108335-05-3

Basic information

• Product Name: eudistomin T
• Synonyms: eudistomin T;2-Phenyl-1-(9H-pyrido[3,4-b]indol-1-yl)ethanone;Eudistomine T
• CAS NO: 108335-05-3
• Molecular Formula: C₁₉H₁₄N₂O
• Molecular Weight: 286.32726
• Mol File: 108335-05-3.mol

Chemical Properties

• Boiling Point: 530.2°Cat760mmHg
• Flash Point: 268.1°C
• Appearance: /
• Density: 1.293g/cm³
• Vapor Pressure: 2.52E-11mmHg at 25°C
• Refractive Index: 1.736
• CAS DataBase Reference: eudistomin T(CAS DataBase Reference)
• NIST Chemistry Reference: eudistomin T(108335-05-3)
• EPA Substance Registry System: eudistomin T(108335-05-3)

Safety Data

• Hazardous Substances Data: 108335-05-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 3605, 1989 DOI: 10.1016/S0040-4039(01)80460-3

InChI:InChI=1/C19H14N2O/c22-17(12-13-6-2-1-3-7-13)19-18-15(10-11-20-19)14-8-4-5-9-16(14)21-18/h1-11,21H,12H2

Upstream product

• 125305-04-6 1-Phenylacetyl-3,4-dihydro-β-carboline-9-carboxylic acid methyl ester 
• 128690-98-2 3-Oxo-4-phenyl-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid tert-butyl ester 
• 128638-05-1 2,3-Dioxo-4-phenyl-butyric acid tert-butyl ester 
• 103-80-0 phenylacetyl chloride 
• 100571-67-3 2-<3-(1-carbomethoxyindolyl)>ethyl isocyanide 
• 154924-05-7 9H-pyrido[3,4-b]indol-1-yl trifluoromethanesulfonate 
• 19839-52-2 2,9-dihydro-1H-pyrido[3,4-b]indol-1-one 
• 157397-50-7 (+/-)-1-<1'-(tert-butoxycarbonylamino)-2'-phenylethyl>-β-carboline 
• 157397-42-7 (1R,1'S)-1-<1'-(tert-butoxycarbonylamino)-2'-phenylethyl>-1,2,3,4-tetrahydro-β-carboline 
• 72155-45-4 Boc-L-phenylalaninal 
• 61-54-1 tryptamine 
• 169966-68-1 2,2-dimethyl-N-(2-(2-(1-hydroxy-2-phenyl)ethyl-3-fluoro-4-pyridyl)phenyl)propanamide 
• 169966-69-2 1-(4-(2-pivaloylaminophenyl)-3-fluoro-2-pyridyl)-2-phenylethanone 
• 146141-07-3 2,2-dimethyl-N-(2-(3-fluoro-4-pyridyl)phenyl)propanamide 

Relevant articles and documents

Synthesis and characterization of new fluorescent boro-β-carboline dyes

The first representatives of the new fluorescent boro-β-carboline family were synthesized by the insertion of the difluoroboranyl group into the oxaza or diaza core. The resulting compounds showed good photophysical properties with fine Stokes-shifts in the range of 38-85 nm with blue and green emission. The energetics of the excitation states and molecular orbitals of two members were investigated by quantum chemical computations suggesting effects for the improved properties of diazaborinino-carbolines over oxazaborolo-carbolines. These properties nominated this chemotype as a new fluorophore for the development of fluorescent probes. As an example, diazaborinino-carbolines were used for the specific labeling of anti-Her2 antibody trastuzumab. The fluorescent conjugate showed a high fluorophore-antibody ratio and was confirmed as a useful tool for labeling and confocal microscopy imaging of tumour cellsin vitrotogether with theex vivotwo-photon microscopy imaging of tumour slices.

Preparation method of 1-carbonyl-beta-carboline compound

The invention discloses a preparation method of a 1-carbonyl-beta-carboline compound. The preparation method comprises the following step: in an air or oxygen atmosphere, in the presence of an additive and under the condition of illumination, performing oxidation reaction on tetrahydrocarboline compound as shown in a formula II to obtain the 1-carbonyl-beta-carboline compound as shown in a formula I, wherein the additive is tetrabutyl quaternary ammonium salt selected from any one of tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium chloride, tetrabutylammonium acetate and tetrabutylammonium fluoride; and the molar ratio of the tetrahydrocarboline compound as shown in the formula II to the additive is 1:(0.2-2). The preparation method provided by the invention is high in yield, wherein most of the yield is between 60% and 90%. When R3 is an aromatic group, the variety and the position of a substituent group on an aromatic ring do not have substantial influence on the yield of the reaction. In addition, the R3 group has wider applicability and also comprises an alkyl R3 group besides the aromatic R3 group, and in this aspect, the preparation method provided by the invention is substantially improved compared with the existing synthesis.

An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

A facile method for the synthesis of a variety of β-carbolines and their natural products such as norharmane (2a), harmane (2b), eudistomins I, N, T, and U (6, 7, 9 and 10, respectively) has been successfully developed via a decorboxylative aromatization tool by employing N-chlorosuccinimide (NCS) as a mild and efficient reagent. Gratifyingly, this reagent system proceeds in a one-pot manner and converted all the tetrahydro-β-carboline acids into their corresponding decorboxylative aromatic products with good to excellent yields. Additionally, this system works well in the case of tetrahydro-β-carboline esters to produce their aromatic partners in high yields.

Iminophosphorane-mediated synthesis of 1-acyl-β-carbolines : A new access to the alkaloids eudistomin T, S and xestomanzamine A of marine origin

New syntheses of the alkaloids eudistomin T and S are described. The key step, formation of the 1-phenylacetyl β-carboline, involves a tandem aza Wittig/electrocyclic ring closure process. The first synthesis of the alkaloid xestomanzamine A is achieved by coupling of a N-protected harmane, now available via aza Wittig/electrocyclic ring closure process, with a 5-lithioimidazole derivative.

Carbolines, Part VIII. An original synthesis of the antibiotic eudistomin T

An original and short synthesis of Eudistomin T is reported. The approach is based on a convergent methodology which involves such reactions as metalation, heteroring cross-coupling and cyclization.

Diastereoselective Pictet-Spengler Reactions of L-(Boc)Phenylalaninal and L-(Boc)Prolinal: Biomimetic Syntheses of Eudistomin T and (-)-Woodinine

The diastereoselective Pictet-Spengler reaction of L-(Boc)phenylalaninal with tryptamine and the elaboration of this intermediate to the antibacterial compound eudistomin T and analogues of the antileukaemic compound eudistomidin B are described.We also report an efficient synthesis of the naturally occuring alkaloid (-)-woodinine from L-(Boc)prolinal and 5-bromotryptamine in three steps, using a diastereoselective Pictet-Spengler reaction.This approach affords, in addition, formal synthesis of the marine alkaloids eudistomins H and I.

The Chemistry of Vicinal Tricarbonyl Compounds. Short Synthesis of Eudistomins T, I and M

The formation of three novel 1,2,3-tricarbonyl compounds and their use in the total synthesis of eudistomins T, I and M is described.