130406-30-3Relevant articles and documents
Resolution of N-Protected amino alcohols by porcine pancreatic lipase
Magrioti, Victoria,Fotakopoulou, Irene,Athinaios, Nicolaos,Anastasopoulou, Panoula,Constantinou-Kokotou, Violetta,Kokotos, George
scheme or table, p. 159 - 162 (2010/08/19)
The resolution of 2-amino alcohols protected by urethane-type groups either via porcine pancreatic lipase (PPL) hydrolysis of the corresponding racemic acetates or via PPL catalyzed transesterification of racemic alcohols was studied. In both cases, Boc protecting group led to better chemical yields and enantiopurities than Z and Fmoc protecting groups. Furthermore, a simple and efficient method for the synthesis of the medicinally interesting optically pure (R)-2- aminohexadecanol was developed.
Asymmetric synthesis of highly substituted azapolycyclic compounds via 2-alkenyl sulfoximines: Potential scaffolds for peptide mimetics
Reggelin, Michael,Junker, Bernd,Heinrich, Timo,Slavik, Stefan,Buehle, Philipp
, p. 4023 - 4034 (2007/10/03)
The application of metalated, enantiomerically pure acyclic and cyclic 2-alkenyl sulfoximines for the synthesis of highly substituted aza(poly)cyclic ring systems is described. The method relies on a one-pot combination of a reagent-controlled allyl transfer reaction to α- or β-amino aldehydes, followed by a Michael-type cyclization of the intermediate vinyl sulfoximines generated in the first step. The sulfur-free target compounds are preferentially obtained by samarium iodide treatment of the sulfonimidoyl substituted heterocycles. In addition to this methodological work, initial results on the biological activity of selected examples are reported. Furthermore, a concept for the transformation of peptidic lead structures into non-peptide mimetics is described, and the relevance of the new approach to highly substituted azaheterocycles in this context is discussed.
Rationally Designed "Dipeptoid" Analogues of CCK. α-Methyltryptophan Derivatives as Highly Selective and Orally Active Gastrin and CCK-B Antagonists with Potent Anxiolytic Properties
Horwell, David C.,Hughes, John,Hunter, John C.,Pritchard, Martyn C.,Richardson, Reginald S.,at al.
, p. 404 - 414 (2007/10/02)
This paper describes the synthesis and structure-activity relationships (SAR) leading to the first rational design of "dipeptoid" analogues of the neuropeptide cholecystokinin (CCK).Compounds *,S*)>-4-2-3-(1H-indol-3-yl)-2-m
