794-65-0

Usage

InChI:InChI=1/C13H8N2O6/c16-8-9-1-4-11(5-2-9)21-13-6-3-10(14(17)18)7-12(13)15(19)20/h1-8H

Upstream product

• 70-34-8 2,4-Dinitrofluorobenzene 
• 123-08-0 4-hydroxy-benzaldehyde 
• 97-00-7 1-chloro-2,4-dinitro-benzene 

Downstream Products

• 860724-83-0 4-(2,4-dinitro-phenoxy)-3-nitro-benzaldehyde 
• 4096-88-2 1-azido-2,4-dinitrobenzene 
• 839-93-0 1-(2,4-dinitrophenyl)piperidine 
• 51-28-5 2,4-Dinitrophenol 

Relevant academic research and scientific papers

A novel near-infrared xanthene-based fluorescent probe for detection of thiophenol: In vitro and in vivo

Thiophenol (or PhSH) is widely utilized for producing pesticides, dyes, and pharmaceuticals. However, high-concentration thiophenol not only has adverse effects on living organisms, but also causes environment pollution. Herein, we designed and synthesize

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.

Xanthene derivative and preparing method and application thereof

The invention relates to the technical field of fluorescent probes, in particular to a xanthene derivative and a preparing method and application thereof. The derivative can be used as a fluorescent probe to realize rapid, sensitive and specific detection

Kinetic study on SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes with Azide ion: Effect of changing nucleophile from hydroxide to Azide ion on reaction mechanism and reactivity

Second-order rate constants (kN3-) for SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes (2a-2h) with (Formula presented.) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C have been measured spectrophotometrically. The Bronsted-type plot is linear with β1g=-0.38. The Hammett plots correlated with (Formula presented.) constants exhibit highly scattered points. In contrast, the Yukawa-Tsuno plot results in an excellent linear correlation with ρY = 1.02 and r = 0.51, indicating that a negative charge develops partially on the O atom of the leaving Y-substituted-phenoxy moiety in the transition state. Accordingly, the reactions have been concluded to proceed through a stepwise mechanism, in which expulsion of the leaving group occurs in the rate-determining step. Comparison of kN3- with the kOH- values reported previously for the corresponding reactions with OH has revealed that (Formula presented.) is only 6- to 26-fold than OH toward substrates 2a-2h, although the former is over 11 pKa units less basic than the latter. Solvation and polarizability effects have been suggested to be responsible for the unusual reactivity shown by (Formula presented.) and OH. Effects of changing nucleophile from OH to (Formula presented) on reaction mechanism and reactivity are discussed in detail.

Kinetic study on SNAr reaction of 1-Y-substituted-phenoxy-2,4- dinitrobenzenes with hydroxide ION: Effect of substituent y on reactivity and reaction mechanism

A kinetic study is reported for the SNAr reaction of 1-Y-substituted- phenoxy-2,4-dinitrobenzenes (1a-1h) with OH- in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The second-order rate constant (kOH-) increases as the substituent Y in the leaving group changes from an electron-donating group (EDG) to an electronwithdrawing group (EWG). The Bronsted-type plot for the reactions of 1a-1h is linear with βlg = -0.16, indicating that the reactivity of substrates 1a-1h is little affected by the leaving-group basicity. A linear Bronsted-type plot with βlg = -0.3 ± 0.1 is typical for reactions reported previously to proceed through a stepwise mechanism in which formation of a Meisenheimer complex is the rate-determining step (RDS). The Hammett plot correlated with σY o constants results in a much better correlation than that correlated with σY - constants, implyng that no negative charge is developing on the O atom of the leaving group (or expulsion of the leaving group is not advanced at all in the TS). This excludes a possibility that the SNAr reaction of 1a-1h with OH- proceeds through a concerted mechanism or via a stepwise pathway with expulsion of the leaving group being the RDS. Thus, the current reactions have been concluded to proceed through a stepwise mechanism in which expulsion of the leaving group occurs rapidly after the RDS.

Kinetic study on SNAr reaction of 1-(Y-Substituted-phenoxy)-2,4- dinitrobenzenes with cyclic secondary amines in acetonitrile: Evidence for cyclic transition-state structure

A kinetic study is reported for SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes (1a-1h) with amines in MeCN. The plots of pseudo-first-order rate constant versus amine concentration curve upward, indicating that the reactions are catalyzed by a second amine molecule. The Br?nsted-type plots for the reaction of 1-(4-nitrophenyl)-2,4- dinitrobenzene (1a) with secondary amines are linear with βnuc = 1.10 and 0.85 for the uncatalyzed and catalyzed reactions, respectively, while the Yukawa-Tsuno plots for the reactions of 1a-1h with piperidine result in excellent linear correlations with ρY = 1.85 and r = 0.27 for the uncatalyzed reaction and ρY = 0.73 and r = 0.23 for the catalyzed reaction. The catalytic effect decreases with increasing amine basicity or electron-withdrawing ability of the substituent Y in the leaving group. Activation parameters calculated from the rate constants measured at five different temperatures for the catalyzed reaction of 1a with piperidine are ΔH? = 0.38 kcal/mol and ΔS? = -55.4 cal/(mol K). The catalyzed reaction from a Meisenheimer complex (MC ±) is proposed to proceed through a concerted mechanism with a cyclic transition-state rather than via a stepwise pathway with an anionic intermediate, MC-. Deuterium kinetic isotope effects provide further insight into the nature of the concerted transition state.