2623-50-9

Usage

InChI:InChI=1/C11H11N/c1-8-5-6-9(2)11-10(8)4-3-7-12-11/h3-7H,1-2H3

Upstream product

• 95-78-3 2,5-Dimethylaniline 
• 56-81-5 glycerol 
• 156-87-6 propan-1-ol-3-amine 

Downstream Products

• 74316-52-2 8-methyl-5-quinolinecarboxylic acid 
• 557-30-2 glyoxime 
• 117194-01-1 8-methyl-pyrido[2,3-d][1,2]oxazin-5-one 
• 16174-40-6 2,3-Diacetylpyridin 

Relevant academic research and scientific papers

Chemosensing of Guanosine Triphosphate Based on a Fluorescent Dinuclear Zn(II)-Dipicolylamine Complex in Water

Guanosine triphosphate (GTP) is a key biomarker of multiple cellular processes and human diseases. The new fluorescent dinuclear complex [Zn2(L)(S)][OTf]4, 1 (asymmetric ligand, L = 5,8-Bis{[bis(2-pyridylmethyl)amino] methyl}quinoline, S = solvent, and OTf = triflate anion) was synthesized and studied in-depth as a chemosensor for nucleoside polyphosphates and inorganic anions in pure water. Additions at neutral pH of nucleoside triphosphates, guanosine diphosphate, guanosine monophosphate, and pyrophosphate (PPi) to 1 quench its blue emission (λem = 410 nm) with a pronounced selectivity toward GTP over other anions, including adenosine triphosphate (ATP), uridine triphosphate (UTP), and cytidine triphosphate (CTP). The efficient quenching response by the addition of GTP was observed in the presence of coexisting species in blood plasma and urine with a detection limit of 9.2 μmol L-1. GTP also shows much tighter binding to the receptor 1 on a submicromolar level. On the basis of multiple spectroscopic tools (1H, 31P NMR, UV-vis, and fluorescence) and DFT calculations, the binding mode is proposed through three-point recognition involving the simultaneous coordination of the N7 atom of the guanosine motif and two phosphate groups to the two Zn(II) atoms. Spectroscopic studies, MS-ESI, and DFT suggested that GTP bound to 1 in 1:1 and 2:2 models with high overall binding constants of log β1 (1:1) = 6.05 ± 0.01 and log β2 = 10.91 ± 0.03, respectively. The optical change and selectivity are attributed to the efficient binding of GTP to 1 by the combination of a strong electrostatic contribution and synergic effects of coordination bonds. Such GTP selectivity of an asymmetric metal-based receptor in water is still rare.

RhIII-Catalyzed Direct Heteroarylation of C(sp3)-H and C(sp2)-H Bonds in Heterocycles with N-Heteroaromatic Boronates

Herein, we disclose a RhIII-catalyzed heteroarylation of C(sp3)-H and C(sp2)-H bonds in heterocycles with organoboron reagents. This protocol displays high efficiency and excellent functional group tolerance. A range of heterocyclic boronates with strong coordinating atoms, including pyridine, pyrimidine, pyrazole, thiophene, and furan derivatives, can be extensively served as the coupling reagents. The direct heteroarylation method could supply potential application in terms of the synthesis of drug molecules with multiple heterocycles.

Recognition and visual detection of ADP and ATP based on a dinuclear Zn(II)-complex with pyrocatechol violet in water

The new fluorescent dinuclear complex [Zn2L(S)] 1, (asymmetric ligand, L = 5,8-Bis{[bis(acetate)amino]methyl} quinoline, S = solvent) was synthesized and studied in-depth as a receptor for nucleoside polyphosphates in 100% aqueous solution at physiological pH. The Zn-receptor 1 shows turn-on fluorescence and high selectivity to adenosine 5′-diphosphate (ADP) and adenosine 5′-triphosphate (ATP) over other phosphorylated anions including guanosine 5′-tripohosphate (GTP), citidine 5′-tripohosphate (CTP) and pyrophosphate. On the basis of the spectroscopic tools (1H, 31P NMR, UV–vis, fluorescence) and DFT calculations, the Zn-receptor binds ADP with high affinity (log K = 5.12) through three-point recognition involving cooperative coordination bonds and a hydrogen bond. The Zn-receptor 1 is an order of the magnitude more selective for ADP than ATP. ADP can be selectively detected in water even in the presence of coexisting species in blood plasma and urine with a detection limit of 30 μmol L?1 using a naked-eye detection system based on the complex between Zn-receptor 1 and pyrocatechol violet.

Cobalt-catalyzed ring-opening addition of azabenzonorbornadienes: Via C(sp3)-H bond activation of 8-methylquinoline

The first ring-opening addition of a benzylic C(sp3)-H bond to azabenzonorbornadienes is demonstrated. The reaction proceeded under the catalytic system of [Cp?CoI2(CO)], AgSbF6 and Fe(OAc)2 in PhOMe. The methodology showed a good substrate scope with up to 96 yield. The relative configuration of the product was determined as cis-configuration by X-ray crystallography.

Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation

The rhodium(III)-catalyzed coupling of C-H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C-H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol % in a gram-scale reaction. Representative products exhibit cytotoxicity toward human cancer cells at nanomolar levels.

PD-1/PD-L1 small-molecule inhibitor and preparation method and application thereof

The invention discloses a PD-1/PD-L1 small-molecule inhibitor and a preparation method and application thereof. Specifically, the invention discloses a compound with the structure shown in the formulaL, a stereoisomer or a tautomer thereof, or pharmaceutically acceptable salts or hydrates or solvates thereof, and please see the specification for specific definitions. The compound has excellent effects for restraining PD-1/PD-L1. Please see the specification for the formula.

Rh(iii)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds

A straightforward Rh(iii)-catalyzed general strategy was developed for the introduction of naphthol/phenol moieties to the C(sp3)-H bond of 8-methylquinoline using diazonaphthalen-2(1H)-ones/quinone diazides. The developed method was further extended towards the arylation of 8-formylquinolines to accomplish diarylketone derivatives. The method is simple, relatively rapid, and chemo and regioselective with a wide scope and functional group tolerance. The synthetic utility was established through gram-scale synthesis and biologically active molecule construction.

Palladium-Catalyzed C-H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents

A new and operationally simple approach for palladium-catalyzed C-H functionalization reactions utilizing an organophosphorus/sulfonate hypervalent iodine reagent as both an oxidant and the source of a functional group has been developed. Through this method, the oxidative phosphorylation-, sulfonation-, and hydroxylation of unactivated benzyl C(sp3)-H bonds, along with the hydroxylation and arylation of aryl C(sp2)-H bonds, are successfully realized under mild conditions and with excellent site-selectivity. The versatile C-OSO2R bond provides a platform for a wide array of subsequent diversification reactions.

Cp?Rh(III)-Catalyzed Mild Addition of C(sp3)-H Bonds to α,β-Unsaturated Aldehydes and Ketones

A Rh(III)-catalyzed addition of benzylic C(sp3)-H bond to α,β-unsaturated ketones/aldehydes has been realized, leading to efficient synthesis of γ-aryl ketones/aldehydes. This atom-economic reaction proceeded under mild and redox-neutral conditions with a broad substrate scope. Besides benzylic C-H, allylic C-H bonds are also applicable when assisted by O-methyl ketoxime directing groups.

Rh-Catalyzed Direct Amination of Unactivated C(sp3)?H bond with Anthranils Under Mild Conditions

C?N Bond formation is of great significance due to the ubiquity of nitrogen-containing compounds. Here, a mild and efficient RhIII-catalyzed C(sp3)?H aryl amination reaction is reported. Anthranil is employed as the nitrogen source with 100 % atom efficiency. This C?H amination reaction exhibits broad substrate scope without using any external oxidants. Mechanistic studies including rhodacycle intermediates, H–D exchange, kinetic isotope effect (KIE) experiments, and in situ IR are presented.