96749-32-5Relevant academic research and scientific papers
N-Phenylbenzamide derivatives as alternative oxidase inhibitors: Synthesis, molecular properties, 1H-STD NMR, and QSAR
Barsottini, Mario R. O.,Carazzolle, Marcelo F.,Costa, Paulo C. S.,Evangelista, Joel S.,Miranda, Paulo C. M. L.,Nascimento, Andrey F. Z.,Pereira, Gon?alo A. G.,Pires, Bárbara A.,Rocco, Silvana A.,Sfor?a, Maurício L.,Silva, Jaqueline S.,Vieira, Maria L. L.,Zeri, Ana C. M.
, (2020/02/27)
In the present work, 117 N-phenylbenzamides (NPDs) were prepared and evaluated against recombinant AOX from the fungal pathogen Moniliophthora perniciosa. 1H, 13C NMR, FTIR, and mass spectra provided structural information on NPDs. The library compounds were tested as Alternative Oxidase inhibitors in two different assays using the model yeast Pichia pastoris: cell growth and oxygen consumption assays. The most active compound, 3FH, was further characterized by DRX and 1H-NMR-STD. Single crystal X-ray diffraction showed intra- and intermolecular interactions of 3FH in solid-state and elucidated its 3D structural configuration. 1H-NMR-STD allowed us to derive protein-ligand interactions in a membrane-mimetic system and evidenced an outstanding interaction of 3FH with this enzyme. Results of both biological assays were used as input to Quantitative Structure-Activity Relationship models, which highlighted the more important molecular fragments contributions for protein-ligand interaction.
Facile and Effective Synthesis of Unusually Substituted Aromatic N-Phenylamides
Kobs, Uwe,Neumann, Wilhelm P.
, p. 2191 - 2194 (2007/10/02)
A mild and effective new method for the preparation of a variety of arylamides 3a-i as well as heterocyclic 5a, b and 6 and olefinic amides 7, 9 is described.The reaction of trialkylstannyl-substituted aromatic, heterocyclic or vinylic hydrocarbons with aryl isocyanates in the presence of aluminium trichloride provides the corresponding N-aryl-substituted amides in good to excellent yields.The stannyl group serves as a powerful leaving group superior to hydrogen by several powers of ten which allows, via ipso substitution, to obtain isomer patterns not accessible by normal electrophilic substitution reactions, e. g. substitution in meta position with respect to a methoxy group.
