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300764

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

Name: 1,2,3,4-Tetrahydro-9<I>H</I>-pyrido[3,4-<I>b</I>]indole
Brand: ALDRICH

98%

Synonym(s):

Noreleagnine, THBC, Tetrahydronorharman, Tryptoline

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₂N₂

CAS Number:

16502-01-5

Molecular Weight:

172.23

MDL number:

MFCD00004954

UNSPSC Code:

12352100

PubChem Substance ID:

24857939

NACRES:

NA.22

Quality Level

100

Assay

98%

form

liquid

mp

206-208 °C (lit.)

SMILES string

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

InChI key

CFTOTSJVQRFXOF-UHFFFAOYSA-N

Gene Information

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

General description

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

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Triazolyl tryptoline derivatives as β-secretase inhibitors.

Jutamas Jiaranaikulwanitch et al.

Bioorganic & medicinal chemistry letters, 20(22), 6572-6576 (2010-10-15)

Tryptoline, a core structure of ochrolifuanine E, which is a hit compound from virtual screening of the Thai herbal database against BACE1 was used as a scaffold for the design of BACE1 inhibitors. The tryptoline was linked with different side

2,7-Dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine as a new template for the design of CCK(2) receptor antagonists.

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

Discovery of indolotryptoline antiproliferative agents by homology-guided metagenomic screening.

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

Design, synthesis and structure-activity relationship of functionalized tetrahydro-β-carboline derivatives as novel PDE5 inhibitors.

Nermin S Ahmed et al.

Archiv der Pharmazie, 344(3), 149-157 (2011-03-09)

Starting from tadalafil as a template, a series of functionalized tetrahydro-β-carboline derivatives have been prepared and identified as novel potent and selective PDE5 inhibitors. Replacing the 3,4-methylenedioxyphenyl at position 6 of tadalafil, together with elongation of the N2-methyl substituent and

Chem. Abstr., 121, 54854s-54854s (1994)

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