180161-14-2

Basic information

• Product Name: 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE
• Synonyms: 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE;1H-Indole, 6-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-;6-Fluoro-3-(1,2,3,6-tetrahydro-4-pyridyl)indole
• CAS NO: 180161-14-2
• Molecular Formula: C₁₃H₁₃FN₂
• Molecular Weight: 216.25
• Mol File: 180161-14-2.mol
• Article Data: 9

Chemical Properties

• Appearance: Yellow to brown/Solid
• CAS DataBase Reference: 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(180161-14-2)
• EPA Substance Registry System: 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(180161-14-2)

Safety Data

• Hazardous Substances Data: 180161-14-2(Hazardous Substances Data)

Usage

Description

6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is a chemical compound characterized by the presence of a fluorine atom, a tetrahydro-pyridinyl group, and an indole ring structure. This unique molecular architecture endows it with potential biological activity, making it a valuable asset in pharmaceutical research and drug development. Its fluorine substitution and structural features contribute to its versatility as a building block for the synthesis of new drug candidates.

Uses

Used in Pharmaceutical Research and Drug Development:
6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is used as a key intermediate in the synthesis of new drug candidates due to its potential biological activity and unique structural features.
Used in Anticancer Drug Development:
In the pharmaceutical industry, 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is used as a precursor for the development of novel anticancer drugs, leveraging its potential to target and inhibit specific cancer-related pathways.
Used in Antimicrobial Drug Development:
6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is utilized as a component in the creation of new antimicrobial agents, capitalizing on its ability to combat resistant microbial strains.
Used in Neurological Drug Development:
6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is employed as a building block for the development of neurological drugs, aiming to address various neurological disorders and conditions by modulating specific neurotransmitter systems or receptors.
Used in Biological Research:
6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is used as a chemical tool in biological research to probe and understand complex biological systems, offering insights into the mechanisms of disease and potential therapeutic targets.
The diverse potential applications of 6-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE make it a compound of significant interest to researchers in the pharmaceutical and biomedical fields, as it holds promise for advancing the development of innovative treatments and diagnostic tools.

Upstream product

• 399-51-9 6-fluoro-1H-indole 
• 41979-39-9 4-piperidone hydrochloride 
• 41661-47-6 piperidin-4-one 
• 40064-34-4 4-piperidone monohydrochloride monohydrate 
• 255724-68-6 2-ethynyl-5-fluoroaniline 
• 255724-71-1 5-fluoro-2-iodoaniline 

Downstream Products

• 180160-70-7 7-chloro-3-(piperidin-4-yl)-1H-indole 
• 76315-55-4 6-fluoro-3-(piperidin-4-yl)-1H-indole 
• 223521-24-2 N-(2-(4-(2-methoxyphenyl)piperazin-1-yl)eth-1-yl)-3-(4-(6-fluoroindol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl)propanamide 

Relevant articles and documents

Synthesis and structure-activity relationships of novel histamine H 1 antagonists: Indolylpiperidinyl benzoic acid derivatives

A series of indolylpiperidinyl derivatives were prepared and evaluated for their activity as histamine H1 antagonists. Structure-activity relationship studies were directed toward improving in vivo activity and pharmacokinetic profile of our first lead (1). Substitution of fluorine in position 6 on the indolyl ring led to higher in vivo activity in the inhibition of histamine-induced cutaneous vascular permeability assay but lower selectivity toward 5HT2 receptor. Extensive optimization was carried out within this series and a number of histamine H1 antagonists showing potency and long duration of action in vivo and low brain penetration or cardiotoxic potential were identified. Within this novel series, indolylpiperidines 15, 20, 48, 51 and 52 exhibited a long half-life in rat and have been selected for further preclinical evaluation.

PHARMACEUTICAL COMPOUNDS

A pharmaceutical compound of the formula in which R1 is hydrogen, C1-4 alkyl, C1-4 alkoxy or halo, and R2 is hydrogen, C1-4 alkyl or C1-4 alkoxy; or a salt thereof.

Neighboring group participation of the indole nucleus: An unusual DAST-mediated rearrangerment reaction

A rearrangement reaction involving the indole nucleus was investigated using stereochemical markers and low-temperature NMR experiments. Treatment of(3S,4S)-3-hydroxy-4-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with diethylaminosulfur trifluoride gave stereospecifically (3S,4S)-4-fluoro-3-(2-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester (> 90% ee) with complete regioselectivity. The initial formation of a reactive spirocyclopropyl-3H-indole intermediate is believed to be responsible for the stereo- and regiochemical outcome of the reaction.