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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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Consulter la Bibliothèque de documents

Minoru Tanaka et al.
Bioorganic & medicinal chemistry, 21(5), 1159-1165 (2013-01-23)
Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e
Takayoshi Arai et al.
The Journal of organic chemistry, 76(8), 2909-2912 (2011-03-08)
A four-step synthetic route to fully substituted chiral tetrahydro-β-carbolines (THBCs) is described. Starting from the (R,S,S)-Friedel-Crafts/Henry adduct obtained from three-component coupling of an indole, nitroalkene, and aldehyde catalyzed by imidazoline-aminophenol-CuOTf, the (1S,3S,4R)-THBCs were readily synthesized in a three-step operation including
Fang-Yuan Chang et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(7), 2478-2483 (2013-01-11)
Natural product discovery by random screening of broth extracts derived from cultured bacteria often suffers from high rates of redundant isolation, making it ever more challenging to identify novel biologically interesting natural products. Here we show that homology-based screening of
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
Chem. Abstr., 121, 54854s-54854s (1994)
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