46185-24-4

Basic information

• Product Name: 1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID
• Synonyms: 1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID;2-Quinolinecarboxylic acid, 1,2,3,4-tetrahydro-;1,2,3,4-tetrahydro-2-Quinolinecarboxylic acid
• CAS NO: 46185-24-4
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Mol File: 46185-24-4.mol

Chemical Properties

• Melting Point: 112-113 °C
• Boiling Point: 392.598 °C at 760 mmHg
• Flash Point: 191.237 °C
• Appearance: /
• Density: 1.225
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: 2-8°C
• PKA: 2.15±0.20(Predicted)
• CAS DataBase Reference: 1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID(46185-24-4)
• EPA Substance Registry System: 1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID(46185-24-4)

Safety Data

• Hazardous Substances Data: 46185-24-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydroquinoline-2-carboxylic acid is used as a chemical reagent for the production of Indoline-2-carboxamide derivatives. These derivatives are brain-penetrant inhibitors of Trypanosoma brucei, a parasite responsible for African trypanosomiasis, also known as sleeping sickness. The development of such inhibitors is crucial for the treatment of this disease, as they can cross the blood-brain barrier and target the parasite in the central nervous system.
Additionally, due to its unique structure and properties, 1,2,3,4-tetrahydroquinoline-2-carboxylic acid may also be utilized in the synthesis of other bioactive compounds and pharmaceuticals, contributing to the advancement of drug discovery and development in various therapeutic areas.

InChI:InChI=1/C10H11NO2/c12-10(13)9-6-5-7-3-1-2-4-8(7)11-9/h1-4,9,11H,5-6H2,(H,12,13)

Upstream product

• 93-10-7 quinoline-2-carboxylic acid 
• 91-63-4 2-methylquinoline 
• 5470-96-2 quinoline 2-carbaldehyde 
• 1133419-06-3 1,2,3,4-tetrahydro-quinoline-2-carboxylic acid ethyl ester hydrochloride 
• 89047-45-0 quinoline-2-carboxylic acid hydrochloride 

Downstream Products

• 75493-94-6 (S)-(-)-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 
• 63430-79-5 1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester 
• 219948-39-7 4,5-dihydro-3-oxido-2-[4-(trifluoromethyl)phenyl]-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219948-75-1 4,5-dihydro-3-oxido-2-[4-(trifluoromethoxy)phenyl]-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219949-11-8 4,5-dihydro-3-oxido-2-(3-trifluoromethylphenyl)-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219948-76-2 4,5-dihydro-3-oxido-2-phenyl-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219948-68-2 4,5-dihydro-3-oxido-2-(4-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219948-79-5 3-oxo-2-phenyl-2,3-dihydro-[1,2,3]triazolo[1,5-a]quinolin-10-ium-1-ide 
• 219948-72-8 2-(4-fluorophenyl)-3-oxido-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219948-45-5 3-oxido-2-[4-(trifluoromethyl)phenyl]-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219949-13-0 3-oxido-2-[3-(trifluoromethyl)phenyl]-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219948-77-3 3-oxido-2-[4-(trifluoromethoxy)phenyl]-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 219948-81-9 5-bromo-3-oxido-2-[4-(trifluoromethoxy)phenyl]-[1,2,3]triazolo[1,5-a]quinolinium inner salt 
• 123811-88-1 3,4-Dihydro-2H-quinoline-1,2-dicarboxylic acid 1-tert-butyl ester; compound with dicyclohexyl-amine 

Relevant articles and documents

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PHTHALAZINE DERIVATIVES OF FORMULA (I) AS PCAF AND GCN5 INHIBITORS FOR USE IN THE TREATMENT OF CANCER

The present invention relates to methods for treating PCAF and GCN5 mediated disorders using a compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein ring A, R1, R3, R4, R5, and each Re have any of the values defined in the specification. Also included are novel compounds of Formula (I) and salts thereof, as well as pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof.

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Combination of dopamine D3 antagonism, serotonin 5-HT1A partial agonism, and antagonism at 5-HT2A leads to a novel approach to potent atypical antipsychotics. Exploitation of the original structure-activity relationships resulted in the identification of safe and effective antipsychotics devoid of extrapyramidal symptoms liability, sedation, and catalepsy. The potential atypical antipsychotic 5bb was selected for further pharmacological investigation. The distribution of c-fos positive cells in the ventral striatum confirmed the atypical antipsychotic profile of 5bb in agreement with behavioral rodent studies. 5bb administered orally demonstrated a biphasic effect on the MK801-induced hyperactivity at dose levels not able to induce sedation, catalepsy, or learning impairment in passive avoidance. In microdialysis studies, 5bb increased the dopamine efflux in the medial prefrontal cortex. Thus, 5bb represents a valuable lead for the development of atypical antipsychotics endowed with a unique pharmacological profile for addressing negative symptoms and cognitive deficits in schizophrenia.

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Design, synthesis, and evaluation of tetrahydroquinoline-linked thiazolidinedione derivatives as pparγ selective activators

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Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists

In the course of continuing efforts to develop potent and bladder-selective muscarinic M3 receptor antagonists, quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives and related compounds were designed as conformationally restricted analogues of quinuclidin-3-yl benzhydrylcarbamate (8). Binding assays with rat muscarinic receptor subtypes revealed that the quinuclidin-3-yl 1-aryl-1,2,3,4- tetrahydroisoquinoline-2-carboxylate derivatives showed high affinities for the M3 receptor, and selectivity for the M3 receptor over the M2 receptor. Of these derivatives, (+)-(1S,3'R)-quinuclidin-3'-yl 1-phenyl-l,2,3,4-tetrahydroisoquinoline-2-carboxylate monohydrochloride (9b) exhibited almost the same inhibitory activity against bladder contraction to that of oxybutynin (1), and more than 10-fold selectivity for bladder contraction versus salivary secretion, demonstrating that 9b may be useful for the treatment of symptoms associated with overactive bladder without having side effects such as dry mouth.

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Solvent dependent regioselective hydrogenation of substituted quinolines

Various substituted quinolines have been reduced under H2 using Rh/Al2O3. Using methanol as solvent leads selectively to the 1,2,3,4-tetrahydroquinoline derivatives whereas in hexafluoroisopropanol the decahydro compounds are obtained.