14631-48-2

Basic information

• Product Name: 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE
• Synonyms: 2,3-CYCLOHEXENOPYRIDINE-N-OXIDE;5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE;5,6,7,8-TETRAHYDROQUINOLINE 1-OXIDE;1-oxido-5,6,7,8-tetrahydroquinolin-1-ium
• CAS NO: 14631-48-2
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• Mol File: 14631-48-2.mol

Chemical Properties

• Melting Point: 69 °C
• Boiling Point: 358°C at 760 mmHg
• Flash Point: 170.3°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 5.42E-05mmHg at 25°C
• Refractive Index: 1.597
• PKA: 1.35±0.20(Predicted)
• CAS DataBase Reference: 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE(14631-48-2)
• EPA Substance Registry System: 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE(14631-48-2)

Safety Data

• Hazardous Substances Data: 14631-48-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
5,6,7,8-Tetrahydro-1-quinoliniumolate is used as a pharmaceutical candidate for its potential anticancer properties, as research suggests it may exhibit inhibitory effects on tumor growth and progression. It is also being studied for its neuroprotective capabilities, which could be beneficial in the treatment of neurological disorders.
Used in Organic Synthesis:
In the field of organic synthesis, 5,6,7,8-tetrahydro-1-quinoliniumolate serves as a valuable reagent in chemical reactions, contributing to the synthesis of various organic compounds.
Used in Materials Science:
5,6,7,8-Tetrahydro-1-quinoliniumolate is used in the development of new functional materials, where its unique properties can be harnessed to create innovative materials with specific applications in various industries.
Used in Chemical Reactions as a Reagent:
As a reagent, 5,6,7,8-tetrahydro-1-quinoliniumolate is employed in a variety of chemical reactions to facilitate specific transformations or to enhance the efficiency of the processes involved.

InChI:InChI=1/C9H11NO/c11-10-7-3-5-8-4-1-2-6-9(8)10/h3,5,7H,1-2,4,6H2

Upstream product

• 10500-57-9 5,6,7,8-tetrahydroquinoline 

Downstream Products

• 134220-57-8 (3aS,3bR,9aR,10aR)-5-(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-2-phenyl-3a,3b,5,6,7,8,9a,10a-octahydro-10-oxa-2,4-diaza-pentaleno[1,2-b]naphthalene-1,3-dione 
• 125162-98-3 4-Nitro-5,6,7,8-tetrahydroquinoline N-oxide 
• 150459-78-2 5,6,7,8,-tetrahydroquinoline-2-carbonitrile 
• 106057-23-2 8-chloro-5,6,7,8-tetrahydroquinoline 
• 14631-46-0 5,6,7,8-tetrahydroquinoline-8-ol 
• 912277-32-8 (R)-5,6,7,8-tetrahydroquinolin-8-yl dicyclohexylphosphinite 
• 451466-81-2 (R)-8-hydroxy-5,6,7,8-tetrahydroquinoline 
• 14631-47-1 5,6,7,8-tetrahydroquinolin-8-yl acetate 
• 1260435-69-5 (8R)-5,6,7,8-tetrahydro-8-quinolinyl (2S)-3,3,-trifluoro-2-(methyloxy)-2-phenylpropanoate 
• 1260435-66-2 (8S)-5,6,7,8-tetrahydro-8-quinolinyl (2S)-3,3,-trifluoro-2-(methyloxy)-2-phenylpropanoate 
• 1417437-47-8 2-cyclohexyl-5,6,7,8-tetrahydroquinoline 1-oxide 
• 92850-39-0 2-phenyl-5,6,7,8-tetrahydroquinoline N-oxide 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 
• 56826-69-8 5,6,7,8-tetrahydro-8-quinolinone 

Relevant articles and documents

Water-soluble inhibitors of ABCG2 (BCRP) – A fragment-based and computational approach

A good balance between hydrophilicity and lipophilicity is a prerequisite for all bioactive compounds. If the hydrophilicity of a compound is low, its solubility in water will be meager. Many drug development failures have been attributed to poor aqueous solubility. ABCG2 inhibitors are especially prone to be insoluble since they have to address the extremely large and hydrophobic multidrug binding site in ABCG2. For instance, our previous, tariquidar-related ABCG2 inhibitor UR-MB108 (1) showed high potency (79 nM), but very low aqueous solubility (78 nM). To discover novel potent ABCG2 inhibitors with improved solubility we pursued a fragment-based approach. Substructures of 1 were optimized and the fragments ‘enlarged’ to obtain inhibitors, supported by molecular docking studies. Synthesis was achieved, i.a., via Sonogashira coupling, click chemistry and amide coupling. A kinetic solubility assay revealed that 1 and most novel inhibitors did not precipitate during the short time period of the applied biological assays. The solubility of the compounds in aqueous media at equilibrium was investigated in a thermodynamic solubility assay, where UR-Ant116 (40), UR-Ant121 (41), UR-Ant131 (48) and UR-Ant132 (49) excelled with solubilities between 1 μM and 1.5 μM – an up to 19-fold improvement compared to 1. Moreover, these novel N-phenyl-chromone-2-carboxamides inhibited ABCG2 in a Hoechst 33342 transport assay with potencies in the low three-digit nanomolar range, reversed MDR in cancer cells, were non-toxic and proved stable in blood plasma. All properties make them attractive candidates for in vitro assays requiring long-term incubation and in vivo studies, both needing sufficient solubility at equilibrium. 41 and 49 were highly ABCG2-selective, a precondition for developing PET tracers. The triple ABCB1/C1/G2 inhibitor 40 qualifies for potential therapeutic applications, given the concerted role of the three transporter subtypes at many tissue barriers, e.g. the BBB.

Efficient Pyrazolo[5,4-f]quinoxaline Functionalized Os(II) Based Emitter with an Electroluminescence Peak Maximum at 811 nm

Upon fusing the pyrazinyl pyrazole entity in giving pyrazolo[3,4-f]quinoxaline chelate, the corresponding Os(II) based NIR emitter exhibited “invisible” and efficient electroluminescence with a peak maximum at 811 nm. A maximum external quantum efficiency

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.

Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides

A photoredox catalytic method has been developed for the direct C2 alkylation of pyridine N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2-alkylated pyridine N-oxides under mild conditions. Mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.

HCV PROTEASE INHIBITORS

This invention relates to the compounds of formula (I) shown below. Each variable in formula (I) is defined in the specification. These compounds can be used to treat hepatitis C virus infection.

Iridium catalysts with bicyclic pyridine-phosphinite ligands: Asymmetric hydrogenation of olefins and furan derivatives

(Chemical Equation Presented) Superior bicyclics: Iridium catalysts as 1 derived from pyridine-phosphinite ligands considerably extend the scope of asymmetric hydrogenation. In addition to various unfunctionalized and functionalized olefins, furans, and benzofurans, for which no catalysts were known before, are also hydrogenated with high enantioselectivity (see scheme).

Kinetic resolution of diols and pyridyl alcohols by cu(II)(borabox)- catalyzed acylation

Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)-catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.

1,3-BENZOTHIAZINONE DERIVATIVES AND USE THEREOF

This invention provides a compound represented by the formula (I) :wherein R1 is a hydrogen atom, a halogen atom, hydroxy, nitro, optionally halogenated alkyl, alkoxy optionally having substituents, acyl or amino optionally having substituents;R2 is pyridyl, furyl, thienyl, pyrrolyl, quinolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, tetrahydroquinolyl or thiazolyl, each of which may have substituents;n is 1 or 2; or a salt. And this invention provides a safe pharmaceutical comprising the compound of the formula (I) , which has an excellent apoptosis inhibitory effect and MIF binding effect, for preventing and/or treating heart disease, nervous degenerative disease, cerebrovascular disease, central nervous infectious disease, traumatorathy, demyelinating disease, bone and articular disease, kidney disease, liver disease, osteomyelodysplasia, AIDS, cancer, and the like.

Tetrahydrobenzindole derivatives

Compounds containing tetrahydrobenzindole which bind to serotonin receptor and are useful in treatment or prevention of disease induced by abnormality of central peripheral serotonin controlling functions.

Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the tetrasubstituted dihydroquinoline portion of siomycin D1

The tetrasubstituted dihydroquinoline portion of siomycin D1, a member of the thiostrepton family of peptide antibiotics, was synthesized from 5,6,7,8-tetrahydroquinoline featuring the modified Reissert-Henze reaction, the homolytic aromatic su