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300764

Sigma-Aldrich

1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole

98%

Synonyme(s) :

Noreleagnine, THBC, Tetrahydronorharman, Tryptoline

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About This Item

Formule empirique (notation de Hill):
C11H12N2
Numéro CAS:
16502-01-5
Poids moléculaire :
172.23
Numéro MDL:
MFCD00004954
Code UNSPSC :
12352100
ID de substance PubChem :
24857939
Nomenclature NACRES :
NA.22

Pureté

98%

Forme

liquid

Pf

206-208 °C (lit.)

Chaîne SMILES 

C1Cc2c(CN1)[nH]c3ccccc23

InChI

1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2

Clé InChI

CFTOTSJVQRFXOF-UHFFFAOYSA-N

Informations sur le gène

rat ... Htr2a(29595) , Htr2c(25187)

Description générale

Ozonolysis of the enamine bond of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole derivatives was studied.

Application

1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole was employed in alkaloid synthesis and in studies on neurodegenerative diseases.
  • Reactant for synthesis of the indolyl-β-carboline alkaloid eudistomin U via IBX mediated room temperature oxidative aromatization
  • Reactant for preparation of neuroprotective HDAC6 inhibitors
  • Reactant for preparation of aminofuranopyrimidines as EGFR and Aurora A kinase inhibitors
  • Reactant for preparation of inhibitors of CDK4
  • Reactant for preparation of tetrahydrocarboline derivatives of as human 5-HT5A receptor ligands
  • Reactant for preparation of 5-(diaminomethyl)-2,4-aminopyrimidines as dihydrofolate reductase inhibitors and antibacterial agents

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Karolina Pulka
Current opinion in drug discovery & development, 13(6), 669-684 (2010-11-10)
The synthesis of biologically active heterocyclic scaffolds is one of the significant challenges of modern synthetic chemistry. The Pictet-Spengler (PS) reaction, known for approximately a century, remains a particularly popular cyclization method. This review describes recent applications of the PS
Tetrahedron, 48, 9735-9735 (1992)
Fangrui Wu et al.
Journal of the American Chemical Society, 134(3), 1498-1500 (2012-01-11)
The Pictet-Spenglerase strictosidine synthase (STR1) has been recognized as a key enzyme in the biosynthesis of some 2000 indole alkaloids in plants, some with high therapeutic value. In this study, a novel function of STR1 has been detected which allows
Kaushik Chanda et al.
Molecular diversity, 15(2), 569-581 (2010-10-12)
The Pictet-Spengler reaction, using polyethylene glycol immobilized tryptophan ester with a variety of ketones, was achieved by refluxing condition in acidic chloroform. The linear as well as cyclic ketones were employed. All the ketones were reacted within 6-8 h to
I M McDonald et al.
Journal of medicinal chemistry, 43(19), 3518-3529 (2000-09-23)
A novel series of nonpeptide CCK(2) receptor antagonists has been prepared, in which 2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1, 4]diazonine (5) was used as a chemical template. This uncommon ring system was obtained in a highly substituted form and in high yield by ozonolysis of
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