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421626

Sigma-Aldrich

(S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid

97%

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Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
74163-81-8
Molecular Weight:
177.20
Beilstein:
4842199
MDL number:
MFCD00144533
UNSPSC Code:
12352106
PubChem Substance ID:
24866388
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

optical activity

[α]20/D −168°, c = 1.8 in 1.4 M NaOH

reaction suitability

reaction type: solution phase peptide synthesis

mp

>300 °C (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)[C@@H]1Cc2ccccc2CN1

InChI

1S/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-/m0/s1

InChI key

BWKMGYQJPOAASG-VIFPVBQESA-N

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Related Categories

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Kazuya Otake et al.
Chemical & pharmaceutical bulletin, 59(10), 1233-1242 (2011-10-04)
Novel 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives were synthesized and (S)-7-(2-{2-[(E)-2-cyclopentylvinyl]-5-methyloxazol-4-yl}ethoxy)-2-[(2E,4E)-hexadienoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (14c) was identified as a peroxisome proliferator-activated receptor (PPAR) α/γ dual agonist. The transactivation activity of 14c was comparable to that of rosiglitazone in human PPARγ (EC50=0.14 µM) and was much
Kazuya Otake et al.
Chemical & pharmaceutical bulletin, 59(7), 876-879 (2011-07-02)
2-Acyl-tetrahydroisoquinoline-3-carboxylic acid derivatives were synthesized and biologically evaluated. (S)-2-(2,4-Hexadienoyl)-7-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (14) showed peroxisome proliferator-activated receptor γ (PPARγ) and PPARα agonist activities and protein-tyrosine phosphatase 1B (PTP-1B) inhibitory activities. PPARγ agonist activity of 14 was comparable to that of rosiglitazone, and
P Majer et al.
International journal of peptide and protein research, 43(1), 62-68 (1994-01-01)
A new method of synthesizing ortho-methylated phenylalanines has been developed. Phenylalanines with at least one free ortho-position undergo a Pictet-Spengler cyclization with formaldehyde followed by hydrogenolytic splitting of the endocyclic benzylic C--N bond of 1,2,3,4-tetrahydroisoquinolines and afford corresponding ortho-methyl derivatives.
Zinovia Spyranti et al.
Amino acids, 39(2), 539-548 (2010-01-29)
Incorporation of L- or D-Tic into position 7 of oxytocin (OT) and its deamino analogue ([Mpa(1)]OT) resulted in four analogues, [L-Tic(7)]OT (1), [D-Tic(7)]OT (2), [Mpa(1),L-Tic(7)]OT (3) and [Mpa(1),D-Tic(7)]OT (4). Their biological properties were described by Fragiadaki et al. (Eur J
Bradford H Hirth et al.
Bioorganic & medicinal chemistry letters, 15(8), 2087-2091 (2005-04-06)
A series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid diamides that increase chloride transport in cells expressing mutant cystic fibrosis transmembrane conductance regulator (CFTR) protein has been identified from our compound library. Analoging efforts and the resulting structure-activity relationships uncovered are detailed. Compound potency
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