25105-58-2Relevant academic research and scientific papers
Exploiting the 4-Phenylquinazoline Scaffold for the Development of High Affinity Fluorescent Probes for the Translocator Protein (TSPO)
Milite, Ciro,Barresi, Elisabetta,Da Pozzo, Eleonora,Costa, Barbara,Viviano, Monica,Porta, Amalia,Messere, Anna,Sbardella, Gianluca,Da Settimo, Federico,Novellino, Ettore,Cosconati, Sandro,Castellano, Sabrina,Taliani, Sabrina,Martini, Claudia
, p. 7897 - 7909 (2017/10/06)
The quinazoline class was exploited to search for a new translocator protein (TSPO) fluorescent probe endowed with improved affinity and residence time (RT). Computational studies on an "in-house" collection of quinazoline derivatives, featuring highly st
Structure-activity relationship refinement and further assessment of 4-phenylquinazoline-2-carboxamide translocator protein ligands as antiproliferative agents in human glioblastoma tumors
Castellano, Sabrina,Taliani, Sabrina,Viviano, Monica,Milite, Ciro,Da Pozzo, Eleonora,Costa, Barbara,Barresi, Elisabetta,Bruno, Agostino,Cosconati, Sandro,Marinelli, Luciana,Greco, Giovanni,Novellino, Ettore,Sbardella, Gianluca,Da Settimo, Federico,Martini, Claudia
, p. 2413 - 2428 (2014/04/17)
Structure-activity relationships (SARs) within the 4-phenylquinazoline-2- carboxamide series of translocator protein (TSPO) ligands have been explored further by the synthesis and TSPO binding affinity evaluation of N-benzyl-N-ethyl/methyl derivatives var
Aromatic aldehyde-catalyzed gas-phase decarboxylation of amino acid anion via imine intermediate: An experimental and theoretical study
Xiang, Zhang
, p. 149 - 156 (2013/10/22)
It is generally appreciated that carbonyl compound can promote the decarboxylation of the amino acid. In this paper, we have performed the experimental and theoretical investigation into the gas-phase decarboxylation of the amino acid anion catalyzed by the aromatic aldehyde via the imine intermediate on the basis of the tandem mass spectrometry (MS/MS) technique and density functional theory (DFT) calculation. The results show that the aromatic aldehyde can achieve a remarkable catalytic effect. Moreover, the catalytic mechanism varies according to the type of amino acid: (i) The decarboxylation of α-amino acid anion is determined by the direct dissociation of the C-C bond adjacent to the carboxylate, for the resulting carbanion can be well stabilized by the conjugation between α-carbon, C=N bond and benzene ring. (ii) The decarboxylation of non-α-amino acid anion proceeds via a SN2-like transition state, in which the dissociation of the C-C bond adjacent to the carboxylate and attacking of the resulting carbanion to the C=N bond or benzene ring take place at the same time. Specifically, for β-alanine, the resulting carbanion preferentially attacks the benzene ring leading to the benzene anion, because attacking the C=N bond in the decarboxylation can produce the unstable three or four-membered ring anion. For the other non-α-amino acid anion, the C=N bond preferentially participates in the decarboxylation, which leads to the pediocratic nitrogen anion.
Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
Adam, Claudia G.,Fortunato, Graciela G.,Mancini, Pedro M.
scheme or table, p. 460 - 465 (2010/04/30)
This work presents a new approach using ionic liquids, namely ethylammonium nitrate. The aim was to analyze how the addition of small amounts of a protic ionic liquid to a pure molecular solvent, modifies the microscopic characteristics of a reaction medium. In order to achieve this, a kinetic study of nucleophilic aromatic substitution reactions between 1-fluoro-2, 4-dinitrobenzene and 1-butylamine or piperidine was developed in this type of binary mixtures. We have detected nucleophiles competition originated by the presence of the ionic solvent at very low concentrations, observing the ethylamine derivative as the main substitution product. Moreover, in the light of previous results we have confirmed that the protic ionic liquid can act as both Broensted acid and/or nucleophile. In this connection, we have selected the nucleophilic addition of amines to carbonyl compounds as reaction model. The protic ionic liquid in the presence of aromatic aldehydes substituted by electron-donating groups makes possible the formation of the corresponding imines with good yields. The results demonstrated that the influence of the protic ionic liquid is very important in the course of both reaction systems. Copyright
Synthesis of 2-alkyl-1-aryl-1,2-dihydrochromeno[2,3-c]pyrrole-3,9-dione derivatives
Vydzhak,Panchishin, S. Ya.
experimental part, p. 2391 - 2397 (2009/05/30)
A preparative procedure for the synthesis of 2-alkyl-1-aryl-1,2- dihydrochromeno[2,3-c]pyrrole-3,9-diones from methyl 4-(o-hydroxyphenyl)-2,4- dioxobutanoate, aromatic aldehyde, and aliphatic amine is described.
Quantitative solid-state reactions of amines with carbonyl compounds and isothiocyanates
Kaupp, Gerd,Schmeyers, Jens,Boy, Juergen
, p. 6899 - 6911 (2007/10/03)
A series of solid-state reactions is reported of gaseous or solid amines with aldehydes to give imines, with solid anhydrides to give diamides (therefrom imides) or amidic carboxylic salts or imides, with solid imides to give diamides, with solid lactones or carbonates to give functionalized carbamic esters, with polycarbonates to give degradative aminolysis, and with solid isothiocyanates to give thioureas. Diamides give imides by solid-state thermolysis or acid catalysis. Various double, two-step, 3-cascade, and sequential reactions are reported in the solid state without melting. The yields are quantitative in 53 reported reaction examples and no workup (except for washings in four cases) is required in the 100% yield reactions. Three initially solid-state reactions but with liquid product were not quantitative. An upscaling to the kg scale shows promise of the technique for large scale applications. Supermicroscopic analyses with AFM elucidate the solid-state mechanism by virtue of far-reaching anisotropic molecular movements in three-step processes. Gas-solid aminolyses of polycarbonates are also studied with AFM. The implications to sustainable chemistry are discussed. (C) 2000 Elsevier Science Ltd.
Reactions of N-Chloro-N-alkylbenzylamines with Amines in Acetonitrile. Origin of Steric Effect in Imine-Forming Elimination
Cho, Bong Rae,Suh, Young Wook
, p. 2855 - 2858 (2007/10/02)
Reaction of N-chloro-N-alkylbenzylamines in which the alkyl group is Me, Et, i-Pr, sec-Bu, and t-Bu with MeNH2 and Et2NH in MeCN have been studied kinetically.The eliminations are quantitative and regiospecific, producing only N-benzylidenealkylamines.The relative rates of elimination for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents are 1/0.6/0.4/0.3/0.1 with MeNH2 and 1/0.5/0.3/0.2/0.03 with Et2NH, respectively.Comparison with published data reveals that Charton's value for the imine-forming elimination decreases with the variation of the base-solvent from MeONa-MeOH to MeNH2-MeCN but increases when the base is changed from MeNH2 to Et2NH.For a given base, Hammett ρ and kH/kD values decrease and the ΔH(excit.) and ΔS(excit.) values increase with bulkier alkyl substituents.From these results, the origin of the steric effect in imine-forming elimination is attributed to the repulsive interaction between the alkyl group and the base in the transition state.
Reactions of N-Chlorobenzylalkylamines with Sodium Methoxide in Methanol. Steric Effects in Elimination Reactions
Cho, Bong Rae,Maeng, Jun Ho,Yoon, Jong Chan,Kim, Tae Rin
, p. 4752 - 4756 (2007/10/02)
Reactions of N-chlorobenzylalkylamines in which the alkyl group is Me, Et, i-Pr, t-Bu, and sec-Bu with MeONa-MeOH have been investigated kinetically.The eliminations are quantitative and regiospecific, producing only benzylidenealkylamines.The reactions are first order in base and first order in substrate, and an E2 mechanism is evident.The relative rates of elimination at 25 deg C are 1/0.5/0.3/0.2/0.01 for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents, respectively.The results are attributed to repulsive interaction between the alkyl group and the base in the transition state.Hammett ρ and kH/kD values decreased, but the ΔH(excit.) and ΔS(excit.) values increased with bulkier alkyl substituents.Changes in the transition-state parameters with the substrate steric effect are interpreted with variation in structure of the imine-forming transition states.
Is Oxygen Abstraction by Nucleophilic Reagents a Characteristic Reaction of Oxaziridines ?
Hata, Yoshiteru,Watanabe, Masamichi
, p. 610 - 614 (2007/10/02)
The reaction of oxaziridines with nucleophilic reagents was studied.The summarized results are as follows. (1) The nucleophilic reactions occur preferentially on the nitrogen atom and the oxaziridine decomposes into a carbonyl compound and an ylide. (2) The reaction site shifts from nitrogen toward oxygen as the bulk of the ring substituents increases. (3) Cis isomers show faster reaction than trans isomers. (4) The carbon atom of the oxaziridine ring is completely inert to nucleophilic reagents.
