593279-83-5Relevant academic research and scientific papers
Conformational analysis of N→BH3, N→BF3, and N-CH3 + complexes with ibuprofen-derivative amides
Romero-Chávez, Maria M.,Pineda-Urbina, Kayim,Maga?a-Vergara, Nancy E.,Vázquez-Cárdenas, Rubén,Gómez-Sandoval, Zeferino,Ramos-Organillo, ángel
, (2017/06/27)
The synthesis and structural characterization of novel amine-borane adducts of ibuprofen derivatives are presented. The changes of the electron density on the carbonyl and pyridine ring after formation of N→BH3, N→BF3, and N-CH3 + have been confirmed by 1H, 11B, 13C, and 19F NMR, further supported by homonuclear and heteronuclear correlations. Moreover, electrostatic interactions —H+···?F and the nonclassical H+···?H— were identified by NMR spectra. The analysis of the resulting molecular structures offered insights on the 2-aminopyridine N→B adducts. The N→BH3 adduct formed a single molecular arrangement, both in C6D6 and CDCl3. The same behavior was observed for the N→BF3 adduct in CDCl3. However, two conformers of this adduct were detected in C6D6. All adduct geometries were corroborated by density functional theory computational calculations.
2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors
Allegretti, Marcello,Bertini, Riccardo,Cesta, Maria Candida,Bizzarri, Cinzia,Di Bitondo, Rosa,Di Cioccio, Vito,Galliera, Emanuela,Berdini, Valerio,Topai, Alessandra,Zampella, Giuseppe,Russo, Vincenzo,Di Bello, Nicoletta,Nano, Giuseppe,Nicolini, Luca,Locati, Massimo,Fantucci, Piercarlo,Florio, Saverio,Colotta, Francesco
, p. 4312 - 4331 (2007/10/03)
The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCLS-induced human PMNs chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.
Synthesis of ibuprofen heterocyclic amides and investigation of their analgesic and toxicological properties
Cocco, Maria Teresa,Congiu, Cenzo,Onnis, Valentina,Morelli, Micaela,Cauli, Omar
, p. 513 - 518 (2007/10/03)
A series of amides of ibuprofen with heteroaromatic amines was synthesized and assayed in vivo for their analgesic properties by means of writhing test in rats. When compared to parent ibuprofen some of the new amides exhibited a comparable or improved an
