121501-63-1

Upstream product

• 108-45-2 m-phenylenediamine 
• 93-05-0 N,N-diethylaniline 
• 2198-58-5 N,N-diethyl-1,4-phenylenediamine dihydrochloride 
• 541-69-5 m-phenylenediamine dihydrochloride 
• 148-90-3 4-diethylamino-benzenediazonium; chloride 

Relevant academic research and scientific papers

Reactivity-based detection of copper(II) ion in water: Oxidative cyclization of azoaromatics as fluorescence turn-on signaling mechanism

An oxidative cyclization reaction transforms nonemissive azoanilines into highly fluorescent benzotriazoles. We have found that introduction of multiple electron-donating amino groups onto a simple o-(phenylazo)aniline platform dramatically accelerates its conversion to the emissive polycyclic product. Notably, this chemistry can be effected by μM-level concentrations of copper(II) ion in water (pH = 6-8) at room temperature to elicit >80-fold enhancement in the green emission at λem = 530 nm. Comparative kinetic and electrochemical studies on a series of structural analogues have established that the accelerated reaction rates correlate directly with a systematic cathodic shift in the oxidation onset potential of the azo precursors. In addition, single-crystal X-ray crystallographic analysis on the most reactive derivative revealed the presence of a five-membered ring intramolecular hydrogen-bonding network. An enhanced contribution of the quinoid-type resonance in such conformation apparently facilitates the mechanistically required proton transfer step, which, in conjunction with electron transfer at lower oxidation potential, contributes to a rapid cyclization reaction triggered by copper(II) ion in water.

Discovery and SAR of 2-arylbenzotriazoles and 2-arylindazoles as potential treatments for Duchenne muscular dystrophy

Families of 2-arylbenzotriazoles and 2-arylindazoles that show positive effects in screens predictive of endogenous utrophin upregulation have been identified. Synthesis and structure-activity relationships are described leading to compounds with attractive in vitro profiles.

TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY

There are disclosed compound of Formula (I) or (II) wherein A1, A2, A3, A4and A5, which may be the same or different, represent N or CR1, R9 represents - L -R3, in whi

APPLICATION OF FLUORESCENT TRIAZOLES TO ANALYTICAL CHEMISTRY. IV. DEVELOPMENT OF A NEW FLUORESCENT PROBE FOR BASIC DRUG-α1-ACID GLYCOPROTEIN BINDING MEASUREMENT

A fluorescent probe applicable to protein binding measurement was developed.Several 2-phenylbenzotriazolyl-5-amine derivatives having an amino group on the 2-phenyl ring were synthesized.Their fluorescence characteristics and the binding affinity to α1-acid glycoprotein (α1-AGP) were investigated.They were practically non-fluorescent in aqueous solution, but were highly fluorescent in the presence of α1-AGP.This fluorescence was due to the binding of these compounds to α1-AGP.Of all the compounds synthesized, 7-chloro-2-(p-diethylaminophenyl)-2H-benzotriazolyl-5-amine (CDBA) bound to α1-AGP most strongly and was used as a fluorescent probe.The binding parameters of CDBA were estimated by the fluormetric titration method to be log K = 6.18 and n = 0.40.The fluorescence of CDBA in the α1-AGP solution was markedly quenched in the presence of basic drugs, indicating that these drugs competitively displace CDBA bound to α1-AGP.The binding constants of the basic drugs were calculated, based on the decrease of fluorescence intensity in the presence of the drug.The binding strength of the drugs tested ranged from 4.7 to 6.8 as log K value.Keywords: fluorescent probe; fluorescence characteristics; protein binding; binding parameter; α-acid glycoprotein; competition; basic drug; benzotriazole: 7-chloro-2-(p-diethylaminophenyl)-2H-benzotriazolyl-5-amine