51626-47-2Relevant academic research and scientific papers
A Friedel-Crafts alkylation mechanism using an aminoindanol-derived thiourea catalyst
Roca-Lopez, David,Marques-Lopez, Eugenia,Alcaine, Ana,Merino, Pedro,Herrera, Raquel P.
, p. 4503 - 4510 (2014)
Computational calculations based on experimental results shed light on the mechanistic proposal for a Friedel-Crafts alkylation reaction between indole and nitroalkenes, catalysed by a chiral aminoindanol-derived thiourea. In our hypothesis both substrate
Gold(I)-Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis
Izaga, Anabel,Herrera, Raquel P.,Gimeno, M. Concepción
, p. 1313 - 1321 (2017)
Several group 11 metal complexes with chiral thiourea organocatalysts have been prepared and tested as organocatalysts. The promising results on the influence of metal-assisted thiourea organocatalysts in the asymmetric Friedel–Crafts alkylation of indole
Hydrogen Bonding Networks in Chiral Thiourea Organocatalysts: Evidence on the Importance of the Aminoindanol Moiety
Gimeno, M. Concepción,Herrera, Raquel P.
, p. 5091 - 5099 (2016)
The crystal structures of four chiral thioureas, which are normally used as organocatalysts, are reported by the first time. Each compound is assembled in the crystal in a different way according to their chiral moiety in the thiourea skeleton, being depe
Thiourea-functionalized MIL-101(Cr) metal-organic framework as a hydrogen-bond-donating heterogeneous organocatalyst for the Friedel-Crafts alkylation and Biginelli reactions
Mohammadian, Reza,Amini, Mostafa M.,Shaabani, Ahmad
, (2020)
In the present paper, a functionally diverse thiourea-grafted MOF was fabricated via postsynthetic modification process through complexation of MIL-101(Cr) with pyridine containing thiourea ligand. This new modified material overcomes a significant tenden
Higher enantioselectivities in thiourea-catalyzed Michael additions under solvent-free conditions
Hestericová, Martina,?ebesta, Radovan
, p. 901 - 905 (2014)
Enantioselective Michael additions catalyzed by hydrogen-bonding catalysts produce many important compounds. Solvent-free reaction conditions in a ball mill can provide an improved enantioselectivity over the reaction in solution, due to lack of disruptiv
Hydrogen-Bonding-Assisted Cationic Aqua Palladium(II) Complex Enables Highly Efficient Asymmetric Reactions in Water
Kitanosono, Taku,Hisada, Tomoya,Yamashita, Yasuhiro,Kobayashi, Shū
, p. 3407 - 3411 (2021)
Metal-bound water molecules have recently been recognized as a new facet of soft Lewis acid catalysis. Herein, a chiral palladium aqua complex was constructed that enables carbon–hydrogen bonds of indoles to be functionalized efficiently. We embraced a ch
Calix[6]arene-based Br?nsted acids for molecular recognition and catalysis
Cera, Gianpiero,Cester Bonati, Federica,Bazzoni, Margherita,Secchi, Andrea,Arduini, Arturo
, p. 1546 - 1554 (2021/03/01)
We report the synthesis of a versatile trifluoromethylsulfonamide calix[6]arene derivative with Br?nsted acid features which can influence both molecular recognition and catalytic application. Indeed, in low polarity media, the trifluoromethyl-containing
A Catalytic One-Pot Synthesis of Indolyl Cyclobutanones
Porcu, Stefania,Rodriguez, Carla Aira,Frongia, Angelo,Secci, Francesco
supporting information, p. 925 - 932 (2020/12/14)
A general strategy for the synthesis of indolyl cyclobutanones via a tandem Bronsted acid catalyzed 2-hydroxycyclobutanone activation-indole nucleophilic addition has been exploited. The procedure leads to a wide range of 2- and 3-functionalized indole derivatives in good to high yields with broad substrate scope.
2-[1-(Dimethylamino)ethyl]ferrocenylphosphinic acid as an organocatalyst of Michael and Friedel—Crafts reactions
Gilmanova, L. H.,Miluykov, V. A.,Shekurov, R. P.,Zagidullin, A. A.
, p. 1415 - 1417 (2021/08/10)
Racemic 2-[1-(dimethylamino)ethyl]ferrocenylphosphinic acid was tested as an organocatalyst in the Michael and Friedel—Crafts reactions. The use of this zwitterion provides 78% conversion in the Michael reaction between cyclohexanone and β-nitrostyrene, a
Design, synthesis, and pharmacological profiling of cannabinoid 1 receptor allosteric modulators: Preclinical efficacy of C2-group GAT211 congeners for reducing intraocular pressure
Garai, Sumanta,Schaffer, Peter C.,Laprairie, Robert B.,Janero, David R.,Pertwee, Roger G.,Straiker, Alex,Thakur, Ganesh A.
, (2021/10/12)
Allosteric modulators of cannabinoid 1 receptor (CB1R) show translational promise over orthosteric ligands due to their potential to elicit therapeutic benefit without cannabimimetic side effects. The prototypic 2-phenylindole CB1R allosteric modulator, GAT211 (1), demonstrates preclinical efficacy in various disease models. The limited systematic structure–activity relationship (SAR) data at the C2 position of the indole ring within GAT211 invites the opportunity for further modifications to improve GAT211′s pharmacological profile while serving to amplify and variegate this library of therapeutically attractive agents. These considerations prompted this focused SAR study in which we substituted the GAT211 C2-phenyl ring with heteroaromatic substituents. The synthesized GAT211 analogs were then evaluated in vitro as CB1R allosteric modulators in cAMP and β-arrestin2 assays with CP55,940 as the orthosteric ligand. Furan and thiophene rings (15c-f and 15m) were the best-tolerated substituents at the C2 position of GAT211 for engagement with human CB1R (hCB1R). The SAR around the novel ligands reported allowed direct experimental characterization of the interaction profile of that pharmacophore with its binding domain in functional, human CB1R, thus offering guidance for accessing subsequent-generation hCB1R allosteric modulators as potential therapeutics. The most potent analog, 15d, markedly promoted orthosteric ligand binding to hCB1R. Pharmacological profiling in the GTPγS and mouse vas deferens assays demonstrated that 15d behaves as a CB1R agonist-positive allosteric modulator (ago-PAM), as confirmed electrophysiologically in autoptic neurons. In vivo, 15d was efficacious as a topical agent that significantly reduced intraocular pressure (IOP) in the ocular normotensive murine model of glaucoma. Since elevated IOP is a decisive risk factor for glaucoma and attendant vision loss, our data support the proposition that the 2-phenylindole class of CB1R ago-PAMs has therapeutic potential for glaucoma and other diseases where potentiation of CB1R signaling may be therapeutic.
