Atropoisomerismo: o efeito da quiralidade axial em substâncias bioativas

Química Nova

Anderson Rouge Dos Santos²  Alessandra Campbell Pinheiro²  Ana Carolina Rennó Sodero²  Andréa Sousa Da Cunha²  Monica Costa Padilha²  Priscila Mesquita De Sousa²  Silvia Paredes Fontes²  Márcia Paranho Veloso¹  Carlos Alberto Manssour Fraga¹ 

[1] ,Universidade Federal do Rio de Janeiro Instituto de Química Departamento de Química OrgânicaRio de Janeiro RJ ,Brasil

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

DOI  :  10.1590/S0100-40422007000100024

来源: SciELO

【 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】

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