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| | 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE Basic information |
| Product Name: | 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE | | Synonyms: | 1,2,3,4-Tetrahydro-β-carboline;1H-Pyrido[3,4-b]indole,2,3,4,9-tetrahydro-;NORELEAGNINE;TETRAHYDRO-BETA-CARBOLINE;TETRAHYDRONORHARMAN;TETRAHYDRONORHARMANE;AKOS JY2083257;2,3,4,9-TETRAHYDRO-1H-PYRIDO[3,4-B]INDOLE | | CAS: | 16502-01-5 | | MF: | C11H12N2 | | MW: | 172.23 | | EINECS: | | | Product Categories: | Indoles and derivatives;Heterocyclic Compounds;Mutagenesis Research Chemicals;Heterocycles | | Mol File: | 16502-01-5.mol | ![1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE Structure](CAS/GIF/16502-01-5.gif) |
| | 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE Chemical Properties |
| Melting point | 206-208 °C(lit.) | | Boiling point | 351.6±32.0 °C(Predicted) | | density | 1.189±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | 10mg/mL in 1N Ammonium Hydroxide in Methanol, DMSO | | pka | 17.78±0.20(Predicted) | | form | Powder or Crystals | | color | White to slightly yellow | | InChI | 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 | | InChIKey | CFTOTSJVQRFXOF-UHFFFAOYSA-N | | SMILES | N1C2=C(C=CC=C2)C2CCNCC1=2 | | LogP | 1.816 (est) | | CAS DataBase Reference | 16502-01-5(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29339900 |
| | 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE Usage And Synthesis |
| Chemical Properties | Tan Solid | | Uses | 1,2,3,4-Tetrahydro-β-carboline is a mitotic kinesin inhibitor as novel anti-cancer agent. It is used in the study of neurodegenerative diseases. | | Definition | ChEBI: 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole is a member of beta-carbolines. | | 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 | | General Description | Ozonolysis of the enamine bond of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole derivatives was studied. | | Synthesis | 1.5 g of tryptamine was dissolved in a mixed acetic acid/methanol solvent (AcOH/MeOH = 10:1, v/v) and 345 mg of paraformaldehyde was slowly added. The reaction mixture was stirred at 80 °C for 30 min. After completion of the reaction, the progress of the reaction was monitored by TLC. The reaction system was slowly poured into dilute aqueous ammonia solution (NH4OH/H2O = 1:1, v/v, 80 ml) and the pH was adjusted to 10. The organic phases were combined by extracting three times with a solvent mixture of dichloromethane/methanol (CH2Cl2/MeOH = 10:1, v/v). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with dichloromethane/methanol (CH2Cl2/MeOH = 10:1, v/v) as eluent to give 1.6 g of Intermediate A in 98% yield. The product was a light yellow solid, stable at room temperature. | | in vivo | Tetrahydro-β-carboline (20 μg; i.c.v.) increases the serotonin levels in the same part of the brain in rats[1]. | Animal Model: | 180-200g female Sprague-Dawley rats[1] | | Dosage: | 20 μg | | Administration: | Intraventricular injection | | Result: | Increased of serotonin levels in the same part of the brain whereas the monoamine oxidase activity was not altered. |
| | IC 50 | serotonin: 6.1 μM (Ki) | | References | [1] CHRISTIAN O ALBERTO Michiru H Robert B Trask. Dopamine acts as a partial agonist for α2A adrenoceptor in melanin-concentrating hormone neurons.[J]. Journal of Neuroscience, 2011, 31 29: 10671-10676. DOI:10.1523/JNEUROSCI.6245-10.2011.
[2] IAIN M. MCDONALD. 2,7-Dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine as a New Template for the Design of CCK2 Receptor Antagonists[J]. Journal of Medicinal Chemistry, 2000, 43 19: 3518-3529. DOI:10.1021/jm000960w.
[3] Rommelspacher, H., Bade, P., Coper, H., et al. Inhibition of the reuptake of serotonin by tryptoline. Naunyn Schmiedebergs Arch. Pharmacol. 292(1), 93-95 (1976).
[4] Pannier, L., and Rommelspacher, H. Actions of tetrahydronorharmane (tetrahydro-β-carboline) on 5-hydroxytryptamine and dopamine mediated mechanisms. Neuropharmacology 20(1), 1-8 (1981).
[5] Rommelspacher, H., Kauffmann, H., Cohnitz, C.H., et al. Pharmacological properties of tetrahydronorharmane (tryptoline). Naunyn Schmiedebergs Arch. Pharmacol. 298(2), 83-91 (1977). |
| | 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE Preparation Products And Raw materials |
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