126921-16-2

Basic information

• Product Name: 1H-Indole-3-carboxaldehyde,7-fluoro-
• Synonyms: 3-Formyl-7-fluoro-1H-indole;7-Fluoro-1H-indole-3-carboxaldehyde; 7-Fluoroindole-3-carboxaldehyde
• CAS NO: 126921-16-2
• Molecular Formula: C₉H₆FNO
• Molecular Weight: 163.1484
• Mol File: 126921-16-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 342.423°C at 760 mmHg
• Flash Point: 160.892°C
• Appearance: /
• Density: 1.386g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.695
• CAS DataBase Reference: 1H-Indole-3-carboxaldehyde,7-fluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-carboxaldehyde,7-fluoro-(126921-16-2)
• EPA Substance Registry System: 1H-Indole-3-carboxaldehyde,7-fluoro-(126921-16-2)

Safety Data

• Hazardous Substances Data: 126921-16-2(Hazardous Substances Data)

Usage

General Description

1H-Indole-3-carboxaldehyde, 7-fluoro- is a chemical compound with the molecular formula C9H6FNO. It is a derivative of indole, a heterocyclic aromatic compound, with the addition of a carboxaldehyde group and a fluorine atom at the 7th position. This chemical has shown potential biological activity, making it an important compound in pharmaceutical and agrochemical research. Its unique structure and reactivity make it valuable in the synthesis of various organic compounds. Additionally, the fluorine substituent can impart specific properties to the molecule, such as increased lipophilicity and stability, which can be advantageous in drug design and development.

InChI:InChI=1/C9H6FNO/c10-8-3-1-2-7-6(5-12)4-11-9(7)8/h1-5,11H

Upstream product

• 387-44-0 7-fluoro-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 645418-84-4 2-[(7-fluoro-1H-indol-3-ylmethyl)-amino]-benzoic acid 
• 1195785-07-9 2-fluoro-6-(3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)aniline 
• 1195785-01-3 C₁₈H₁₃FN₄ 
• 1422432-56-1 C₂₁H₁₆FN₃O₃ 
• 1422433-19-9 C₂₃H₂₀FN₃O₃ 
• 863407-45-8 trans-3-[7-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide 
• 863407-40-3 [7-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde 

Relevant articles and documents

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

Discovery of a highly selective FLT3 kinase inhibitor from phenotypic cell viability profiling

We discovered a novel molecular framework 4 containing a heterobiaryl pyrazolopyridine moiety as a selective FLT3 kinase inhibitor from phenotype-based viability profiling. Compound 4g showed outstanding selectivity in cellular cytotoxicity against MV-4-11 leukemic cells via the induction of apoptosis. The hypothesis-driven deconvolution elucidated that compound 4g selectively blocked the phosphorylation of FLT3 and its downstream effectors, such as ERK and STAT5, only in MV-4-11 cells. The inhibitory effect of 4g on in vitro enzyme function and FLT3 phosphorylation in cells proved that FLT3 kinase is a direct molecular target of 4g. Finally, the kinase activity profiling of 4g verified its excellent selectivity toward FLT3 over 40 representative kinases, including the receptor tyrosine kinase (RTK) family. The Royal Society of Chemistry 2013.

An efficient one-step synthesis of heterobiaryl pyrazolo[3,4-u] pyridines via indole ring opening

A mild one-step synthetic method to access privileged heterobiaryl pyrazolo[3,4-b]pyridines from indole-3-carboxaldehyde derivatives and a variety of aminopyrazoles has been developed. This novel method constructs heterobiaryls with the wide scope of substrate generality and excellent regioselectivity via indole ring opening.