title: Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties.
abstract: This work describes the atropisomeric relationships of 3-methyl-5-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1-phenyl-1H-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.
authors.affiliation: Laboratório de Avaliação e Síntese de Substâncias Bioativas (LASSBio), Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brazil.
authors.forename: Marcia P
authors.initials: MP
authors.lastname: Veloso
authors.forename: Nelilma C
authors.initials: NC
authors.lastname: Romeiro
authors.forename: Gilberto M S
authors.initials: GM
authors.lastname: Silva
authors.forename: Hélio De M
authors.initials: Hde M
authors.lastname: Alves
authors.forename: Antonio C
authors.initials: AC
authors.lastname: Doriguetto
authors.forename: Javier
authors.initials: J
authors.lastname: Ellena
authors.forename: Ana L P
authors.initials: AL
authors.lastname: Miranda
authors.forename: Eliezer J
authors.initials: EJ
authors.lastname: Barreiro
authors.forename: Carlos A M
authors.initials: CA
authors.lastname: Fraga
mesh_terms: D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D011485:Protein Binding / Q000187:drug effects; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000893:Anti-Inflammatory Agents; D011720:Pyrazoles; C031280:pyrazole