139655-05-3

Basic information

• Product Name: 1H-Pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-1-(2-nitrophenyl)-
• CAS NO: 139655-05-3
• Molecular Formula: C17H15N3O2
• Molecular Weight: 293.325
• Mol File: 139655-05-3.mol

Chemical Properties

• CAS DataBase Reference: 1H-Pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-1-(2-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-1-(2-nitrophenyl)-(139655-05-3)
• EPA Substance Registry System: 1H-Pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-1-(2-nitrophenyl)-(139655-05-3)

Safety Data

• Hazardous Substances Data: 139655-05-3(Hazardous Substances Data)

Upstream product

• 552-89-6 2-nitro-benzaldehyde 
• 61-54-1 tryptamine 

Downstream Products

• 24243-42-3 1-(2-nitrophenyl)-9H-pyrido[3,4-b]indole 
• 608513-04-8 1-(2-nitrophenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole 
• 1208104-82-8 C₂₄H₂₁N₃O₂ 
• 197177-57-4 1-(2-aminophenyl)-9H-β-carboline 

Relevant articles and documents

Novel polycondensed partly saturated β-carbolines including ferrocene derivatives: Synthesis, DFT-supported structural analysis, mechanism of some diastereoselective transformations and a preliminary study of their in vitro antiproliferative effects

Use of a Pictet-Spengler reaction of tryptamine and L-tryptophan methyl ester and subsequent reduction of the nitro group followed by further cyclocondensation with aryl aldehydes and formyl–substituted carboxylic acids, including ferrocene-based components, furnished a series of diastereomeric 6-aryl-substituted 5,6,8,9,14,14b-hexahydroindolo[2',3':3,4]pyrido[1-c]-quinazolines and 5,5b,17,18-tetrahydroindolo[2',3':3,4]pyrido[1,2-c]isoindolo[2,1-a]quinazolin-11-(15bH)-ones with the elements of central-, planar and conformational chirality. The relative configuration and the conformations of the novel polycyclic indole derivatives were determined by 1H- and 13C-NMR methods supplemented by comparative DFT analysis of the possible diastereomers. The structure of one of the pentacyclic methyl esters with defined absolute configuration “S” was also confirmed by single crystal X-ray diffraction measurement. Accounting for the characteristic substituent-dependent diastereoselective formation of the products multistep mechanisms were proposed on the basis of the results of DFT modeling. Preliminary in vitro cytotoxic assays of the products revealed moderate-to-significant antiproliferative effects against PANC-1-, COLO-205-, A-2058 and EBC-1 cell lines that proved to be highly dependent on the stereostructure and on the substitution pattern of the pending aryl substituent.

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.

Synthesis of tetrahydro-1: H -indolo[2,3- b] pyrrolo[3,2- c] quinolones via intramolecular oxidative ring rearrangement of tetrahydro-β-carbolines and their biological evaluation

A simple oxidative ring rearrangement of diversely substituted 1-(2-amminoaryl)-tetrahydro-β-carbolines has been developed to generate architecturally interesting tetrahydro-1H-indolo[2,3-b]pyrrolo[3,2-c]quinolones. This unique transformation involves fou

Design, synthesis and biological evaluation of a novel library of antimitotic C2-aroyl/arylimino tryptamine derivatives that are also potent inhibitors of indoleamine-2, 3-dioxygenase (IDO)

A novel library of C2-substituted tryptamines (based on diverse C2-aroyl/arylimino indoles and indole-diketopiperazine hybrids) possessing antimitotic properties were designed, synthesized and screened for their inhibitory activity against tubulin polymerization, and against proliferation of A549 lung cancer, HeLa cervical cancer, MCF7 breast cancer and HePG2 liver cancer cell lines. The design of molecules were inspired from known antimitotic compounds and natural products. The molecular docking of the designed compounds indicated that they bind to the colchicin binding site of tubulin. They were synthesized by a unique iodine catalysed oxidative ring opening reaction of 1-aryltetrahydro-β-carbolines. Among the compounds synthesized quite a few compounds induced cytotoxicity on the cancer cells by disrupting the tubulin polymerization. They were found to be non-toxic for healthy cells. Immuno Fluorescence study for the most active molecules (between ~6 μM concentration) against A549 and HeLa cells demonstrated complete disruption and shrinkage of the microtubule structures. These compounds also inhibited indoleamine-2, 3-dioxygenase with low micromolar IC50.

Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives

The synthesis of twelve tetrahydro-β-carboline derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l prepared via the Pictet-Spengler reaction is described. The reaction of tryptamine and a variety of arylaldehydes were carried out under ultrasonic irradiation and trifluoracetic acid catalysis at room temperature. These tetrahydro-β-carbolines have been synthesized in higher yields and shorter reaction times compared to the conventional method. Moreover, the reaction proceeded successfully even employing arylaldehydes with electron-donating or electron-attracting substituents which did not react under conventional method.

Mild and efficient cyanuric chloride catalyzed Pictet-Spengler reaction

A practical, mild and efficient protocol for the Pictet-Spengler reaction catalyzed by cyanuric chloride (trichloro-1,3,5-triazine, TCT) is described. The 6-endo cyclization of tryptophan/tryptamine and modified Pictet-Spengler substrates with both electr

Synthesis of fused polycyclic nitrogen-containing heterocycles via cascade cyclization

A novel strategy for the synthesis of fused polycyclic-nitrogen containing heterocycles via cascade cyclization is described. The methodology involves condensation of 1-(2-aminophenyl)-9H-β-carboline-3-carboxylic acid amide with isothiocyanates followed b

Microwave assisted Pictet-Spengler and Bischler-Napieralski reactions

Pictet-Spengler and Bischler-Napieralski reaction products have been prepared-using microwave irradiation on silicagel support under solvent free condition. Microwave assisted reactions have resulted in better yields of the desired products than prepared

Synthesis of two new heteroaromatic β-carboline-fused pentacycles. Observation of a new intercalating agent

Five-step synthetic routes of two new polyfused heterocycles: indazolo[3,2-a]-β-carboline (3) and benzo[4',5'][1,2,3]triazino[6,1-a]-β-carbolinium salt (10) applying Pd(0)-catalyzed cross-coupling reaction have been elaborated. (C) 2000 Elsevier Science L