76893-44-2

Basic information

• Product Name: 3-nitro-2-phenoxypyridine
• Synonyms: 3-nitro-2-phenoxypyridine
• CAS NO: 76893-44-2
• Molecular Formula: C₁₁H₈N₂O₃
• Molecular Weight: 216.19282
• Mol File: 76893-44-2.mol

Chemical Properties

• Melting Point: 94-94.5 °C(Solv: ethanol (64-17-5))
• Boiling Point: 329.9±27.0 °C(Predicted)
• Appearance: /
• Density: 1.309±0.06 g/cm3(Predicted)
• PKA: -1.49±0.22(Predicted)
• CAS DataBase Reference: 3-nitro-2-phenoxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-nitro-2-phenoxypyridine(76893-44-2)
• EPA Substance Registry System: 3-nitro-2-phenoxypyridine(76893-44-2)

Safety Data

• Hazardous Substances Data: 76893-44-2(Hazardous Substances Data)

Upstream product

• 5470-18-8 2-Chloro-3-nitropyridine 
• 100-67-4 potassium phenolate 
• 3229-70-7 phenolate 
• 108-95-2 phenol 
• 1480-87-1 2-fluoro-3-nitropyridine 
• 6332-56-5 3-nitropyridone 
• 694-53-1 phenylsilane 

Downstream Products

• 28664-62-2 3-amino-2-phenoxypyridine 
• 476453-77-7 N-(2-phenoxy-3-pyridinyl)methanesulfonimide 
• 180677-33-2 N-(2-phenoxypyridin-3-yl)hydroxylamine 
• 26820-73-5 3-nitro-2-(pyrrolidin-1-yl)pyridine 
• 26820-68-8 N-(3-nitropyridin-2-yl)butylamine 
• 26930-71-2 3-nitro-2-(piperidin-1-yl)pyridine 
• 1400637-82-2 C₂₁H₁₉BrN₂O₃ 
• 1400637-67-3 C₂₁H₁₉⁽¹⁸⁾FN₂O₃ 
• 1245623-84-0 N-[2-(2-fluoroethoxy)benzyl]-N-(2-phenoxy pyridin-3-yl)acetamide 
• 1207345-63-8 N-[2-(2-fluoroethoxy)-5-methoxybenzyl]-N-(2-phenoxypyridin-3-yl)acetamide 
• 253307-70-9 C₁₉H₁₈N₂O₂ 
• 1400637-54-8 C₂₁H₁₉FN₂O₃ 
• 1423008-63-2 C₁₈H₁₃F₂N₃O₂ 
• 1245623-79-3 C₂₂H₂₁⁽¹⁸⁾FN₂O₃ 

Relevant articles and documents

Chemical validation of a druggable site on Hsp27/HSPB1 using in silico solvent mapping and biophysical methods

Destabilizing mutations in small heat shock proteins (sHsps) are linked to multiple diseases; however, sHsps are conformationally dynamic, lack enzymatic function and have no endogenous chemical ligands. These factors render sHsps as classically “undruggable” targets and make it particularly challenging to identify molecules that might bind and stabilize them. To explore potential solutions, we designed a multi-pronged screening workflow involving a combination of computational and biophysical ligand-discovery platforms. Using the core domain of the sHsp family member Hsp27/HSPB1 (Hsp27c) as a target, we applied mixed solvent molecular dynamics (MixMD) to predict three possible binding sites, which we confirmed using NMR-based solvent mapping. Using this knowledge, we then used NMR spectroscopy to carry out a fragment-based drug discovery (FBDD) screen, ultimately identifying two fragments that bind to one of these sites. A medicinal chemistry effort improved the affinity of one fragment by ~50-fold (16 μM), while maintaining good ligand efficiency (~0.32 kcal/mol/non-hydrogen atom). Finally, we found that binding to this site partially restored the stability of disease-associated Hsp27 variants, in a redox-dependent manner. Together, these experiments suggest a new and unexpected binding site on Hsp27, which might be exploited to build chemical probes.

Method for preparing diarylether compound based on CO2 participated C-F bond activation

The invention discloses a method for preparing a diarylether compound based on CO2 participated C-F bond activation, which comprises the following steps: adding an acetonitrile solution of a 2-fluoropyridine compound into a reaction container, sequentially adding a catalyst palladium acetate Pd(OAc)2, alkali cesium carbonate and phenylsilane PhSiH3, and replacing with CO2 gas for three times, andreacting for 24 hours under the conditions that the CO2 pressure is 1atm and the temperature is 25 DEG C, adding an ice-water mixture after the reaction is finished, performing extraction reaction, dichloromethane extraction, organic phase merging and drying, reduced pressure distillation and silica gel column chromatography to obtain a target product, namely the white solid diarylether compound.Compared with the prior art, the method has the advantages of mild reaction temperature, good selectivity, high yield, easiness in industrialization and the like.

Substituent Effects of 2-Pyridones on Selective O-Arylation with Diaryliodonium Salts: Synthesis of 2-Aryloxypyridines under Transition-Metal-Free Conditions

An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y 1 lead compound analogue could be prepared in good yield over two steps.

Synthesis of pyrido[2,3-b][1,4]benzoxazepines via a Friedel-Crafts cyclization

(Formula Presented.) An efficient and practical method has been developed for the synthesis of 6-aryl-substituted pyrido[2,3-b][1,4]benzoxazepines via a Friedel-Crafts reaction of readily accessible 2-phenoxypyridin-3-amines and aromatic acids.

Discovery of dually acting small-molecule inhibitors of cancer-resistance relevant receptor tyrosine kinases EGFR and IGF-1R

Novel benzo-anellated furo- and pyrrolo[2,3-b]pyridines with a 4-benzylamine substitution have been evaluated as inhibitors of the epidermal growth factor receptor (EGFR). Substituent effects on the determined protein kinase affinity have been discussed based on varied benzylamine residues at the differently substituted molecular scaffolds. Docking studies were carried out in order to explore the potential binding modes of the novel inhibitors. The observed activity data encouraged the measurement of the inhibition of the insulin-like growth factor receptor (IGF-1R), which is known to play an important role in the cancer-resistance development against EGFR inhibitors via receptor heterodimerizations with IGF-1R. We identified novel dual inhibitors of both kinases and report their first cancer cell growth inhibition data.

For radioactive-derwed Pyridinil deriv. in vivo imaging

The present invention provides a novel radiolabeled aryloxyalinine derivative suitable for in vivo imaging. In comparison to known aryloxyalinine derivative in vivo imaging agents, the in vivo imaging agent of the present invention has better properties for in vivo imaging. The in vivo imaging agent of the present invention demonstrates good selective binding to the peripheral benzodiazepine receptor (PBR), in combination with good brain uptake and in vivo kinetics following administration to a subject.

Discovery of 2-(phenoxypyridine)-3-phenylureas as small molecule P2Y 1 antagonists

Two distinct G protein-coupled purinergic receptors, P2Y1 and P2Y12, mediate ADP-driven platelet activation. The clinical effectiveness of P2Y12 blockade is well established. Recent preclinical data suggest that P2Y1

Exploration of the structure-activity relationship of the diaryl anilide class of ligands for translocator protein - Potential novel positron emitting tomography imaging agents

A series of novel ligands based on the diaryl anilide (DAA) class of translocator protein (TSPO) ligands was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands and will be evaluated further as potential clinical imaging agents.

Discovery and selectivity-profiling of 4-benzylamino 1-aza-9-oxafluorene derivatives as lead structures for IGF-1R inhibitors

Recently the insuline-like growth factor receptor (IGF-1R) emerged as a promising target structure for the development of novel anti-cancer agents. IGF-1R plays a central role in both tumour progression and resistance development against anti-cancer drugs. We discovered 1-aza-9-oxafluorene derivatives as novel lead structures with submicromolar activities against IGF-1R. Structure-activity relationships (SARs) on a series of related receptor tyrosine kinases (RTKs) are discussed in the context of available crystal structures. A preliminary selectivity-profiling is demonstrated for the first compound series. Antiproliferative tumour cell line screening studies yielded one candidate as a promising cytostatic agent without significant toxic effects.

Nucleophilic heteroaromatic substitution: Kinetics of the reactions of nitropyridines with aliphatic amines in dipolar aprotic solvents

Rate data are reported for the reactions of 2-chloro-5-nitropyridine 2a, 2-chloro-3-nitropyridine 2b, and the corresponding 2-phenoxy derivatives 2c with n-butylamine, pyrrolidine and piperidine and 2d with n-butylamine and pyrrolidine in dimethyl sulfoxi