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 
• 89047-45-0 quinoline-2-carboxylic acid hydrochloride 
• 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 

Downstream Products

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 4620-34-2 ethyl 1,2,3,4-tetrahydroquinoline-2-carboxylate 
• 123811-87-0 1-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 
• 75493-94-6 (S)-(-)-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 
• 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 
• 618113-62-5 2-Iodomethyl-1,2,3,4-tetrahydro-quinoline 
• 63492-82-0 methyl (2S)-1,2,3,4-tetrahydroquinoline-2-carboxylate 
• 63492-81-9 methyl (2R)-1,2,3,4-tetrahydroquinoline-2-carboxylate 
• 150533-87-2 6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione 
• 185854-45-9 2-(1,2,3,4-tetrahydroquinolin-2-yl)acetic acid 

Relevant articles and documents

Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer

Prostate cancer (PC) is the most common malignancy in men worldwide. Here, two series of novel thiohydantoin derivatives of enzalutamide as potent androgen receptor (AR) antagonists were designed and synthesized. Among them, compound 31c was identified as an AR antagonist which is 2.3–fold more potent than enzalutamide. Molecular docking studies were performed to explain the improved potency of 31c at AR. In cell proliferation assays, 31c exhibited similar anti-proliferative activities with enzalutamide against hormone sensitive LNCaP cells and AR-overexpressing LNCaP/AR cells. These data indicate that 31c can be a good lead compound for further structure optimization for the treatment of prostate cancer.

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.

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

Targeting dopamine D3 and serotonin 5-HT1A and 5-HT2A receptors for developing effective antipsychotics: Synthesis, biological characterization, and behavioral studies

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.

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

Design, synthesis, and evaluation of tetrahydroquinoline and pyrrolidine sulfonamide carbamates as γ-secretase inhibitors

γ-Secretase is a key enzyme involved in the production of β-amyloid peptides which are believed to play a critical role in the onset and progression of Alzheimer's disease (AD). As such, inhibition of γ-secretase has been an attractive approach to AD ther

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

A series of tetrahydroqninoline-linked thiazolidinediones was designed and synthesized and their peroxisome proliferator activated receptor-γ (PPARγ) agonistic activities were evaluated. A number of analogs were revealed to have significant PPARγ agonisti

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.

Fused bicyclic carboxamide derivatives and methods of their use

Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.

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.