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Usage

Uses

Used in Organic Synthesis:
(R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid is used as a key intermediate in the synthesis of various organic compounds. Its carboxylic acid functional group allows for a range of chemical reactions, such as esterification, amide formation, and other condensation reactions, making it a versatile building block for the creation of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (R)-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid is utilized as a starting material for the development of novel pharmaceuticals. Its unique structure and chirality may contribute to the design of new drugs with improved efficacy, selectivity, and reduced side effects.
Used in Pharmaceutical Industry:
(R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid is used as a building block for the preparation of various pharmaceuticals and bioactive compounds. Its incorporation into drug molecules can enhance their pharmacological properties, such as potency, bioavailability, and target selectivity.
Used in Biological Research:
(R)-1,2,3,4-Tetrahydro-quinoline-2-carboxylic acid is used as a subject of biological research to investigate its potential pharmacological properties. (R)-1,2,3,4-TETRAHYDRO-QUINOLINE-2-CARBOXYLIC ACID's unique structure and chirality may endow it with specific biological activities, making it a promising candidate for the development of new therapeutic agents.

Upstream product

• 290310-87-1 (R)-1-Benzoyl-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid amide 
• 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 
• 290310-86-0 (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 academic research and scientific papers

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.

Synthesis of new chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives via asymmetric hydrogenation of substituted quinolines

The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee.

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