17193-40-7Relevant articles and documents
Efficient Multikilogram Synthesis of a VLA-4 Antagonist via a Povarov Reaction
Cerfontaine, Patrick,Driessens, Frank,Deltent, Marie-France,Petit, Sylvain
, p. 807 - 816 (2019/12/24)
Herein we describe the practical synthesis of a novel VLA-4 antagonist 1 as a potential treatment for multiple sclerosis. The key step is based on the Povarov reaction of an imine with an alkene to access a tetrahydroquinoline intermediate, leading to the corresponding quinoline core after an oxidative aromatization step. The development of the synthesis of 1 led to decreased complexity and the elimination of chromatographic purifications. These improvements were demonstrated at scale by the production of 32 kg of 1 in high yield with excellent purity.
Tuning the reaction pathways of phenanthroline-Schiff bases: Routes to novel phenanthroline ligands
Ahmed, Muhib,Rooney, Denise,McCann, Malachy,Casey, Jamie,O'Shea, Katie,Twamley, Brendan
, p. 15283 - 15289 (2019/10/22)
Pyrido-phenanthrolin-7-one compounds are structural analogues of the cytotoxic alkaloid, ascididemin, and would be expected to have interesting biological activities. Synthetic strategies are reported for a novel simple route to form this class of ligand. 1,10-Phenanthrolin-5,6-dione reacts with l-phenylalanine alkyl esters and their para-substituted analogues to form both a phenanthroline-oxazine and a pyrido-phenanthrolin-7-one product. The nature of the major product is dependent on the electronic properties of the para substituent. Successful metal coordination to the pyrido-phenanthrolin-7-one ligand is also presented.
An Optically Active Polymer for Broad-Spectrum Enantiomeric Recognition of Chiral Acids
Yan, Jijun,Kang, Chuanqing,Bian, Zheng,Ma, Xiaoye,Jin, Rizhe,Du, Zhijun,Gao, Lianxun
supporting information, p. 5824 - 5829 (2017/04/28)
Recognition of enantiomers of chiral acids by anion–π or lone pair–π interactions has not yet been investigated but is a significant and attractive challenge. This study reports an optically active polymer-based supramolecular system with capabilities of discriminating enantiomers of various chiral acids. The polymer featuring alternate π-acidic naphthalenediimides (NDIs) and methyl l-phenylalaninates in the backbone exhibits an unprecedented slow self-assembly process that is susceptible to perturbation by various chiral acids. Thus, the combination of anion–π or lone pair–π interactions and sensitivity of the polymeric self-assembly process to external chiral species endows the system with recognition capabilities. This is the first time that anion–π or lone pair–π interactions have been applied in the recognition of enantiomers of various chiral acids with a single system. The results shed light on new strategies for material design by integrating π-acidic aromatic systems and chiral building blocks to afford relevant advanced functions.