14631-47-1

Basic information

• Product Name: 5,6,7,8-TETRAHYDRO-8-QUINOLINOL ACETATE
• Synonyms: 5,6,7,8-TETRAHYDRO-8-QUINOLINOL ACETATE;5,6,7,8-Tetrahydroquinolin-8-yl acetate;8-acetoxy-5,6,7,8-tetrahydroquinoline;Acetic acid 5,6,7,8-tetrahydro-quinolin-8-yl ester
• CAS NO: 14631-47-1
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.229
• Mol File: 14631-47-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 302.414°C at 760 mmHg
• Flash Point: 136.695°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: 2-8°C
• PKA: 5.21±0.40(Predicted)
• CAS DataBase Reference: 5,6,7,8-TETRAHYDRO-8-QUINOLINOL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-TETRAHYDRO-8-QUINOLINOL ACETATE(14631-47-1)
• EPA Substance Registry System: 5,6,7,8-TETRAHYDRO-8-QUINOLINOL ACETATE(14631-47-1)

Safety Data

• Hazardous Substances Data: 14631-47-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13NO2/c1-8(13)14-10-6-2-4-9-5-3-7-12-11(9)10/h3,5,7,10H,2,4,6H2,1H3

Upstream product

• 14631-48-2 5,6,7,8-tetrahydroquinoline N-oxide 
• 108-24-7 acetic anhydride 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 

Downstream Products

• 451466-81-2 (R)-8-hydroxy-5,6,7,8-tetrahydroquinoline 
• 14631-46-0 5,6,7,8-tetrahydroquinoline-8-ol 

Relevant articles and documents

Enantiomerically Pure Quinoline-Based κ-Opioid Receptor Agonists: Chemoenzymatic Synthesis and Pharmacological Evaluation

Racemic K-opioid receptor (KOR) agonist 2-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aSR)-8-(pyrrolidin-1-yl)-3,4,4a,5,6,7,8,8a-octahydroquinolin-1(2H)-yl]ethan-1-one ((±)-4) was prepared in a diastereoselective synthesis. The first key step of the synthesis was the diastereoselective hydrogenation of the silyl ether of 1,2,3,4-tetrahydroquinoin-8-ol ((±)-9) to afford cis,cis-configured perhydroquinoline derivative (±)-10. Removal of the TBDMS protecting group led to a β-aminoalcohol that reacted with SO2Cl2 to form an oxathiazolidine. Nucleophilic substitution with pyrrolidine resulted in the desired cis,trans-configured perhydroquinoline upon inversion of the configuration. In order to obtain enantiomerically pure KOR agonists 4 (99.8 % ee) and ent-4 (99.0 % ee), 1,2,3,4-tetrahydroquinolin-8-ols (R)-8 (99.1 % ee) and (S)-8 (98.4 % ee) were resolved by an enantioselective acetylation catalyzed by Amano lipase PS-IM. The absolute configuration was determined by CD spectroscopy. The 4aR,8S,8aS-configured enantiomer 4 showed sub-nanomolar KOR affinity (Ki=0.81 nM), which is more than 200 times higher than the KOR affinity of its enantiomer ent-4. In the cAMP assay and the Tango β-arrestin-2 recruitment assay, 4 behaved as a KOR agonist. Upon incubation of human macrophages, human dendritic cells, and mouse myeloid immune cells with 4, the number of cells expressing co-stimulatory receptor CD86 and proinflammatory cytokines interleukin 6 and tumor necrosis factor α was significantly reduced; this indicates the strong anti-inflammatory activity of 4. The anti-inflammatory effects correlated well with the KOR affinity: (4aR,8S,8aS)-4 was slightly more potent than the racemic mixture (±)-4, and the distomer ent-4 was almost inactive.

Tetrahydrobenzindole derivatives

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