Atropisomerism in the pharmaceutically relevant realm

M Basilaia, MH Chen, J Secka… - Accounts of Chemical …, 2022 - ACS Publications
Conspectus Atropisomerism is a conformational chirality that occurs when there is hindered
rotation about a σ-bond. While atropisomerism is exemplified by biaryls, it is observed in …

Assessing atropisomer axial chirality in drug discovery and development

SR LaPlante, LD Fader, KR Fandrick… - Journal of medicinal …, 2011 - ACS Publications
An underlying goal of drug discovery is to develop safe and stable substances that
specifically target essential elements that cause disease. Molecular chirality adds an …

Recent advances in catalytic asymmetric construction of atropisomers

JK Cheng, SH Xiang, S Li, L Ye, B Tan - Chemical Reviews, 2021 - ACS Publications
Atropisomerism is a stereochemical behavior portrayed by three-dimensional molecules that
bear rotationally restricted σ bond. Akin to the well-represented point-chiral molecules …

Recent encounters with atropisomerism in drug discovery

PW Glunz - Bioorganic & medicinal chemistry letters, 2018 - Elsevier
Atropisomerism is stereochemistry arising from restricted bond rotation that creates a chiral
axis. Atropisomers are subject to time-dependent inversion of chirality via bond rotation, a …

Atropisomerism in medicinal chemistry: challenges and opportunities

ST Toenjes, JL Gustafson - Future medicinal chemistry, 2018 - Taylor & Francis
Atropisomerism is a dynamic type of axial chirality that is ubiquitous in medicinal chemistry.
There are several examples of stable atropisomeric US FDA-approved drugs and …

[HTML][HTML] Atropisomers: synthesis, analysis, and applications

MC Kozlowski, SJ Miller, S Perreault - Accounts of Chemical …, 2023 - ACS Publications
A modern course of stereochemistry might shock Louis Pasteur, Jacobus Henricus van't
Hoff, Joseph Lebel, Lord Kelvin, Charlotte Finch Roberts, and many other pioneers of the …

Exploiting atropisomerism to increase the target selectivity of kinase inhibitors

DE Smith, I Marquez, ME Lokensgard… - Angewandte …, 2015 - Wiley Online Library
Many biologically active molecules exist as rapidly interconverting atropisomeric mixtures.
Whereas one atropisomer inhibits the desired target, the other can lead to off‐target effects …

Approaches to Synthesis and Isolation of Enantiomerically Pure Biologically Active Atropisomers

ACC Carlsson, S Karlsson, RH Munday… - Accounts of Chemical …, 2022 - ACS Publications
Conspectus Atropisomerism is a stereochemical phenomenon exhibited by molecules
containing a rotationally restricted σ bond. Contrary to classical point chirality, the two …

Enantioselective strategies for the synthesis of N− N atropisomers

G Centonze, C Portolani, P Righi… - Angewandte …, 2023 - Wiley Online Library
Axially chiral compounds have been always considered a laboratory curiosity with rare
prospects of being applied in asymmetric synthesis. Things have changed very quickly in the …

Atropisomerism in drug discovery: a medicinal chemistry perspective inspired by atropisomeric class I PI3K inhibitors

S Perreault, J Chandrasekhar… - Accounts of Chemical …, 2022 - ACS Publications
Conspectus Atropisomerism is a type of axial chirality resulting from hindered rotation about
a σ bond that gives rise to nonsuperimposable stereoisomers (termed “atropisomers”). The …