134732-98-2

Usage

Uses

Used in Chemical Synthesis:
(3S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxamide is used as an organocatalyst for asymmetric aldol reactions. As an organocatalyst, it plays a crucial role in facilitating the selective formation of chiral molecules, which are essential in the pharmaceutical industry for the production of enantiomerically pure drugs. The compound's ability to induce asymmetry in chemical reactions makes it a valuable tool in the synthesis of complex organic molecules with specific stereochemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide is used as a key intermediate in the synthesis of various drugs. Its unique structural features allow for the development of new drug candidates with potential therapeutic applications. The compound's reactivity and stereochemistry can be exploited to create novel molecules with improved pharmacological properties, such as increased potency, selectivity, and reduced side effects.
Used in Research and Development:
(3S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxamide is also utilized in research and development for the study of various chemical reactions and processes. Its application as an organocatalyst in asymmetric aldol reactions provides valuable insights into the mechanisms of enantioselective catalysis, which is essential for the advancement of synthetic methodologies and the development of new chiral compounds with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 150417-15-5 (S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 79815-19-3 methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate 
• 77497-96-2 (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester 
• 77497-97-3 benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt 
• 78183-55-8 (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride 
• 74163-81-8 L-Tic-OH 
• 115962-35-1 (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid 

Downstream Products

• 854113-37-4 [3-((3R)-3-carbamoyl-3,4-dihydro-1H-isoquinoline-2-yl)-1-(2-fluoro-benzyl)-3-oxopropyl]-carbamic acid tert-butyl ester 
• 1238366-03-4 C₁₈H₁₈N₂O₃ 
• 54329-61-2 3-aminomethyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride 

Relevant academic research and scientific papers

Towards novel 5-HT7 versus 5-HT1A receptor ligands among LCAPs with cyclic amino acid amide fragments: Design, synthesis, and antidepressant properties. Part II

A 26-membered library of novel long-chain arylpiperazines, which contained primary and tertiary amides of cyclic amino acids (proline and 1,2,3,4-tetrahydroisoquinoline-3-carboxamide) in the terminal fragment was synthesized and biologically evaluated for binding affinity for 5-HT7 and 5-HT1A receptors. Docking studies confirmed advantages of Tic-amide over Pro-amide fragment for interaction with 5-HT7 receptors. Selected compounds 32 and 28, which behaved as 5-HT7Rs antagonist and 5-HT1A partial agonist, respectively, produced antidepressant-like effects in the forced swim test in mice after acute treatment in doses of 10 mg/kg (32) and 1.25 mg/kg (28). Compound 32 reduced immobility in a manner similar to the selective 5-HT7 antagonist SB-269970.

Synthesis and characterization of n-substituted (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides as organocatalysts for asymmetric aldol reaction

In this paper, the preparation and characterization of eight optically pure N-functionalized (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides is described. The prepared amides and thioamides were tested as organocatalysts of aldol reaction of 4-nitrobenzaldehyde and acetone. The highest ee of formation of 4-hydroxy-4-(4-nitrophenyl)butan-2-one was obtained with (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (77% ee). The observed deceleration of the aldol reaction catalyzed in this way, as compared with that catalyzed with (S)-proline, was attributed to the formation of little reactive cyclic intermediate, which was isolated and characterized.

Synthesis of (S)-3-aminoethyl-1,2,3,4-tetrahydroisoquinoline (TIQ-diamine) via the Mitsunobu protocol

The synthesis of (S)-3-Aminoethyl-1, 2, 3, 4-tetrahydroisoquinoline (TIQ-diamine) was successfully achieved via the Mitsunobu protocol. The method from earlier reports utilizing aminolysis of commercially available TIQ-amino methyl ester, and reduction of

Synthesis of tetrahydroisoquinoline-diamine ligands and their application in asymmetric transfer hydrogenation

The use of the tetrahydroisoquinoline scaffold is well documented in biologically active compounds. However, reports of the utilisation of tetrahydroisoquinoline compounds in asymmetric catalysis are limited. The synthesis of novel diamine ligands possessing the tetrahydroisoquinoline (tetrahydroisoquinoline) backbone and evaluation of their activity in the asymmetric transfer hydrogenation of acetophenone are presented. The diamine ligands in conjunction with i-PrOH as the hydrogen source and [RhCl2(Cp*)]2 as the metal precursor proved to be the most effective of the tetrahydroisoquinoline derivatives for this catalytic system. Water was found to have a profound influence on the enantioselectivity of the reaction. Optimisation of the amount water, i-PrOH and catalytic loading content rendered the best result of 70% enantioselectivity for the (S)-1-phenylethanol isomer product.

The reversed binding of β-phenethylamine inhibitors of DPP-IV: X-ray structures and properties of novel fragment and elaborated inhibitors

The co-crystal structure of β-phenethylamine fragment inhibitor 5 bound to DPP-IV revealed that the phenyl ring occupied the proline pocket of the enzyme. This finding provided the basis for a general hypothesis of a reverse binding mode for β-phenethylam

Optimized synthesis of tetrahydroisoquinoline-hydantoins

Several methods have been developed and compared for the solution synthesis of tetrahydroisoquinoline-hydantoin derivatives. The best yields were obtained when the imidazolidine-2,4-dione ring was synthesized in two steps: (1) reaction of Tic-OH with the appropriate amine and (2) cyclization with 1,1′-carbonyldiimidazole.