37056-74-9Relevant articles and documents
Nitrone synthesis via pair electrochemical coupling of Nitro-Compounds with Benzyl Alcohol Derivatives
Salehzadeh, Hamid,Mashhadizadeh, Mohammad Hossein
, p. 9307 - 9312 (2019/07/08)
Here we report a paired electrochemical coupling of readily accessible nitro-compounds with benzyl alcohols to yield nitrone derivatives. In this work, electrochemical behavior of nitrobenzene and benzyl alcohol derivatives was studied by cyclic voltammetry and controlled potential coulommetry. Electrochemical reactions have been performed in aqueous/ethanol (or acetonitrile) solutions by employing common graphite electrodes and a simple controlled current protocol which can make this strategy more appealing than other conventional pathways.
One-pot synthesis of nitrones from nitro compounds by in situ trapping of arylhydroxylamines
Kazemi, Foad,Ramdar, Moosa,Tavana, Bahram,Davarpanah, Jamal
, p. 1101 - 1107 (2017/05/10)
Abstract: Highly efficient, convenient, simple procedure and a highly chemoselective method has been described for the conversion of nitroarenes to their corresponding nitrone derivatives by employing SnCl2·2H2O and Na2CO3 in the grinding apparatus in solvent-free conditions. Biaryl nitrones can be achieved via the condensation of an aldehyde with an unstable arylhydroxylamine which is prepared in situ through the reduction of the corresponding nitro aromatic compound. Interestingly, the slow and nonselective reduction of nitroarene to arylhydroxylamine step was directed with the condensation of in situ-prepared arylhydroxylamine with aromatic aldehyde (second step). Moreover, this protocol was successfully used for preparation of valuable dinitrones from dialdehyde and nitro aromatic compounds. For dinitrone preparation, dialdehyde compounds were first synthesized by the reaction of salicylaldehyde and glycol derivatives. Then, dialdehydes were reacted with reduced nitro compounds in optimal conditions that we used for synthesis of biaryl nitrones. Graphical Abstract: [Figure not available: see fulltext.].
Synthesis and evaluation of novel 4-[(3H,3aH,6aH)-3-phenyl)-4,6-dioxo-2- phenyldihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-yl]benzoic acid derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents
Anand, Preet,Singh, Baldev
, p. 521 - 530 (2012/03/09)
The present study was designed to synthesize and evaluate pyrrolo-isoxazole benzoic acid derivatives as potential acetylcholinesterase (AChE) inhibitors for the management of Alzheimer's disease. The synthesis of pyrrolo-isoxazole benzoic acid derivatives involved ring opening cyclization of p-aminobenzoic acid with maleic anhydride to yield maleanilic acid, which in turn afforded N-arylmaleimide via ring closed cyclization. Azomethine-N-oxides were obtained by condensation of N-arylhydroxylamine with differently substituted benzaldehydes followed by refluxing of N-arylmaleimide with differently substituted azomethine-N-oxides to pyrrolo-isoxazole benzoic acid derivatives as cis- and trans-stereoisomers. The synthesized compounds were evaluated in vitro for AChE inhibitory activity in rat brain homogenate with donepezil as standard AChE inhibitor. Thereafter, the most potent test compound was evaluated for in vitro butyrylcholinesterase inhibitory activity and in vivo memory evaluation in scopolamine (0.4 mg/kg)-induced amnesia in mice by employing Morris water maze test. All pyrrolo-isoxazole benzoic acid derivatives demonstrated potent AChE inhibitory activity. Most of compounds exhibited similar activity to donepezil and four of them (7h, 7i, 8i, and 8h, IC50 = 19.1 ± 1.9-17.5 ± 1.5 nM) displayed higher inhibitory activity as compared to donepezil (21.5 ± 3.2 nM) with compound 8ia (IC50 = 17.5 ± 1.5 nM) being the most active one. The test compound 8ia also ameliorated scopolamine-induced amnesia in mice in terms of restoration of time spent in target quadrant (TSTQ) and escape latency time (ELT). It may be concluded that pyrrolo-isoxazole benzoic acid derivatives may be employed as potential AChE inhibitors.
