103733-65-9

Basic information

• Product Name: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
• Synonyms: 1,2,3,4-TETRAHYDROISOQUINOLINE-(3R)-CARBOXYLIC ACID;1,2,3,4-D-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;3-ISOQUINOLINECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-, (3R)-;(3R)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;H-D-TIC-OH;D-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;D-[3R]-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;D-TIC
• CAS NO: 103733-65-9
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: 266-580-4
• Product Categories: Amino Acids;Others;Peptide Synthesis;Unnatural Amino Acid Derivatives;a-amino
• Mol File: 103733-65-9.mol

Chemical Properties

• Melting Point: 320-323 °C (decomp)
• Boiling Point: 372 ºC at 760 mmHg
• Flash Point: 178.8 ºC
• Appearance: White/Crystalline Powder
• Density: 1.225 g/cm³
• Vapor Pressure: 3.41E-06mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly), Aqueous Base (Sparingly, Sonicated)
• PKA: 2.21±0.20(Predicted)
• CAS DataBase Reference: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(103733-65-9)
• EPA Substance Registry System: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(103733-65-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 103733-65-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is used as an amino acid building block for peptide synthesis. The growing peptide drug market necessitates the fast and reliable synthesis of peptides, making this compound an essential component in the development of new medications.
Used in Biotechnology Industry:
In the biotechnology sector, D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid serves as a vital component in the creation of bioactive peptides. These peptides have potential applications in various fields, including therapeutics, diagnostics, and research, further emphasizing the importance of this compound in advancing biotechnological innovations.

InChI:InChI=1/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)/t9-/m1/s1

Upstream product

• 50-00-0 formaldehyd 
• 673-06-3 D-(R)-phenylalanine 
• 74163-81-8 L-Tic-OH 
• 146503-35-7 benzyl (3R)-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 143767-57-1 (-)-menthyl (R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 307304-56-9 (3'S,4R,5S)-1,5-dimethyl-4-phenyl-3-(1',2',3',4'-tetrahydro-3'-isoquinolinylcarbonyl)-2-imidazolidinone 
• 307304-64-9 (3'R,4S,5R)-1,5-dimethyl-4-phenyl-3-(1',2',3',4'-tetrahydro-3'-isoquinolinylcarbonyl)-2-imidazolidinone 
• 67123-97-1 (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 143767-54-8 (R,S)-2-acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 612-12-4 o-Xylylene dichloride 
• 143767-55-9 dimethyl 2-acetyl-1,2,3,4-tetrahydroisoquinoline-3,3-dicarboxylate 
• 91-13-4 α,α'-dibromo-o-xylene 
• 115-11-7 isobutene 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 

Downstream Products

• 77708-84-0 (S)-2-(3-Acetylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid 
• 77708-84-0 N-(3'-Acetylthio-2'-methylpropanoyl)-L-(1,2,3,4-tetrahydroisoquinoline)-3-carboxylic acid 
• 115732-14-4 N-benzoyl-D-3-carboxy-1,2,3,4-tetrahydroisoquinoline 
• 103733-65-9 (R)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester 
• 62855-02-1 (R)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline 
• 191326-92-8 (3R)-N-(4-biphenylylsulfonyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid 

Relevant articles and documents

Characterization of a selective inhibitor for matrix metalloproteinase-8 (MMP-8)

MMP-8 has been implicated in various diseases. Selective MMP-8 inhibitors are needed to ascertain the role of this enzyme. We synthesized two inhibitors reported previously as selective for MMP-8. Compound 1 selectively inhibited MMP-8 and MMP-13; compoun

Asymmetric Transformation of (RS)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic Acid via Salt Formation with (1S)-10-Camphorsulfonic Acid

Asymmetric transformation of (RS)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid by use of (1S)-10-camphorsulfonic acid as a resolving agent gave a salt of (S)-TIC with (S)-CS with 90percent optical purity in hexanoic acid.The TIC obtained from the salt was purified to give optically pure (S)-TIC in 80percent yield based on the starting (RS)-TIC.

Concise, catalytic asymmetric synthesis of tetrahydroisoquinoline- and dihydroisoquinoline-3-carboxylic acid derivatives

Catalytic asymmetric synthesis of tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives 1 has been accomplished by the successful utilization of phase-transfer catalysis of the C2-symmetric chiral quaternary ammonium bromides. Our approach also enables facile synthesis of quaternary isoquinoline derivatives 2 and 3 with high enantiomeric purities.

Tetrahydroisoquinoline derivatives as highly selective and potent rho kinase inhibitors

Rho kinase (ROCK) is a promising drug target for the treatment of many diseases including hypertension, multiple sclerosis, cancer, and glaucoma. The structure-activity relationships (SAR) around a series of tetrahydroisoquinolines were evaluated utilizing biochemical and cell-based assays to measure ROCK inhibition. These novel ROCK inhibitors possess high potency, high selectivity, and appropriate pharmacokinetic properties for glaucoma applications. The lead compound, 35, had subnanomolar potency in enzyme ROCK-II assays as well as excellent cell-based potency (IC50 = 51 nM). In a kinase panel profiling, 35 had an off-target hit rate of only 1.6% against 442 kinases. Pharmacology studies showed that compound 35 was efficacious in reducing intraocular pressure (IOP) in rats with reasonably long duration of action. These results suggest that compound 35 may serve as a promising agent for further development in the treatment of glaucoma. 2010 American Chemical Society. r2010 American Chemical Society.

ANTIPARASITIC TERPENE ALKALOIDS

The present invention relates to novel terpene alkaloids and their use as antiparasitic agents. The present invention also relates to an antiparasitic agent which comprises a terpene alkaloid compound of this invention as an effective ingredient in an antiparasitic formulation. More particularly, the present invention relates to derivatives of the terpene alkaloid (1S,2R,4aS,5R,8R,8aR)-2-(acetyloxy)-8a-hydroxy-3,8-dimethyl-5-(1-methylethenyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate. Pharmaceutical compositions comprising the same are also disclosed.

Sulfonamide derivative as a matrix metalloproteinase inhibitor

The present invention provides a novel sulfonamide derivative of general formula (I) useful as an inhibitor of matrix metalloproteinase (MMP), its isomers, pharmaceutically acceptable salts thereof and a process for preparing the same. Since the sulfonami

1,5-dimethyl-4-phenylimidazolidin-2-one-derived iminic glycinimides: Useful new reagents for practical asymmetric synthesis of α-amino acids

New 1,5-dimethyl-4-phenylimidazolidin-2-one-derived acyclic chiral iminic glycine reagents have been prepared and diastereoselectively alkylated with activated alkyl halides and electrophilic olefins in the presence of lithium chloride under (a) strong bases (LHMDS, KOBu(t)) and low temperature (-78 °C,) conditions; (b) solid-liquid phase-transfer catalysis reaction (LiOH, TBAB, -20 °C) conditions, and (c) in the presence of organic bases (DBU, BEMP, TMG, -20 °C). In the case of dielectrophiles C- and N-alkylation takes place to afford heterocyclic derivatives. Hydrolysis of alkylated products has been carried out (a) in two-step procedures with LiOOH or LiOH followed by acidic hydrolysis or Dowex purification, (b) in one single-step under refluxing water to give the corresponding α-amino acid, (c) in the presence of DBU in methanol to provide N-protected α-amino acids methyl esters, or (d) by a protection-hydrolysis procedure to afford N-Boc-protected α-amino acids. The chiral imidazolidinone has generally been recovered in good yield. This methodology has been shown to be useful for the synthesis of acyclic and heterocyclic (S)- and (R)-α-amino acids.

Efficient synthesis of racemic and enantiomerically pure 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and esters

Racemic and optically pure 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids and esters were prepared, via base-catalyzed cyclization of 1,2-bis(halomethyl)benzenes 1a or b with diethyl 2-(acetylamino)malonate (2), subsequent decarboxylation and amide cleavage. The enantiomer resolution was achieved either by esterification with (-)-menthol followed by column chromatographic separation of the diastereomeric mixture or by diasteromeric salt separation of the benzylic ester with mandelic acid and base-catalyzed saponification of both esters.

N-Acylphenylalanines and Related Compounds. A New Class of Oral Hypoglycemic Agents

N-Benzoyl-DL-phenylalanine (1) was found to possess hypoglycemic activity.A series of the analogues of compound 1 were prepared and evaluated for their blood glucose lowering activity.Both the steric effects of the phenylalanine moiety and the effects of variations in the acyl moiety were investigated.This study elucidated some of the structure-activity relationships and led to the development of N-(4-ethylbenzoyl)-D-phenylalanine (34), which was 50 times more potent than the initial compound 1.