4560-41-2

Usage

InChI:InChI=1/C13H11NO3/c15-14(16)12-8-4-5-9-13(12)17-10-11-6-2-1-3-7-11/h1-9H,10H2

Upstream product

• 1024-41-5 benzyl tosylate 
• 824-39-5 sodium o-nitrophenate 
• 824-38-4 potassium 2-nitrophenoxide 
• 100-44-7 benzyl chloride 
• 88-75-5 2-hydroxynitrobenzene 
• 86255-27-8 silver(I) 2-nitrophenoxide 
• 620-05-3 iodomethylbenzene 
• 946-80-5 (benzyloxy)benzene 
• 100-39-0 benzyl bromide 
• 56135-94-5 Potassium benzylcarbonate 
• 1493-27-2 ortho-nitrofluorobenzene 
• 16554-53-3 2-Nitrophenolate ion 
• 100-51-6 benzyl alcohol 
• 91-23-6 2-Nitroanisole 

Downstream Products

• 20012-63-9 o-(benzyloxy)aniline 
• 4279-47-4 (2,4-dinitro-phenyl)-(4-nitro-benzyl)-ether 
• 861319-93-9 (2,4-dinitro-phenyl)-(2-nitro-benzyl)-ether 
• 109691-36-3 (2-benzyloxy-phenyl)-phenyl-diazene 
• 20289-27-4 7-benzyloxyindole 
• 833-50-1 2-phenylbenzo[d]oxazole 
• 88-75-5 2-hydroxynitrobenzene 
• 37021-63-9 2-nitro-4-benzylphenol 
• 3743-70-2 N-(2-hydroxyphenyl)benzamide 
• 1523-12-2 2-nitrophenyl benzoate 
• 100-44-7 benzyl chloride 
• 92200-02-7 1-(β-phenylethyloxy)-4-nitrobenzene 
• 34288-04-5 N-(o-benzyloxyphenyl) hydroxyl amine 
• 114984-49-5 N-(2-benzyloxy-phenyl)-N'-phenyl-hydrazine 

Relevant academic research and scientific papers

Structure-Based Optimization of 3-Phenyl-N-(2-(3-phenylureido)ethyl)thiophene-2-sulfonamide Derivatives as Selective Mcl-1 Inhibitors

Selective Mcl-1 inhibitors may overcome the drug resistance caused by current anti-apoptotic Bcl-2 protein inhibitors in tumors with Mcl-1 overexpression. Based on previously discovered compounds with a 3-phenylthiophene-2-sulfonamide core moiety, in this work, we have obtained new compounds with improved binding affinity and/or selectivity under the guidance of structure-based design. The most potent compounds achieved sub-micromolar binding affinities to Mcl-1 (Ki～ 0.4 μM) and good cytotoxicity (IC5015N-heteronuclear single-quantum coherence NMR spectra suggested that these compounds bound to the BH3-binding groove on Mcl-1. Several cellular assays revealed that FWJ-D4 as well as its precursor FWJ-D5 effectively induced caspase-dependent apoptosis, and their target engagement at Mcl-1 was confirmed by co-immunoprecipitation experiments. Treatment with FWJ-D5 at 50 mg/kg every 2 days on an RS4;11 xenograft mouse model for 22 days led to 75% reduction in tumor volume without body weight loss.

Efficient synthesis and antibacterial activity of N-(o-benzyloxy/hydroxyphenyl) benzohydroxamic acids

A modified one-pot two-step method has been developed to synthesize N-(o-benzyloxyphenyl) benzohydroxamic acids from o-benzyloxy nitrobenzene in good to excellent yields. The synthesized N-(o-benzyloxyphenyl) benzohydroxamic acids were subjected to benzyl

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

Ambident Reactivity of Phenolate Anions Revisited: A Quantitative Approach to Phenolate Reactivities

Prompted by the observation that the regioselectivities of phenolate reactions (C versus O attack) are opposite to the predictions by the principle of hard and soft acids and bases, we performed a comprehensive experimental and computational investigation of phenolate reactivities. Rate and equilibrium constants for the reactions of various phenolate ions with benzhydrylium ions (Aryl2CH+) and structurally related quinone methides have been determined photometrically in polar aprotic solvents. Quantum chemical calculations at the SMD(MeCN)/M06-2X/6-31+G(d,p) level confirmed that O attack is generally favored under kinetically controlled conditions, whereas C attack is favored under thermodynamically controlled conditions. Exceptions are diffusion-limited reactions with strong electrophiles, which give mixtures of products arising from O and C attack, as well as reactions with metal alkoxides in nonpolar solvents, where oxygen attack is blocked by strong ion pairing. The Lewis basicity (LB) and nucleophilicity (N, sN) parameters of phenolates determined in this work can be used to predict whether their reactions with electrophiles are kinetically or thermodynamically controlled and whether the rates are activation- or diffusion-limited. Comparison of the measured rate constants for the reactions of phenolates with carbocations with the Gibbs energies for single-electron transfer manifests that these reactions proceed via polar mechanisms.

First Total Synthesis of the Cytotoxic Carbazole Alkaloid Excavatine-A and Regioselective Annulation to Pyrano[2,3-a]carbazoles and [1,4]Oxazepino[2,3,4-jk]carbazoles

We describe the first total synthesis of the cytotoxic carbazole alkaloid excavatine-A. The carbazole framework was constructed through double C–H bond activation of a diarylamine by using our palladium(II)-catalyzed oxidative cyclization. Treatment of th

Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis

Given the huge dependence on dipolar, aprotic solvents such as DMF, DMSO, DMAc, and NMP in nucleophilic aromatic substitution reactions (SNAr), a simple and environmentally friendly alternative is reported. Use of a "benign-by-design" nonionic surfactant, TPGS-750-M, in water enables nitrogen, oxygen, and sulfur nucleophiles to participate in SNAr reactions. Aromatic and heteroaromatic substrates readily participate in this micellar catalysis, which takes place at or near ambient temperatures.

Synthesis of perspicamide A and related diverse analogues: Their bioevaluation as potent antileishmanial agents

The first protocol for the synthesis of perspicamide A and related diverse analogues has been developed from economical and readily available starting materials. Furthermore, a few synthesized analogues, 24a, 24b, 24c, 24d, and 24l, exhibited potent activ

Patterned recognition of amines and ammonium ions by a stimuli-responsive foldamer-based hexameric oligophenol host

A stimuli-responsive hexameric oligophenol host undergoes amine-induced co-operative folding from a more fluorescent, more linear structure into less fluorescent, more curved or helically folded states, enabling easy identification and classification of the bound amine guests. The Royal Society of Chemistry 2013.

Ipso-nitration of arylboronic acids with bismuth nitrate and perdisulfate

An efficient and one pot synthetic method of ipso-nitration of arylboronic acids has been developed. The high efficiency, general applicability, and broader substrate scope including heterocycles and functional groups make this method advantageous. Due to its simplicity, we expect to find application of this method in synthesis.

Synthesis of substituted 6H-benzo[c]chromenes: A palladium promoted ring closure of diazonium tetrafluoroborates

A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium sal