137352-78-4Relevant academic research and scientific papers
Selective Fatty Acid Amide Hydrolase Inhibitors as Potential Novel Antiepileptic Agents
Grillo, Alessandro,Fezza, Filomena,Chemi, Giulia,Colangeli, Roberto,Brogi, Simone,Fazio, Domenico,Federico, Stefano,Papa, Alessandro,Relitti, Nicola,Di Maio, Roberto,Giorgi, Gianluca,Lamponi, Stefania,Valoti, Massimo,Gorelli, Beatrice,Saponara, Simona,Benedusi, Mascia,Pecorelli, Alessandra,Minetti, Patrizia,Valacchi, Giuseppe,Butini, Stefania,Campiani, Giuseppe,Gemma, Sandra,Maccarrone, Mauro,Di Giovanni, Giuseppe
, p. 1716 - 1736 (2021)
Temporal lobe epilepsy is the most common form of epilepsy, and current antiepileptic drugs are ineffective in many patients. The endocannabinoid system has been associated with an on-demand protective response to seizures. Blocking endocannabinoid catabolism would elicit antiepileptic effects, devoid of psychotropic effects. We herein report the discovery of selective anandamide catabolic enzyme fatty acid amide hydrolase (FAAH) inhibitors with promising antiepileptic efficacy, starting from a further investigation of our prototypical inhibitor 2a. When tested in two rodent models of epilepsy, 2a reduced the severity of the pilocarpine-induced status epilepticus and the elongation of the hippocampal maximal dentate activation. Notably, 2a did not affect hippocampal dentate gyrus long-term synaptic plasticity. These data prompted our further endeavor aiming at discovering new antiepileptic agents, developing a new set of FAAH inhibitors (3a-m). Biological studies highlighted 3h and 3m as the best performing analogues to be further investigated. In cell-based studies, using a neuroblastoma cell line, 3h and 3m could reduce the oxinflammation state by decreasing DNA-binding activity of NF-kB p65, devoid of cytotoxic effect. Unwanted cardiac effects were excluded for 3h (Langendorff perfused rat heart). Finally, the new analogue 3h reduced the severity of the pilocarpine-induced status epilepticus as observed for 2a.
ZnAl2O4–Bi2O3 composite nano-powder as an efficient catalyst for the multi-component, one-pot, aqueous media preparation of novel 4H-chromene-3-carbonitriles
Ghashang, Majid
, p. 4191 - 4205 (2016)
Abstract: A composite structure of ZnAl2O4–Bi2O3 nanopowder was prepared from the reaction of a watery solution of Zn(NO3)2, Al(NO3)3, and Bi(NO3)3 with a dilute solution of amino ethanol in water via a simple precipitation-complexation method. The as-prepared composite was used for the one-pot synthesis of 2-amino-4-aryl-7-(pyrrolidin-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-7-(piperidin-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-7-(1H-pyrrol-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-6-(2-(piperidin-1-yl)ethyl)-4H-chromene-3-carbonitrile and 2-amino-4-aryl-6-(1H-pyrrol-1-yl)-4H-chromene-3-carbonitrile derivatives. This procedure is very simple and affords excellent yields. Graphical Abstract: [Figure not available: see fulltext.]
Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide
Bismuto, Alessandro,Boehm, Philip,Morandi, Bill,Roediger, Sven
supporting information, p. 17887 - 17896 (2020/08/19)
An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.
Nano sulfated titania as a heterogeneous solid acid catalyst for the synthesis of pyrroles by clauson-kaas condensation under solvent-free conditions
Hosseini-Sarvari,Najafvand-Derikvandi,Jarrahpour,Heiran
, p. 1732 - 1739 (2014/05/06)
A new and environmentally benign method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-dimethoxytetrahydrofuran with amines and diamines in the presence of nano sulfated titania under solvent-free conditions is presented. This new protocol features simple operation, easy availability, stability, and eco-friendliness of catalyst, as well as high to excellent yields of products. In addition, we report for the first time an alternative method for the synthesis of pyrroles from aromatic amines containing the β-lactam fragment using nano sulfated titania as catalyst.
L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
Wang, Ping,Ma, Fei-Ping,Zhang, Zhan-Hui
, p. 259 - 262 (2014/11/07)
l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.
A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water
Ma, Fei-Ping,Li, Pei-He,Li, Bao-Le,Mo, Li-Ping,Liu, Ning,Kang, Hui-Jun,Liu, Ya-Nan,Zhang, Zhan-Hui
, p. 34 - 41 (2013/06/26)
A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.
An improved catalyst system for the Pd-catalyzed fluorination of (hetero)aryl triflates
Lee, Hong Geun,Milner, Phillip J.,Buchwald, Stephen L.
supporting information, p. 5602 - 5605 (2013/11/19)
The stable Pd(0) species [(1,5-cyclooctadiene)(L·Pd)2] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.
Clauson-kaas-type synthesis of pyrrolyl-phenols, from the hydrochlorides of aminophenols, in the presence of nicotinamide
Chatzopoulou, Maria,Kotsampasakou, Eleni,Demopoulos, Vassilis J.
supporting information, p. 2949 - 2954 (2013/09/02)
A facile Clauson-Kaas-type pyrrolyl-phenol synthesis has been achieved in the presence of nicotinamide, which is inexpensive and nontoxic. The starting material is aminophenol hydrochloride. This is advantageous in certain cases because it is the only isolatable form of the corresponding aminophenol.
Rearrangements of Pyrrole and Indole Substituted Enol Esters of Cyclohexane-1,3-dione
Oliver, James E.,Lusby, William R.,Waters, Rolland M.
, p. 1565 - 1568 (2007/10/02)
Enol esters 3a and 3b, from cyclohexane-1,3-dione and pyrrole-2-carbonyl chloride and indole-2-carbonyl chloride, respectively, rearranged in the presence of triethylamine to the enamino acids 7 and 12.In the presence of cyanide, 3b, also underwent the expected rearrangement to 4b, whereas only 7 was formed from 3a.Treatment of 7 with mercuric acetate in hot acetic acid resulted in decarboxylation and aromatization to phenol 9.
