18543-22-1Relevant articles and documents
Competing HB acceptors: An extensive NMR investigations corroborated by single crystal XRD and DFT calculations
Tiwari, Surbhi,Arya, Neeru,Mishra, Sandeep Kumar,Suryaprakash
, p. 15195 - 15202 (2021/05/21)
A series of N-benzoylanthranilamide derivatives have been synthesized with the substitution of competitive HB acceptors and investigated by NMR spectroscopy and single crystal XRD. The interesting rivalry for HB acceptance between CO and X (F or OMe) is observed in the investigated molecules which leads to an unusual increase in the electron density at the site of one of the NH protons, reflecting in the high field resonance in the 1H NMR spectrum. The NMR experimental findings and single crystal XRD are further reinforced by the DFT studies.
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.
Domino synthesis of pyrimido and imidazoquinazolinones
Fathalla, Walid,Nofal, Eman Y.,El-Moneim, Mohamed Abd
, p. 1266 - 1274 (2020/01/21)
A simple method for the synthesis of N-alkyl-2-arylquinazolin-4-amines, methyl 4-((2-arylquinazolin-4-yl)amino) butanoates, 6-aryl-2,3-dihydro-4H-pyrimido[1,2-c]quinazolin-4-ones, and 5-arylimidazo[1,2-c]quinazolin-3(2H)-ones has been described. It involves a simple reaction of N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides with alkylamine, γ-aminobutyric acid, β-alanine, l-alanine, and glycine methyl esters hydrochloride in acetonitrile to afford the desired compounds after a series of instantaneous reactions that include Dimroth rearrangement. The reaction involves reflux for 12 hours, simple addition of reagents to an in situ generated benzimidoyl chloride, and simple workup, to form 21 examples of pure compounds in high yields. The active intermediate N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides were formed by the reaction of N-(2-cyanophenyl)-substitutedbenzamides with thionyl chloride in a one-pot strategy. The alternative method described for this preparation deals with an exhausting multistep reactions starting from anthranilic acid.
