Atropisomerism: the effect of the axial chirality in bioactive compounds

Química Nova

Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brasil¹  Veloso, Márcia Paranho¹  Santos, Anderson Rouge dos¹  Fontes, Silvia Paredes¹  Universidade Federal de Alfenas, Alfenas, Brasil¹  Padilha, Monica Costa¹  Sousa, Priscila Mesquita de¹  Cunha, Andréa Sousa da¹  Fraga, Carlos Alberto Manssour¹  Pinheiro, Alessandra Campbell¹  Sodero, Ana Carolina Rennó¹ 

关键词: atropisomerism;    atropisomerism of drugs;    stereoselective molecular recognition.;   

DOI  :  10.1590/S0100-40422007000100024

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

Atropisomerism is a special kind of stereoisomeric relationship that arises from the freezing of a certain conformation of an organic molecule, associated with a high rotational barrier about a single covalent bond. Atropisomerism has been originally described in orto-functionalyzed biphenyl derivatives, but a lot of other organic functionalities can present this structural phenomenon, characterized by the presence of chiral properties in compounds that don't present classical stereogenic centers. Atropisomeric compounds, intermediates and catalysts have well-know importance in organic synthesis, but the influence of the axial chirality in substances able to modulate biological systems is still not very exploited in drug design and development. In this context, the present account describes the importance of this structural property in the medicinal chemistry of different classes of bioactive compounds or therapeutic agents, emphasizing how atropisomerism could affect the molecular recognition of a ligand or a prototype by the target bioreceptor.

【 授权许可】

Unknown