7477-46-5

Usage

InChI:InChI=1/C16H12N2O/c19-16(17-13-7-2-1-3-8-13)15-11-10-12-6-4-5-9-14(12)18-15/h1-11H,(H,17,19)

Upstream product

• 50342-01-3 quinolin-2-ylcarbonyl chloride 
• 62-53-3 aniline 
• 113640-32-7 quinoline-2-carboxylic acid-anhydride 
• 93-10-7 quinoline-2-carboxylic acid 
• 91-63-4 2-methylquinoline 
• 5603-13-4 (E)-N-(quinolin-2-ylmethylene)aniline 
• 91-22-5 quinoline 
• 500-72-1 oxanilic acid 
• 893769-45-4 8-(2-quinolinecarboxamido)quinoline 
• 5603-13-4 N-(quinolin-2-ylmethylidene)aniline 
• 5470-96-2 quinoline 2-carbaldehyde 
• 5378-52-9 phenyl-1H-tetrazole 

Downstream Products

• 1372806-63-7 N-(2-(trifluoromethyl)phenyl)quinoline-2-carboxamide 

Relevant academic research and scientific papers

Discovery of Potent Inhibitors of Streptococcus mutans Biofilm with Antivirulence Activity

Dental caries is a bacterial infectious disease characterized by demineralization of the tooth enamel. Treatment of this disease with conventional antibiotics is largely ineffective as the cariogenic bacteria form tenacious biofilms that are resistant to such treatments. The main etiological agent for dental caries is the bacterium Streptococcus mutans. S. mutans readily forms biofilms on the tooth surface and rapidly produces lactic acid from dietary sucrose. Glucosyl transferases (Gtfs) secreted by S. mutans are mainly responsible for the production of exopolysaccharides that are crucial for the biofilm architecture. Thus, inhibiting S. mutans' Gtfs is an effective approach to develop selective biofilm inhibitors that do not affect the growth of oral commensals. Herein, we report a library of 90 analogs of the previously identified lead compound, G43, and exploration of its structure activity relationships (SAR). All compounds were evaluated for the inhibition of S. mutans biofilms and bacterial growth. Selected compounds from this library were further evaluated for enzyme inhibition against Gtfs using a zymogram assay and for growth inhibition against oral commensal bacterial species such as Streptococcus gordonii and Streptococcus sanguinis. This study has led to the discovery of several new biofilm inhibitors with enhanced potency and selectivity. One of the leads, IIIF1, showed marked reduction in buccal, sulcal, and proximal caries scores in a rat model of dental caries.

A metal-free picolinamide assisted electrochemical ortho-trifluoromethylation of arylamines

An eco-friendly and effective electrochemical process was developed for the ortho-trifluoromethylation of arylamines using CF3SO2Na as the trifluoromethyl source, affording the desired products in moderate to good yields with high regioselectivity under mild reaction conditions. Importantly, the requirement for both transition metals and oxidants utilized in previous methods were avoided. A radical mechanism was proposed on the basis of various control experiments.

Silver-catalyzed direct C-H oxidative carbamoylation of quinolines with oxamic acids

A silver-catalyzed efficient and direct C-H carbamoylation of quinolines with oxamic acids to access carbamoylated quinolines has been developed through oxidative decarboxylation reaction. The reaction proceeds smoothly over a broad range of substrates wi

An efficient, one-pot transamidation of 8-aminoquinoline amides activated by tertiary-butyloxycarbonyl

The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C(acyl)–N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields.

Iron-catalyzed: Ortho trifluoromethylation of anilines via picolinamide assisted photoinduced C-H functionalization

A convenient, oxidant-free protocol was developed for the ortho trifluoromethylation of aniline via picolinamide assisted Fe-promoted C-H functionalization under ultraviolet irradiation. In this transformation acetone essentially acted as both a solvent to dissolve reactants and a low-cost radical initiator to efficiently generate a CF3 radical from Langlois' reagent. A broad substrate scope was tolerated and picolinamide bearing strong electron withdrawing groups also could be transformed into the corresponding products with acceptable yields. Furthermore, the value of this method has been highlighted via the efficient synthesis of the nonsteroidal anti-inflammatory drug floctafenine.

Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary Amines

Electrochemical oxidation represents an environmentally friendly solution to conventional methods that require caustic stoichiometric chemical oxidants. However, C-H functionalizations merging transition-metal catalysis and electrochemical techniques are, to date, largely confined to the use of precious metals and divided cells. Herein, we report the first examples of copper-catalyzed electrochemical C-H aminations of arenes at room temperature using undivided electrochemical cells, thereby providing a practical solution for the construction of arylamines. The use of n-Bu4NI as a redox mediator is crucial for this transformation. On the basis of mechanistic studies including kinetic profiles, isotope effects, cyclic voltammetric analyses, and radical inhibition experiments, the reaction appears to proceed via a single-electron-transfer (SET) process, and a high valent Cu(III) species is likely involved. These findings provide a new avenue for transition-metal-catalyzed electrochemical C-H functionalization reactions using redox mediators.

A two-stage, three-stage aromatic amide compound synthesis method

The invention provides a synthetic method for forming binary and ternary aryl amide compounds by virtue of direct methyl functionalization. The method comprises the following steps: by taking a 2-methyl-N-heterocyclic aromatic hydrocarbon and an amine sou

Development of Novel 1,2,3,4-Tetrahydroquinoline Scaffolds as Potent NF-κB Inhibitors and Cytotoxic Agents

1,2,3,4-Tetrahydroquinolines have been identified as the most potent inhibitors of LPS-induced NF-κB transcriptional activity. To discover new molecules of this class with excellent activities, we designed and synthesized a series of novel derivatives of 1,2,3,4-tetrahydroquinolines (4a-g, 5a-h, 6a-h, and 7a-h) and bioevaluated their in vitro activity against human cancer cell lines (NCI-H23, ACHN, MDA-MB-231, PC-3, NUGC-3, and HCT 15). Among all synthesized scaffolds, 6g exhibited the most potent inhibition (53 times that of a reference compound) of LPS-induced NF-κB transcriptional activity and the most potent cytotoxicity against all evaluated human cancer cell lines.

Copper-catalyzed efficient direct amidation of 2-methylquinolines with amines

A novel Cu-catalyzed direct amidation of 2-methylquinolines with amines is described. This method afforded an efficient approach for the synthesis of biologically important aromatic amides from readily available coupling partners using molecular oxygen as the oxidant.

Copper catalysed direct amidation of methyl groups with N-H bonds

An efficient copper catalyzed direct aerobic oxidative amidation of methyl groups of azaarylmethanes with N-H bonds producing amides is successfully developed, which can produce primary, secondary and tertiary amides, including those with functional groups. This reaction represents a straightforward method for the preparation of amides from the readily available hydrocarbon starting materials.