92977-00-9

Basic information

• Product Name: (R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID
• Synonyms: (R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID;D-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID;2-QUINOLINECARBOXYLIC ACID, 1, 2, 3, 4 - TETRAHYDR;REF DUPL: D-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid;2-Quinolinecarboxylic acid, 1,2,3,4-tetrahydro-, (2R)-;(2R)-1,2,3,4-Tetrahydro-2-quinolinecarboxylic acid
• CAS NO: 92977-00-9
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.2
• Mol File: 92977-00-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID(92977-00-9)
• EPA Substance Registry System: (R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID(92977-00-9)

Safety Data

• Hazardous Substances Data: 92977-00-9(Hazardous Substances Data)

Usage

General Description

The chemical compound (R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid is a quinoline derivative that consists of a tetrahydroquinoline core with a carboxylic acid functional group at the 2-position. It is a chiral molecule that exists in two enantiomeric forms, with the (R)-enantiomer being the specific form described in the compound name. (R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID has potential applications in organic synthesis, medicinal chemistry, and as a building block for the preparation of various pharmaceuticals and bioactive compounds. It may also possess biological activity and could be investigated for its potential pharmacological properties.

Upstream product

• 63430-79-5 1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester 
• 93-10-7 quinoline-2-carboxylic acid 
• 46185-24-4 1,2,3,4-tetrahydroquinoline-2-carboxylic acid 
• 290310-87-1 (R)-1-Benzoyl-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid amide 
• 290310-86-0 (R)-1-Benzoyl-1,2,3,4-tetrahydro-quinoline-2-carbonitrile 
• 290310-81-5 (R)-1-Benzoyl-1,2-dihydro-quinoline-2-carbonitrile 
• 290310-73-5 (R)-N-(2-furoyl)-2-cyano-1,2-dihydroquinoline 
• 91-22-5 quinoline 

Downstream Products

• 898533-10-3 (R)-(+)-N-[4-(4-phenylpiperazin-1-yl)butyl]-1,2,3,4-tetrahydroquinoline-2-carboxamide 
• 898533-06-7 (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1,2,3,4-tetrahydroquinoline-2-carboxamide 
• 898533-09-0 (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide 
• 75493-95-7 (R)-(+)-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 
• 63492-81-9 methyl (2R)-1,2,3,4-tetrahydroquinoline-2-carboxylate 

Relevant articles and documents

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.

Catalytic enantioselective reissert-type reaction: Development and application to the synthesis of a potent NMDA receptor antagonist (-)-L-689,560 using a solid-supported catalyst

Full details of the first catalytic enantioselective Reissert-type reaction are described. Utilizing the Lewis acid-Lewis base bifunctional catalyst 5 or 6 (9 mol %), the Reissert products were obtained in 57 to 99% yield with 54 to 96% ee. Electron-rich

Enzymatic resolution of 2-substituted tetrahydroquinolines. Convenient approaches to tricyclic quinoxalinediones as potent NMDA-glycine antagonists

Two approaches leading to the enantiomerically pure tricyclic quinoxalinedione class of NMDA-glycine antagonists using enzymatic resolutions are described. An intermediate, racemic methyl 1,2,3,4- tetrahydroquinoline-2-carboxylate 3, was resolved to (S)-3