7433-86-5

Usage

InChI:InChI=1/C9H6N2O3/c12-10-6-8(11(13)14)5-7-3-1-2-4-9(7)10/h1-6H

Upstream product

• 1613-37-2 Quinoline N-oxide 
• 98-88-4 benzoyl chloride 
• 75-36-5 acetyl chloride 
• 17576-53-3 3-nitroquinoline 
• 540-80-7 tert.-butylnitrite 
• 91-22-5 quinoline 
• 67-66-3 chloroform 

Downstream Products

• 103029-75-0 3-Nitro-chinolin-2-ol 
• 580-17-6 3-aminoquinoline 
• 62141-03-1 1-oxy-quinolin-3-ylamine 
• 17576-53-3 3-nitroquinoline 
• 102170-61-6 3-nitroquinoline-2-carbonitrile 
• 1344663-94-0 3-nitro-2-phenylquinoline-1-oxide 
• 131459-07-9 1-benzoyloxy-3,6-dinitro-1H-quinolin-2-one 
• 52448-21-2 3-phenyl-3H-oxazolo[4,5-b]quinolin-2-one 
• 78105-39-2 2,3-diaminoquinoline 
• 102079-68-5 3,6-bis-acetylamino-1-benzoyloxy-1H-quinolin-2-one 

Relevant academic research and scientific papers

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).

Nitro-substituted quinoline nitrogen oxide derivative and preparation method thereof

The invention relates to a nitro-substituted quinoline nitrogen oxide derivative and a preparation method thereof. A structural formula of the nitro-substituted quinoline nitrogen oxide derivative is shown in a specification, wherein R1-R4 can be respectively and independently selected from hydrogen, halogen, alkyl group, alkyloxy group and phenyl group. The structure of the nitro-substituted quinoline nitrogen oxide derivative has a nitro group, can be taken as an organic synthesis intermediate, and has important application values in the fields of natural products, medical production and organic synthesis; and the compound has good application prospect for preparing antineoplastic medicines.

Structure-Activity Relationship for Small Molecule Inhibitors of Nicotinamide N-Methyltransferase

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.

Metal-free regioselective C-3 nitration of quinoline N-oxides with tert-butyl nitrite

A direct and eco-friendly nitration methodology to synthesize 3-nitroquinoline N-oxides from quinoline N-oxides using tert-butyl nitrite as both the nitro source and oxidant has been developed. Although this reaction undergoes a free radical process, it exhibits high regioselectivity and can be smoothly scaled up to gram scale. This journal is