51626-47-2

Usage

InChI:InChI=1/C16H14N2O2/c19-18(20)11-15(12-6-2-1-3-7-12)14-10-17-16-9-5-4-8-13(14)16/h1-10,15,17H,11H2

Upstream product

• 120-72-9 indole 
• 102-96-5 (2-nitroethenyl)benzene 
• 95-20-5 2-methyl-1H-indole 
• 5153-67-3 nitrostyrene 
• 104-88-1 4-chlorobenzaldehyde 
• 100-42-5 styrene 
• 100-52-7 benzaldehyde 

Downstream Products

• 5027-78-1 2-phenyl-2-(3-indolyl)-1-aminoethane 

Relevant academic research and scientific papers

A Friedel-Crafts alkylation mechanism using an aminoindanol-derived thiourea catalyst

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

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

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

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

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

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

Design, synthesis, and pharmacological profiling of cannabinoid 1 receptor allosteric modulators: Preclinical efficacy of C2-group GAT211 congeners for reducing intraocular pressure

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.

Enantioselective Friedel-Crafts alkylation of indole with nitroalkenes in the presence of bifunctional squaramide organocatalysts

A series of chiral bifunctional quinine and 2-aminoDMAP based squaramide organocatalysts are evaluated in Friedel-Crafts alkylation of indoles with nitroolefins. These 3-substituted indole derivatives are synthesized in the presence of sterically encumber

A robust heterogeneous Co-MOF catalyst in azide-alkyne cycloaddition and Friedel-Crafts reactions as well as hydrosilylation of alkynes

Organic reactions using metal-organic frameworks (MOFs) as catalysts are promising with regard to their environmentally friendly features and potential catalyst recyclability. A robust Co(ii)-MOF {[Co2(l-mac)(4,4-bpt)(H2O)]·3.5H2O}n (1) and its enantiomer {[Co2(d-mac)(4,4-bpt)(H2O)]·3.5H2O}n (2) (l/d-mac = basic forms of l/d-malic acid, 4,4-Hbpt = 3,5-di(pyridin-4-yl)-4H-1,2,4-triazole) have been gram-scale prepared under solvothermal conditions. Structural analysis reveals that mac manages Co(ii) ions to form 1-D chains, which are further extended via 4,4-bpt connectors into a noninterpenetrating 3D framework architecture. It was found that 1 can be as a heterogeneous catalyst for multiple organic reactions, such as azide-alkyne cycloaddition and Friedel-Crafts reactions with good isolated yields and good recycle runs (at least five times without substantial degradation). Additionally, 1 can promote hydrosilylation of alkynes under harsh conditions with moderate yield. This journal is

Organo-Polyoxometalate-Based Hydrogen-Bond Catalysis

Several urea-inserted organo-polyoxometalates (POMs) derived from polyoxotungstovanadate [P2V3W15O61]9? were prepared. The insertion of the carbonyl into the polyoxometallic framework activates the ur