21182-07-0

Basic information

• Product Name: 2-PYRIDIN-4-YL-1H-INDOLE
• Synonyms: 2-PYRIDIN-4-YL-1H-INDOLE;2-(4-PYRIDINYL)-1H-INDOLE;4-(1H-Indol-2-yl)pyridine;1H-INDOLE,2-(4-PYRIDINYL)-
• CAS NO: 21182-07-0
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.23
• Mol File: 21182-07-0.mol

Chemical Properties

• Boiling Point: 405.1°Cat760mmHg
• Flash Point: 184.4°C
• Appearance: /
• Density: 1.211g/cm³
• Vapor Pressure: 2.1E-06mmHg at 25°C
• Refractive Index: 1.688
• Sensitive: Light Sensitive
• CAS DataBase Reference: 2-PYRIDIN-4-YL-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PYRIDIN-4-YL-1H-INDOLE(21182-07-0)
• EPA Substance Registry System: 2-PYRIDIN-4-YL-1H-INDOLE(21182-07-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 21182-07-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H10N2/c1-2-4-12-11(3-1)9-13(15-12)10-5-7-14-8-6-10/h1-9,15H

Upstream product

• 1122-54-9 methyl (4-pyridyl) ketone 
• 100-63-0 phenylhydrazine 
• 100-48-1 pyridine-4-carbonitrile 
• 95-52-3 2-Fluorotoluene 
• 95-51-2 o-chloroaniline 
• 615-43-0 2-iodophenylamine 
• 29944-58-9 4-(Indolyl-⁽²⁾)-1-methyl-pyridiniumiodid 
• 39585-84-7 (E)-2-phenyl-1-(1-(pyridin-4-yl)ethylidene)hydrazine 

Downstream Products

• 590390-88-8 2-(4-pyridyl)indole-3-carboxaldehyde 
• 1416576-50-5 C₂₃H₂₀N₂O₄ 
• 1337932-62-3 2-(pyridin-4-yl)-3-[(3',4',5'-trimethoxyphenyl)thio]-1H-indole 
• 21199-47-3 4-indol-2-yl-1-(3-trimethylammonio-propyl)-pyridinium; dibromide 

Relevant articles and documents

Syntheses of 2-substituted indoles and fused indoles by photostimulated reactions of o-iodoanilines with carbanions by the SRN1 mechanism

2-Substituted indoles (5a,b and 7) and fused indoles (9a-c, 11a,b, and 12) have been obtained by the SRN1 mechanism from photostimulated reactions of o-iodoaniline (1) and 1-halo-2-naphthalen-2-ylamines (3a,b) with enolate ions of acyclic (acet

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

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.

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.

Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors

New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized 5. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCI/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.

INDOLIC DERIVATIVES AND USE THEREOF IN MEDICAL FIELD

The present invention concerns indolic derivatives and use thereof in medical field. Particularly, the invention concerns 3-[(3',4',5'- trimethoxyphenyl)thio]-1 H-indole derivatives and bioisosteric derivatives thereof and their use for the treatment of tumours.

Well-defined NHC-Pd complex-mediated intermolecular direct annulations for synthesis of functionalized indoles (NHC = N-hetero-cyclic carbene)

As alternatives to the common tertiary phosphine/Pd systems, well-defined N-heterocyclic carbene-Pd complexes have been proven to be highly efficient precatalysts for intermolecular direct annalution of o-haloanilines and ketones at lower catalyst loadings. A highly efficient and practical protocol for synthesis of functionalized indoles was developed using (IPr)Pd(acac)Cl as catalyst. Both o-bromoanilines and o-chloroanilines gave rise to efficient coupling under the reaction conditions. Related to acyclic ones, cyclic ketones coupled more effectively with o-haloanilines. With [Pd(IPr)2] as catalyst, the base-sensitive groups including OH and CO2H groups could be tolerated. Copyright

2-Indolyl Imidazo [4,5-d] Phenanthroline Derivatives and Their Use in the Treatment for Cancer

2-indolyl imidazo[4,5-d]phenanthroline compounds of Formula I that are capable of intracellular chelation of transition metals and of exerting antiproliferative effects in cancer cells, that are cytostatic and/or cytotoxic, are provided. Compounds of Form

Indane or dihydroindole derivatives

The present invention relates to substituted indane or dihydroindole compounds of Formula (I) wherein A is an indole. These compounds have high affinity for D4receptors.