transfer difference (STD)-NMR it could be shown that the increase in affinity does not result from an additional hydrophobic contact of the alkyl substituent with the target protein E-selectin, but rather from a steric effect stabilizing the antagonist in its bioactive conformation. The loss of affinity found for antagonists 10 and 35 containing a methyl substituent in a remote position (and therefore unable to support to the stabilization of the core) further supports this hypothesis. Finally, when a GlcNAc mimetic containing two methyl substituents (52 and 53) was used, in which one methyl was positioned adjacent to the fucose linking position and the other was in a remote position, the affinity was regained.
Highly enantioselective desymmetrization of meso anhydrides by a bifunctional thiourea-based organocatalyst at low catalyst loadings and room temperature
Peschiulli, Aldo,Gun'ko, Yurii,Connon, Stephen J.
, p. 2454 - 2457 (2008/09/19)
(Chemical Equation Presented) Bifunctional (thio)urea-based cinchona alkaloid derivatives have been shown to promote highly efficient enantioselective desymmetrization reactions of meso anhydrides. The most selective of these catalysts is capable of the enantioselective methanolysis of succinic and glutaric anhydride derivatives to form hemiester products with >90% yield and enantiomeric excess at 1 mol % loading and ambient temperature.
