54931-73-6Relevant academic research and scientific papers
Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones
Wang, Guanjie,Hu, Wanyao,Hu, Zhouli,Zhang, Yuxia,Yao, Wei,Li, Lin,Fu, Zhenqian,Huang, Wei
supporting information, p. 3302 - 3307 (2018/07/29)
A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.
Structure-Activity Relationship for Small Molecule Inhibitors of Nicotinamide N-Methyltransferase
Neelakantan, Harshini,Wang, Hua-Yu,Vance, Virginia,Hommel, Jonathan D.,McHardy, Stanton F.,Watowich, Stanley J.
, p. 5015 - 5028 (2017/06/28)
Nicotinamide N-methyltransferase (NNMT) is a fundamental cytosolic biotransforming enzyme that catalyzes the N-methylation of endogenous and exogenous xenobiotics. We have identified small molecule inhibitors of NNMT with >1000-fold range of activity and developed comprehensive structure-Activity relationships (SARs) for NNMT inhibitors. Screening of N-methylated quinolinium, isoquinolinium, pyrididium, and benzimidazolium/benzothiazolium analogues resulted in the identification of quinoliniums as a promising scaffold with very low micromolar (IC50 à 1 μM) NNMT inhibition. Computer-based docking of inhibitors to the NNMT substrate (nicotinamide)-binding site produced a robust correlation between ligand-enzyme interaction docking scores and experimentally calculated IC50 values. Predicted binding orientation of the quinolinium analogues revealed selective binding to the NNMT substrate-binding site residues and essential chemical features driving protein-ligand intermolecular interactions and NNMT inhibition. The development of this new series of small molecule NNMT inhibitors direct the future design of lead drug-like inhibitors to treat several metabolic and chronic disease conditions characterized by abnormal NNMT activity.
Heteroaromatic cation-based chromophores: Synthesis and nonlinear optical properties of Alkynylazinium salts
Caneque, Tatiana,Cuadro, Ana M.,Alvarez-Builla, Julio,Perez-Moreno, Javier,Clays, Koen,Marcelo, Gema,Mendicuti, Francisco,Castano, Obis,Andres, Jose L.,Vaquero, Juan J.
supporting information; experimental part, p. 6323 - 6330 (2011/01/13)
A variety of alkynylazinium cationic (D-π-A+) chromophores were prepared in good yields by the reaction of bromoazinium (pyridinium, quinolinium, and isoquinolinium iodides) with alkynes under Sonogashira conditions. The analysis of the experimentally recorded spectra is supported by quantum chemical calculations using restricted configuration interaction and density functional methods. First-order hyperpolarizabilities of (D-π-A +) azinium-based cations as a new class of second-order nonlinear optical (NLO) chromophores were also studied by hyper-Rayleigh scattering experiments and computational procedures. Copyright
