127626-06-6

Basic information

• Product Name: 5-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE
• Synonyms: 5-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE;5-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-Indole
• CAS NO: 127626-06-6
• Molecular Formula: C₁₃H₁₃FN₂
• Molecular Weight: 216.2541232
• Mol File: 127626-06-6.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(127626-06-6)
• EPA Substance Registry System: 5-FLUORO-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(127626-06-6)

Safety Data

• Hazardous Substances Data: 127626-06-6(Hazardous Substances Data)

Upstream product

• 41661-47-6 piperidin-4-one 
• 399-52-0 5-fluoro-1H-indole 
• 40064-34-4 4-piperidone monohydrochloride monohydrate 
• 41979-39-9 4-piperidone hydrochloride 

Downstream Products

• 149669-43-2 5-fluoro-3-(piperidin-4-yl)-1H-indole 
• 1365043-77-1 N-{4-[4-(5-fluoro-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]butyl}-3-methylbenzene-1-sulfonamide 
• 1365043-87-3 N-{2-[4-(5-fluoro-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]ethyl}-3-methylbenzene-1-sulfonamide 

Relevant articles and documents

Synthesis and biological evaluation of novel pyrrolidine-2,5-dione derivatives as potential antidepressant agents. Part 1

A series of 3-(1H-indol-3-yl)pyrrolidine-2,5-dione derivatives was synthesized and their biological activity was evaluated. The chemical structures of the newly prepared compounds were confirmed by 1H NMR, 13C NMR and ESI-HRMS spectra data. All tested compounds proved to be potent 5-HT1A receptor and serotonin transporter protein (SERT) ligands. Among them, compounds 15, 18, 19 and 30 showed significant affinity for 5-HT1A and SERT. Computer docking simulations carried out for compounds 15, 31 and 32 to models of 5-HT1A receptor and SERT confirm the results of biological tests. Due to high affinity for the 5-HT1A receptor and moderate affinity for SERT, compounds 31, 32, 35, and 37 were evaluated for their affinity for D2L, 5-HT6, 5-HT 7 and 5-HT2A receptors. In vivo tests, in turn, resulted in determining the functional activity of compounds 15, 18, 19 and 30 to the 5-HT1A receptor. The results of these tests indicate that all of the ligands possess properties characteristic of 5-HT1A receptor agonists.

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.

3-Tetrahydropyridin-4-yl indoles for treatment of psychotic disorders

The invention is related to the following compounds: wherein all variables are as defined in the specification. The compounds are useful for treating psychotic disorders.