50302-61-9

Basic information

• Product Name: trans-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)benzene
• Synonyms: trans-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)benzene
• CAS NO: 50302-61-9
• Molecular Weight: 306.364
• Mol File: 50302-61-9.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: trans-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: trans-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)benzene(50302-61-9)
• EPA Substance Registry System: trans-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)benzene(50302-61-9)

Safety Data

• Hazardous Substances Data: 50302-61-9(Hazardous Substances Data)

Upstream product

• 104331-02-4 N^α-phenylthiocarbonyltryptophan methyl ester 
• 104331-05-7 rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester 
• 100-52-7 benzaldehyde 
• 73327-10-3 N_b-benzyltriptophan methyl ester 
• 123050-52-2 trans-2-benzyl-3-(methoxycarbonyl)-1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 7303-49-3 DL-tryptophan methyl ester 
• 104330-92-9 3-methoxycarbonyl-1-phenyl-3,4-dihydro-9H-pyrido<3,4-b>indole hydriodide 
• 132337-19-0 methyl 2-nitroso-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 
• 19779-75-0 N_b-Benzylidenetryptophan methyl ester 
• 54-12-6 Trp 
• 5619-09-0 methyl tryptophanate hydrochloride 
• 4299-70-1 L-tryptophan methyl ester 
• 177217-34-4 2-(benzylidene-amino)-3-(1H-indol-3-yl)-propionic acid methyl ester 

Downstream Products

• 50302-62-0 2-acetyl-1t-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3r-carboxylic acid methyl ester 
• 113247-41-9 Methyl 2-acetylamino-3-(2-benzoylindol-3-yl)propionate 
• 113247-44-2 Methyl 3-(1-acetyl-2-benzoylindol-3-yl)-2-diacetylaminopropionate 
• 1262842-25-0 C₂₆H₂₄N₂O₄S 
• 374708-73-3 1-phenyl-β-carboline-3-carboxylic acid hydrazide 

Relevant articles and documents

β-Carboline tethered cinnamoyl 2-aminobenzamides as class I selective HDAC inhibitors: Design, synthesis, biological activities and modelling studies

The effect of β-carboline motif as cap for HDAC inhibitors containing cinnamic acid as linker and benzamides as zinc binding group was examined in this study. A series of β-carboline-cinnamide conjugates have been synthesized and evaluated for their HDAC inhibitory activity and in vitro cytotoxicity against different human cancer cell lines. Almost all the compounds exhibited superior HDAC inhibitory activity than the standard drug Entinostat for in vitro enzymatic assay. Among the tested compounds, 7h displayed a noteworthy potency with an IC50 value of 0.70 ± 0.15 μM against HCT-15 cell line when compared to the standard drug Entinostat (IC50 of 3.87 ± 0.62 μM). The traditional apoptosis assays such as nuclear morphological alterations, AO/EB, DAPI, and Annexin-V/PI staining revealed the antiproliferative activity of 7h while depolarization of mitochondrial membrane potential by JC-1 was observed in dose-dependent manner. Cell cycle analysis also unveiled the typical accumulation of cells in G2M phase and sub-G1/S phase arrest. In addition, immunoblot analysis for compound 7h on HCT-15 indicated selective inhibition of the protein expression of class I HDAC 2 and 3 isoforms. Molecular docking analysis of compound 7h revealed that it can prominent binding with the active pocket of the HDAC 2. These finding suggest that the compound 7h can be a promising lead candidate for further investigation in the development of novel anti-cancer drug potentially inhibiting HDACs.

Tetrahydro-beta-carboline dimer as well as preparation method and application thereof

The invention discloses an application of a tetrahydro-beta-carboline dimer derivative in the preparation of a medicine for preventing or treating Alzheimer's disease. The tetrahydro-beta-carboline dimer derivative is as shown in a structural formula I, which is described in the specification, L-tryptophan and tryptamine are used as raw materials; a tetrahydro-beta-carboline monomer is generated through a Picet-Spengler reaction and aldehyde cyclization, then a tetrahydro-beta-carboline dimer is generated through acyl chloride connection and a click chemical reaction, the synthesis steps are simple, the raw materials are easy to obtain, the yield is high, and the tetrahydro-beta-carboline dimer has remarkable inhibitory activity on butyrylcholine esterase and A[beta]1-42 aggregation. According to the neural protective effect under three AD models on cells, after the cells are independently treated by A[beta]1-42, H2O2 and OA, the survival rate of the cells is low, and apoptosis or necrosis of the cells occurs. The compounds 11, 12, 13, 17 and 19 are used for co-treatment, the compounds 11, 12, 13, 17 and 19 successfully block A[beta]1-42, H2O2 and OA induced cell death, and it is proved that the compounds 11, 12, 13, 17 and 19 have a remarkable neural protective effect.

Cu-catalyzed mild and efficient oxidation of THβCs using air: Application in practical total syntheses of perlolyrine and flazin

A mild, efficient and environmentally benign method for synthesis of aromatic β-carbolines via Cu(ii)-catalyzed oxidation of 1,2,3,4-tetrahydro-β-carbolines (THβCs) was developed, in which air (O2) was used as the clean oxidant. This method has advantages such as environmentally friendliness, mildness, very good tolerance of functional groups, high yielding and easy experiment operation. In addition, this new methodology was successfully applied in the efficient and practical total syntheses of β-carboline alkaloids perlolyrine and flazin.