19839-52-2Relevant academic research and scientific papers
A facile synthesis of 3-substituted 9H-pyrido[3,4-b]indol- 1(2H)-one derivatives from 3-substituted β-carbolines
Lin, Guowu,Wang, Yue,Zhou, Qingfa,Tang, Weifang,Wang, Jian,Lu, Tao
, p. 5680 - 5691 (2010)
A mild and efficient two-step synthesis of 3-substituted β-carbolinone derivatives from 3-substituted β-carboline in good yields is described. A possible reaction mechanism for the formation of the skeleton of β-carbolin-1-one is proposed. The structures of these compounds were established by IR, 1H-NMR, 13C-NMR, mass spectrometry and elemental analysis, as well as X-ray crystallographic analysis of 4-2 and 6-2.
An expedient stereoselective route to the ACE tricyclic core of manzamine A via a palladium-catalysed arylative allene spirocyclisation cascade
Hawkins, Alison,Jakubec, Pavol,Ironmonger, Alan,Dixon, Darren J.
, p. 365 - 369 (2013)
Application of a novel palladium-catalysed stereoselective arylative allene spirocyclisation cascade as the key step for the construction of the ACE tricyclic core of manzamine A is described.
Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals
Shen, Tao,Zhu, Bencong,Lin, Fengguirong,Pan, Jun,Wei, Jialiang,Luo, Xiao,Liu, Jianzhong,Jiao, Ning
, p. 815 - 818 (2018/07/31)
A direct and structurally divergent synthesis of indole alkaloids from very simple 2-vinylanilines, alkynes and TBN via a novel substrate fragmentation/cycloaddition strategy has been developed, which provides an efficient noble-metal-free approach to access a library of highly valuable indole derivatives of tryptamines and tryptamine-related oximes, lactams, and lactones, as well as β-carbolines, spiroindolines, and hexa-hydropyrrolo[2,3-b]indoles.
Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C - C Triple Bond Cleavage and Dioxygen Activation
Shen, Tao,Zhang, Yiqun,Liang, Yu-Feng,Jiao, Ning
, p. 13147 - 13150 (2016/10/24)
An unexpected metal-free C - C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.
Efficient synthesis of eudistomin U and evaluation of its cytotoxicity
Roggero, Chad M.,Giulietti, Jennifer M.,Mulcahy, Seann P.
supporting information, p. 3549 - 3551 (2014/07/22)
Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as β-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis
Efficient synthesis of eudistomin U and evaluation of its cytotoxicity
Roggero, Chad M.,Giulietti, Jennifer M.,Mulcahy, Seann P.
supporting information, p. 3549 - 3551 (2015/02/19)
Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as β-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis
A new, simple, and high-yielding synthesis of 2,9-Dihydro-1 H- pyrido[3,4- b ]indol-1-ones
La Regina, Giuseppe,Famiglini, Valeria,Passacantilli, Sara,Pelliccia, Sveva,Punzi, Pasqualina,Silvestri, Romano
, p. 2093 - 2097 (2014/08/05)
A new, simple, and high-yielding method was developed to prepare 2,9-dihydro-1H-pyrido[3,4-b]indol-1-ones by selective cyclization of the appropriate N-(2,2-dimethoxyethyl)-1H-indole-2-carboxamide in polyphosphoric acid at 110 °C for 30 minutes. The reaction yield was strongly dependent on the acid used. The method was less affected by the presence of electron-donating and -withdrawing substituents at 5-position of the indole nucleus. Georg Thieme Verlag Stuttgart, New York.
Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines
Ma, Chunming,Cao, Rihui,Shi, Buxi,Zhou, Xiantai,Ma, Qin,Sun, Jie,Guo, Liang,Yi, Wei,Chen, Zhiyong,Song, Huacan
scheme or table, p. 5513 - 5519 (2010/12/20)
The condensation of alkylenediamine with ethyl β-carboline-1- carboxylate and 1-bromo-β-carboline gave β-carboline-1-carboxamides and 1-amino-β-carbolines, respectively. Some of these β-carbolines were active against a panel of human tumor cell lines, and 1-amino derivatives were more potent than their 1-carboxamide congeners. In particular, among the 1-amino-β-carbolines, the N9-arylated alkyl substituted β-carbolines exhibited the most interesting cytotoxic activities with IC50 value of lower than 20 μM. The preliminary structure-activity relationships (SARs) analysis suggested that (1) 1-amino substituents were the advisable pharmacophoric group for enhanced cytotoxic activities; (2) the introduction of appropriate arylated alkyl groups into position-9 of β-carboline facilitated their cytotoxic potencies.
Synthesis of α-carbolines and β-carbolinones via intramolecular Diels- Alder reactions of 2(1H)-pyrazinones
Tahri, Abdellah,Buysens, Kris J.,Van Der Eycken, Erik V.,Vandenberghe, Didier M.,Hoornaert, Georges J.
, p. 13211 - 13226 (2007/10/03)
2(1H)-Pyrazinones bearing a X-(o-C6H4)-C≡C-R moiety (X=NH, NAc) are shown to undergo an intramolecular cycloaddition-elimination reaction on thermolysis in refluxing bromobenzene yielding α-carbolines or β- carbolinones. The product distribution depends strongly on the substitution pattern of the pyrazinone precursors and the solvent used for thermolysis. A high yield and selective formation of β-carbolinones is possible when heating in tetrahydronaphthalene at reflux. Use of acetic anhydride as solvent facilitated the reaction and made it possible to realise a carbolin(on)e unaccessible by thermolysis in the previously mentioned solvents.
β-Carboline Alkaloids, I. - Syntheses of 1-Aryl and 1-Alkenyl-β-carbolines by Palladium-Catalyzed Coupling Reactions
Bracher, Franz,Hildebrand, Dirk
, p. 1315 - 1320 (2007/10/02)
1-Chloro-β-carboline (6) is prepared in three steps starting from tryptamine (3).Palladium-catalyzed coupling reactions of 6 with aryl boronic acids offer an easy access to the alkaloids komaroine (11) and perlolyrine (15).Pavettine (16) is prepared by co
