Category: 19128-48-4

Tuccinardi, Tiziano; Bertini, Simone; Martinelli, Adriano; Minutolo, Filippo; Ortore, Gabriella; Placanica, Giorgio; Prota, Giovanni; Rapposelli, Simona; Carlson, Kathryn E.; Katzenellenbogen, John A.; Macchia, Marco published the artcile< Synthesis of Anthranylaldoxime Derivatives as Estrogen Receptor Ligands and Computational Prediction of Binding Modes>, Reference of 19128-48-4, the main research area is anthranyl aldoxime preparation estrogen receptor ligand.

N-Me-anthranylaldoximes possess a hydrogen-bonded pseudocyclic A’ ring in place of the typical phenolic A-ring that is characteristic of most estrogen receptor (ER) ligands. We have investigated the role played by substituents introduced into either one or both of the peripheral 3- and 4-Ph rings in modulating ER binding affinity. An efficient synthetic strategy was employed for the preparation of differentially substituted 3- and 4-aryl derivatives that involved exploiting the different reactivity of bromo- vs. chloro-aryl groups in palladium-catalyzed cross-couplings. The binding data showed that ERα affinity could be improved by a single p-OH group in the 4-Ph ring, whereas the same substitution on the 3-Ph ring caused a dramatic reduction of ERβ affinity. The most ERα-selective compound was the one with two p-OH groups on both Ph substituents. To rationalize these results, ligand docking followed by mol. mechanics Poisson-Boltzmann/surface area (MM-PBSA) studies were carried out. These analyses suggested a mol. basis for the interaction of these compounds with the ERs and enabled the development of models able to predict the mode of ligand binding.

Journal of Medicinal Chemistry published new progress about Estrogen receptor α Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 19128-48-4 belongs to class bromides-buliding-blocks, and the molecular formula is C6H3BrClNO2, Reference of 19128-48-4.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liedholm, Brita published the artcile< Copper(I)-induced bromine-hydrogen exchange of 2,3-dibromoanilines>, Application In Synthesis of 19128-48-4, the main research area is copper reduction dibromoaniline; aniline dibromo debromination copper; debromination dibromoaniline copper ion.

The Cu(I)-induced Br/H exchange reaction of 2,3-dibromoaniline and 5-substituted 2,3-dibromoanilines in the 2-position has been kinetically studied in aqueous HOAc-HCl medium at 90°. The dehalogenation reaction is 2nd order, 1st in both substrate and Cu+, and may be interpreted as a reductive substitution, composed of two 1-electron steps. The 2,3-dibromophenol was only qual. examined but gave similar results.

Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry published new progress about Debromination. 19128-48-4 belongs to class bromides-buliding-blocks, and the molecular formula is C6H3BrClNO2, Application In Synthesis of 19128-48-4.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Minutolo, Filippo; Antonello, Michela; Bertini, Simone; Rapposelli, Simona; Rossello, Armando; Sheng, Shubin; Carlson, Kathryn E.; Katzenellenbogen, John A.; Macchia, Marco published the artcile< Synthesis, binding affinity, and transcriptional activity of hydroxy- and methoxy-Substituted 3,4-Diarylsalicylaldoximes on estrogen receptors α and β>, Safety of 2-Bromo-1-chloro-3-nitrobenzene, the main research area is estrogen receptor affinity diarylsalicylaldoxime structure activity.

An effective, unprecedented replacement of the prototypical phenolic ‘A-ring’ of estrogens with an oxime and a hydroxy-moiety of the salicylaldoxime derivative 3,4-diphenyl-substituted (1a) opened the way to study structure-activity relationships of a new class of estrogen receptor (ER)-ligands. Herein, we present a study of the ER binding properties and transcriptional activities of analogs of 3,4-diphenylsalicylaldoxime (1a). The introduction of p-OH and p-OMe groups on the Ph substituents of 1a, as in compounds 1b-g, results in unique structure-activity profiles. The preparation of the hetero-disubstituted compounds (1b-e) was accomplished by a sequential introduction of different 3- and 4-aryl groups, obtained by exploiting the different reactivity of the bromine vs. chlorine substituents on the precursor, 2-bromo-3-chloronitrobenzene (5), in the palladium-catalyzed cross-coupling reactions. The results of the biol. tests show that the introduction of one hydroxy group on the 3-Ph substituent of the lead compound 1a improved the binding affinity on ERβ (1c), whereas the introduction of the same group on the 4-Ph substituent of 1a gave a compound (1e) with better affinity properties on ERα. The introduction of two hydroxyl groups in the para-position of both Ph substituents of 1a, as in 1g, lowered the binding on both receptor subtypes. In transcription assays, the ERα agonist character of this class of ligands is enhanced by the presence of a p-hydroxy or p-methoxy in the ‘distal’ Ph ring, whereas substitution on the other Ph ring does not substantially modify the partial agonist character of 1a. Thus, results from the binding and transcription assays illustrate that this class of ER ligands has a distinct structure-activity profile on the two ER subtypes, being potent nearly full agonists on ERα and weak, partial antagonists on ERβ.

Bioorganic & Medicinal Chemistry published new progress about Affinity. 19128-48-4 belongs to class bromides-buliding-blocks, and the molecular formula is C6H3BrClNO2, Safety of 2-Bromo-1-chloro-3-nitrobenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yadav, J. S.; Subba Reddy, B. V. published the artcile< Microwave-assisted efficient synthesis of N-arylamines in dry media>, Synthetic Route of 19128-48-4, the main research area is arylamine microwave assisted preparation; aryl halide reaction secondary amine microwave.

A novel and efficient synthesis of N-arylamines by the reaction of activated aryl halides with secondary amines in the presence of basic Al2O3 under microwave irradiation in solvent free conditions is reported.

Green Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 19128-48-4 belongs to class bromides-buliding-blocks, and the molecular formula is C6H3BrClNO2, Synthetic Route of 19128-48-4.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liedholm, Brita published the artcile< Copper(I) catalyzed replacement of bromine by chloride ion in halonitrobenzenes>, Safety of 2-Bromo-1-chloro-3-nitrobenzene, the main research area is halo nitro benzenes substitution; nitro halo benzenes substitution; substitution halo nitro benzenes; benzenes halo nitro substitution.

The Cu(I) catalysed exchange of Br for Cl in aqueous HCl-AcOH was kinetically studied under homogeneous conditions in 2-bromo-3-chloronitrobenzene, 2,3-dibromonitrobenzene, and other halonitrobenzenes at 80, 90, and 98°. The concentration of the catalyzing Cu(I) complex, CuCl2-, was estimated from the dependence of the first-order rate on Cl- concentration A strong accelerating effect of an o-nitro group was observed The possibility of a transition state in which the o-nitro group participates with CuCl2- and the Br to be replaced in the formation of a tetrahedral Cu(I) complex is discussed and the activation parameters are presented.

Acta Chemica Scandinavica (1947-1973) published new progress about Substitution reaction catalysts. 19128-48-4 belongs to class bromides-buliding-blocks, and the molecular formula is C6H3BrClNO2, Safety of 2-Bromo-1-chloro-3-nitrobenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary