673461-28-4

Basic information

• Product Name: (S)-N-phenyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
• Synonyms: (S)-N-phenyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
• CAS NO: 673461-28-4
• Molecular Weight: 352.433
• Mol File: 673461-28-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-N-phenyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-phenyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(673461-28-4)
• EPA Substance Registry System: (S)-N-phenyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(673461-28-4)

Safety Data

• Hazardous Substances Data: 673461-28-4(Hazardous Substances Data)

Upstream product

• 77497-96-2 (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 77497-97-3 benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt 
• 115962-35-1 (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid 
• 62-53-3 aniline 
• 74163-81-8 L-Tic-OH 

Downstream Products

• 501355-25-5 (S)-N-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1042946-25-7 (3S)-N-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide hydrochloride 

Relevant articles and documents

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.

NOVEL DIPEPTIDYL PEPTIDASE-IV INHIBITORS

The present invention relates to novel compounds exhibiting excellent inhibitory activity versus Dipeptidyl Peptidase-IV (DPP-IV), methods of preparing the same and pharmaceutical compositions containing the same as an active agent.

Synthesis and opioid activity of N,N-Dimethyl-Dmt-Tic-NH-CH(R)-R′ analogues: Acquisition of potent δ antagonism

N,N-Dimethylation of the H-Dmt-Tic-NH-CH(R)-R′ series of compounds produced no significant affect on the high δ-opioid receptor affinity (Ki=0.035-0.454 nM), but dramatically decreased that for the μ-opioid receptor. The effect of N-methylation was independent of the length of the linker (R); however, the bioactivities were affected by the chemical composition of the third aromatic group (R′): phenyl (Ph) (5′-8′) elicited a greater reduction in μ-affinity (40-70-fold) compared to analogues containing 1H-benzimidazole-2-yl (Bid) (9-fold). The major consequences of N,N-dimethylation on in vitro bioactivity were: (i) a loss of δ-agonism coupled with the appearance of potent δ antagonism (4′-7′) (pA2=8.14-9.47), while 1 exhibited only a 160-fold decreased δ agonism (1′) and the δ antagonism of 8 enhanced >10-fold (pA2=10.62, 8′); and (ii) a consistent loss of μ-affinity resulted in enhanced δ-opioid receptor selectivity. With the exception of compound 1′, the change in the hydrophobic environment at the N-terminus and formation of a tertiary amine by N,N-dimethylation in analogues of the Dmt-Tic pharmacophore produced potent δ-selective antagonists.