25519-77-1

Basic information

• Product Name: 1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE
• Synonyms: 1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE;4-(2',4'-DIFLUOROBENZOYL)-1-ACETYLPIPERIDINE;1-acetyl-4-(4-fluorobenzoyl)piperidine;Ethanone, 1-[4-(4-fluorobenzoyl)-1-piperidinyl]-
• CAS NO: 25519-77-1
• Molecular Formula: C₁₄H₁₆FNO₂
• Molecular Weight: 267.27
• EINECS: 247-069-5
• Mol File: 25519-77-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 408.064 °C at 760 mmHg
• Flash Point: 200.59 °C
• Appearance: /
• Density: 1.248 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: 1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE(25519-77-1)
• EPA Substance Registry System: 1-[4-(2,4-DIFLUORO-BENZOYL)-PIPERIDIN-1-YL]-ETHANONE(25519-77-1)

Safety Data

• Hazardous Substances Data: 25519-77-1(Hazardous Substances Data)

Usage

Uses

1-[4-(2,4-Difluorobenzoyl)piperidin-1-yl]ethanone is a chemical reagent used in the synthesis of antiproliferative agents as well as for piperidines displaying 5-HT2 antagonist activity.

InChI:InChI=1/C14H15F2NO2/c1-9(18)17-6-4-10(5-7-17)14(19)12-3-2-11(15)8-13(12)16/h2-3,8,10H,4-7H2,1H3

Upstream product

• 59084-16-1 1-acetylpiperidine-4-carbonyl chloride 
• 462-06-6 fluorobenzene 
• 213886-98-7 1-acetyl-N-methoxy-N-methylpiperidine-4-carboxamide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 56346-57-7 (4-fluorophenyl)-piperidin-4-ylmethanone 
• 108-24-7 acetic anhydride 
• 498-94-2 isonipecotic acid 
• 25503-90-6 1-acetyl-piperidine-4-carboxylic acid 

Downstream Products

• 58113-20-5 1-acetyl-α-(4-fluorophenyl)-α-phenyl-4-piperidinemethanol 
• 63388-12-5 1-acetyl-4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]piperidine 
• 92822-02-1 4-(4-fluorobenzyl)piperidine 
• 193357-52-7 4-(4-fluorobenzyl)piperidine hydrobromide 
• 25519-78-2 4-(4-fluorobenzoyl)piperidine hydrochloride 
• 116796-12-4 α-(4-fluorophenyl)-α-(pyridin-2-yl)-4-piperidinemethanol 
• 142221-79-2 4-(4-fluorobenzoyl)piperidine hydrobromide 
• 131415-90-2 1-Acetyl-4-(4-morpholinobenzoyl)piperidine 
• 131415-89-9 1-acetyl-4-(4-piperidinobenzoyl)piperidine 

Relevant articles and documents

Synthesis of Novel Aryloxyethylamine Derivatives and Evaluation of Their in Vitro and in Vivo Neuroprotective Activities

A series of aryloxyethylamine derivatives were designed, synthesized and evaluated for their biological activity. Their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR and HR-ESI-MS. The preliminary screening of neuroprotection of compounds in vitro was detected by MTT, and the anti-ischemic activity in vivo was tested using bilateral common carotid artery occlusion in mice. Most of these compounds showed potential neuroprotective effects against the glutamate-induced cell death in differentiated rat pheochromocytoma cells (PC12 cells), especially for (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone, (4-bromophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone, (4-chlorophenyl)(1-{2-[(naphthalen-2-yl)oxy]ethyl}piperidin-4-yl)methanone, (4-chlorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone and {1-[2-(4-bromophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone, which exhibited potent protection of PC12 cells at three doses (0.1, 1.0, 10 μM). Compounds (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, (4-fluorophenyl){1-[2-(naphthalen-2-yloxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone and {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone possessed the significant prolongation of the survival time of mice subjected to acute cerebral ischemia and decreased the mortality rate at all five doses tested (200, 100, 50, 25, 12.5 mg/kg) and had significant neuroprotective activity. In addition, (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone and {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone possessed outstanding neuroprotection in vitro and in vivo. These compounds can be used as a promising neuroprotective agents for future development of new anti-ischemic stroke agents. Basic structure–activity relationships are also presented.

Discovery of 4-benzoylpiperidine and 3-(piperidin-4-yl)benzo[d]isoxazole derivatives as potential and selective GlyT1 inhibitors

Regulation of glycine transporter 1 (GlyT1) activity is a currently investigated strategy in drug discovery for schizophrenia. This study developed a series of new 4-benzoylpiperidine derivatives as GlyT1 inhibitors by bioisosteric replacement and mimicking of the pyridine ring of RG1678. Among the 4-benzoylpiperidine derivatives, 23q showed an IC50 of 30 nM. Preliminary optimization of the blood-brain barrier penetration led to the discovery of 3-(piperidin-4-yl)benzo[d]isoxazole derivatives. Both series showed good selectivity over GlyT2, D1, D2, D3, 5-HT1A and 5-HT2A receptors. Moreover, behavioral testing showed 23q (40 mg kg-1, intragastric) can inhibit the hyperlocomotion induced by acute treatment of phencyclidine, and improve the impaired negative and cognitive symptoms in chronic phencyclidine-induced C57BL/6J mice. An interesting finding showed that 3-(piperidin-4-yl)benzo[d]isoxazole was a privileged scaffold of atypical antipsychotic agents but exhibited high selectivity and potency as a GlyT1 inhibitor.

METHYLENE LINKED QUINOLINYL MODULATORS OF ROR-GAMMA-T

The present invention comprises compounds of Formula (I). wherein: R1, R2, R3, R4, R5, R6, R7, R8, and R9 are defined in the specification. The invention also comprises a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.