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- Title
Late‐Stage Functionalization by Chan–Lam Amination: Rapid Access to Potent and Selective Integrin Inhibitors.
- Authors
Robinson, Henry; Oatley, Steven A.; Rowedder, James E.; Slade, Pawel; Macdonald, Simon J. F.; Argent, Stephen P.; Hirst, Jonathan D.; McInally, Thomas; Moody, Christopher J.
- Abstract
A late‐stage functionalization of the aromatic ring in amino acid derivatives is described. The key step is a copper‐catalysed diversification of a boronate ester by amination (Chan–Lam reaction) that can be carried out on a complex β‐aryl‐β‐amino acid scaffold. This not only considerably extends the substrate scope of amination partners, but also delivers an array of potent and selective integrin inhibitors as potential treatment agents of idiopathic pulmonary fibrosis (IPF). This versatile chemical strategy, which is amenable to high‐throughput‐array protocols, allows the installation of pharmaceutically valuable heteroaromatic fragments at a late stage by direct coupling to NH heterocycles, leading to compounds with drug‐like attributes. It thus constitutes a useful addition to the medicinal chemist's repertoire.
- Subjects
AMINO acid derivatives; IDIOPATHIC pulmonary fibrosis; AMINATION; BORONIC esters; INTEGRINS
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 34, p7678
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.202001059