91200-21-4

Basic information

• Product Name: (1S,3S)-methyl 1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate
• Synonyms: (1S,3S)-methyl 1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate
• CAS NO: 91200-21-4
• Molecular Weight: 306.364
• Mol File: 91200-21-4.mol
• Article Data: 33

Chemical Properties

• CAS DataBase Reference: (1S,3S)-methyl 1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S)-methyl 1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate(91200-21-4)
• EPA Substance Registry System: (1S,3S)-methyl 1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate(91200-21-4)

Safety Data

• Hazardous Substances Data: 91200-21-4(Hazardous Substances Data)

Upstream product

• 177217-34-4 2-(benzylidene-amino)-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 5619-09-0 methyl tryptophanate hydrochloride 
• 100-52-7 benzaldehyde 
• 31771-33-2 2-phenyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine 
• 4299-70-1 L-tryptophan methyl ester 
• 67-56-1 methanol 
• 209169-30-2 (3S)-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 
• 73-22-3 L-Tryptophan 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 93598-41-5 cis-1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester hydrochloride 
• 6159-33-7 L-tryptophan hydrochloride 
• 131614-18-1 (1S,3S)-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid 
• 85239-37-8 (S)-3-(1H-Indol-3-yl)-2-thiobenzoylamino-propionic acid methyl ester 
• 2717-75-1 N-benzoyl-L-tryptophan methyl ester 

Downstream Products

• 111596-22-6 cis-2-benzyl-3-(methoxycarbonyl)-1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b> indole 
• 274677-77-9 2-[1-(9H-fluoren-9-ylmethoxycarbonyl)-pyrrolidine-2-carbonyl]-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 1224845-19-5 (6S,12aR)-2-benzyl-2,3,6,7,12,12a-hexahydro-6-phenyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione 
• 1224845-00-4 Trans-2,3,6,7,12,12a-hexahydro-2-benzyl-6-phenyl-pyrazino[2',1';6,1]pyrido[3,4-b]indole-1,4-dione 
• 1262842-25-0 C₂₆H₂₄N₂O₄S 
• 374708-73-3 1-phenyl-β-carboline-3-carboxylic acid hydrazide 
• 179799-40-7 C₁₈H₁₇N₃O 
• 131614-18-1 (1S,3S)-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid 

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.

Discovery and preliminary mechanism of 1-carbamoyl β-carbolines as new antifungal candidates

Natural β-carboline alkaloids are ideal models for the discovery of pharmaceutically important entities. Various 1-substituted β-carbolines were synthesized from commercially inexpensive tryptophan and demonstrated significant in vitro antifungal activity against G. graminis. Significantly, compound 4m (EC50 = 0.45 μM) with carboxamide at 1-position displayed the best efficacy and nearly 20 folds enhancement in antifungal potential compared to Silthiopham (EC50 = 8.95 μM). Moreover, compounds 6, 7, and 4i exhibited excellent in vitro antifungal activities and in vivo protective and curative activities against B. cinerea and F. graminearum. Preliminary mechanism studies revealed that compound 4m caused reactive oxygen species accumulation, cell membrane destruction, and deregulation of histone acetylation. These findings indicated that 1-carbamoyl β-carboline can be selected as a promising model for the discovery of novel and broad-spectrum fungicide candidates.

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.