51135-38-7Relevant articles and documents
Conformational and crystal energetics of a polymorphic cyclized product of Napafenac: The Z′ and crystal stability correlation
Nanubolu, Jagadeesh Babu,Ravikumar, Krishnan,Sridhar, Balasubramanian,Sreedhar, Bojja
, p. 133 - 145 (2014)
We report the single crystal diffraction study of a dimorphic 7-benzoyl-1,3-dihydroindol-2-one system and evaluate its stability relationships through thermal, grinding and slurry methods. Computational methods are invoked to understand the stability relationships. The form I crystallizes in the triclinic space group P1ˉ with two molecules in the asymmetric unit (Z′ = 2), whereas, form II crystallizes in the monoclinic space group P21/c with a single molecule in the asymmetric unit (Z′ = 1). The molecules exhibit subtle conformational variations along the bond connecting the phenyl and indole rings and adopt different crystal packing. While both polymorphs show similar amide dimer of NH?O interactions, they do differ significantly in the way the amide dimers are packed. The Differential Scanning Calorimetry (DSC), phase transformation studies and lattice energy calculations clearly established the greater stability of high Z′ form over low Z′ form, which contradicts the widely accepted notion that Z′ > 1 structures are usually kinetic (or metastable). The choice of two different orientations of phenyl rings in form I enforces shorter π?π interactions and additional CH?π contacts to result in the extra stabilization energy over form II crystal packing with a single conformer. The Z′ and stability correlation is established in 83 reported polymorphic systems which indicate that the number of stable crystal structures decrease as the Z′ value increases. However, the polymorphic systems with Z′ = 1 and 2 combinations are more frequently observed than any other combinations.
Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles
Chen, Jiuxi,Ye, Leping,Su, Weike
supporting information, p. 8204 - 8211 (2015/01/08)
A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L-1 and 0.09 μmol L-1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L-1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target. This journal is
Antiinflammatory Agents. 2. Syntheses and Antiinflammatory Activity of Substituted 2-Aminophenylacetic Acid Derivatives
Walsh, David A.,Shamblee, Dwight A.,Welstead, William J.,Sancilio, Lawrence F.
, p. 446 - 451 (2007/10/02)
Several substituted 2-aminophenylacetic acid derivatives were prepared and tested for in vitro prostaglandin synthetase inhibition and for in vivo antiinflammatory activity.The 2-amino substituent is beneficial to potency in the inhibition of prostaglandin synthetase for the 3-phenoxy, 4-phenyl, and 3-benzoyl series, but only 3-benzoyl series shows increased antiinflammatory potency in the in vivo assay.
