124643-63-6

Usage

Aromatic heterocyclic compound

Indole derivative
2-(3-FLUOROPHENYL)-1H-INDOLE is derived from indole, which is an aromatic heterocyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring.

Fluorine substituent

3-position of the phenyl ring
A fluorine atom is attached to the 3-position of the phenyl ring in the compound, which can influence its chemical reactivity, stability, and lipophilicity.

Use as an intermediate

Synthesis of pharmaceuticals and organic compounds
2-(3-FLUOROPHENYL)-1H-INDOLE is commonly used as a starting material or intermediate in the synthesis of various pharmaceuticals and organic compounds, facilitating the creation of more complex molecules.

Application in medicinal chemistry research

Development of new drugs
Its structure and properties make 2-(3-FLUOROPHENYL)-1H-INDOLE suitable for use in medicinal chemistry research, particularly in the development of new drugs targeting specific biological pathways.

Potential biological activity

Drug discovery
The indole core present in 2-(3-FLUOROPHENYL)-1H-INDOLE gives it potential biological activity, making it an interesting molecule for further exploration in the field of drug discovery.

Upstream product

• 124643-49-8 2-((3-fluorophenyl)ethynyl)aniline 
• 615-43-0 2-iodophenylamine 
• 1054567-09-7 C₁₄H₁₀FN₃ 
• 120-72-9 indole 
• 768-35-4 3-fluorophenylboronic acid 
• 610-66-2 2-nitro-benzeneacetonitrile 
• 455-36-7 1-(3-fluorophenyl)ethanone 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 2973-50-4 2-aminophenylacetonitrile 
• 62-53-3 aniline 
• 53631-18-8 2-bromo-1-(3-fluorophenyl)ethanone 
• 95-52-3 2-Fluorotoluene 
• 403-54-3 m-Fluorobenzonitrile 
• 609-73-4 o-nitroiodobenzene 

Downstream Products

• 1262302-61-3 2,2'-bis(3-fluorophenyl)-1H,1'H-3,3'-biindole 
• 1363261-66-8 (S)-N(α)-acetyl-2-(3-fluorophenyl)tryptophan methyl ester 
• 1416576-39-0 C₂₃H₂₀FNO₃S 
• 1416576-40-3 C₂₄H₂₀FNO₄ 
• 138867-17-1 2-(meta-fluoro)phenylquinazolin-4(3H)-one 

Relevant academic research and scientific papers

Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors

The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.

Application of Fluorine- And Nitrogen-Walk Approaches: Defining the Structural and Functional Diversity of 2-Phenylindole Class of Cannabinoid 1 Receptor Positive Allosteric Modulators

Cannabinoid 1 receptor (CB1R) allosteric ligands hold a far-reaching therapeutic promise. We report the application of fluoro- and nitrogen-walk approaches to enhance the drug-like properties of GAT211, a prototype CB1R allosteric agonist-positive allosteric modulator (ago-PAM). Several analogs exhibited improved functional potency (cAMP, β-arrestin 2), metabolic stability, and aqueous solubility. Two key analogs, GAT591 (6r) and GAT593 (6s), exhibited augmented allosteric-agonist and PAM activities in neuronal cultures, improved metabolic stability, and enhanced orthosteric agonist binding (CP55,940). Both analogs also exhibited good analgesic potency in the CFA inflammatory-pain model with longer duration of action over GAT211 while being devoid of adverse cannabimimetic effects. Another analog, GAT592 (9j), exhibited moderate ago-PAM potency and improved aqueous solubility with therapeutic reduction of intraocular pressure in murine glaucoma models. The SAR findings and the enhanced allosteric activity in this class of allosteric modulators were accounted for in our recently developed computational model for CB1R allosteric activation and positive allosteric modulation.

Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.

Pd-catalyzed C–H bond activation of Indoles for Suzuki reaction

Abstract: We present a practical method for Suzuki coupling by which unprotected or N-protected indoles may be selectively arylated in the C2-position through direct C–H bond activation by electrophilic Pd(TFA) 2 catalyst. The protocol is operationally simple as it is carried out in dioxane/water mixture, and air as the sole oxidant at room temperature. Various 2-arylated indoles were obtained in good yields. The protocol works for benzofuran, pyrrole and thiophene also. Graphic abstract: Selective C-2 arylation of heterocycles using Pd(II) catalyst via C–H activation was performed under ambient condition. C3–C2 migration of organopalladium intermediate controls the reaction pathway.[Figure not available: see fulltext.].

Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines

A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.

Synthetic method of 2-substituted indoles compounds

The invention discloses a synthetic method of 2-substituted indoles compounds, and belongs to the organic synthesis field. 2-fluorotoluene compound shown in formula 1 and nitrile compound shown in formula 2 mix with an organic solvent in the presence of strong alkali and cesium salt additives, and react to synthesize the 2-substituted indoles compounds shown in formula 3. The synthesis method of 2-substituted indoles compounds is simple, economical and has wider applicability, is suitable for large-scale production, and has a very important influence on the synthesis of indoles compounds.

Synthesis of Indoles through Domino Reactions of 2-Fluorotoluenes and Nitriles

Indoles are essential heterocycles in medicinal chemistry, and therefore, novel and efficient approaches to their synthesis are in high demand. Among indoles, 2-aryl indoles have been described as privileged scaffolds. Advanced herein is a straightforward, practical, and transition-metal-free assembly of 2-aryl indoles. Simply combining readily available 2-fluorotoluenes, nitriles, LiN(SiMe3)2, and CsF enables the generation of a diverse array of indoles (38 examples, 48–92 % yield). A range of substituents can be introduced into each position of the indole backbone (C4 to C7, and aryl groups at C2), providing handles for further elaboration.

Gold(i)-catalyzed synthesis of 2-substituted indoles from 2-alkynylnitroarenes with diboron as reductant

An efficient method for the synthesis of 2-substituted indoles via a diboron/base promoted tandem reductive cyclization of o-alkynylnitroarene under Au catalysis conditions has been disclosed. This reaction is efficient and convenient, affording 2-substituted indoles with broad functional groups tolerance and excellent yields.

Palladium-catalyzed tandem addition/cyclization in aqueous medium: Synthesis of 2-arylindoles

An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.

Palladium-catalyzed direct C2-arylation of free (N–H) indoles via norbornene-mediated regioselective C–H activation

A palladium-catalyzed direct C2-arylation reaction of free (N–H) indoles has been developed. This reaction relies on a norbornene-mediated C–H activation process on the indole ring, which features high regioselectivity and excellent functional group tolerance.