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Synthesis and characterization of the atropisomeric relationships of a substituted N ‐phenyl‐bipyrazole derivative with anti‐inflammatory properties
Author(s) -
Veloso Marcia P.,
Romeiro Nelilma C.,
Silva Gilberto M. S.,
Alves Hélio De M.,
Doriguetto Antonio C.,
Ellena Javier,
Miranda Ana L. P.,
Barreiro Eliezer J.,
Fraga Carlos A. M.
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22016
Subject(s) - chemistry , atropisomer , derivative (finance) , amine gas treating , salt (chemistry) , chiral column chromatography , stereochemistry , organic chemistry , high performance liquid chromatography , financial economics , economics
This work describes the atropisomeric relationships of 3‐methyl‐5‐(3‐methyl‐5‐phenyl‐1 H ‐pyrazol‐1‐yl)‐1‐phenyl‐1 H ‐pyrazol‐4‐amine ( 2d ), which belongs to series 4‐aminobipyrazole derivatives designed as anti‐inflammatory agents. The 1 H nuclear magnetic resonance spectra obtained in the presence of a chiral lanthanide shift salt associated to chiral high‐performance liquid chromatography analysis, X‐ray diffraction, and molecular modeling tools confirmed that ortho bis‐functionalized bipyrazole 2d exists as a mixture of aR , aS ‐atropisomers. These results provide useful information to understand the pharmacological profile of this derivative and of other 4‐aminobipyrazole analogs. Chirality 24:463–470, 2012. © 2012 Wiley Periodicals, Inc.