15741-71-6Relevant articles and documents
Palladium-catalyzed synthesis of tryptamines and tryptamine homologues: synthesis of psilocin
Hu, Chunmei,Qin, Hua,Cui, Yuxin,Jia, Yanxing
, p. 9075 - 9080 (2009)
A new Pd-catalyzed method for the synthesis of tryptamines is developed, and its applications to the synthesis of Corey's aspidophytine tryptamine 15 and psilocin 20 are also described.
Study on the NBS-induced rearrangement of 2-tert-prenyltryptamines
Adla, Santosh Kumar,Golz, Gregor,Jones, Peter G.,Lindel, Thomas
, p. 2161 - 2170 (2010)
Treatment of 2-tert-prenyltryptamines with N-bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert-prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3-b]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement. Georg Thieme Verlag Stuttgart - New York.
Total synthesis of (±)-trigonoliimine C via oxidative rearrangement of an unsymmetrical bis-tryptamine
Qi, Xiangbing,Bao, Hongli,Tambar, Uttam K.
, p. 10050 - 10053 (2011)
We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2′-bis- tryptamine.
Short Total Synthesis of (±)-Gelliusine e and 2,3′-Bis(indolyl)ethylamines via PTSA-Catalyzed Transindolylation
Chantana, Chayamon,Iawsipo, Panata,Jaratjaroonphong, Jaray,Sirion, Uthaiwan
, p. 13360 - 13370 (2021/10/01)
A first and short total synthesis of the marine sponge 2,3′-bis(indolyl)ethylamine (2,3′-BIEA) alkaloid (±)-gelliusine E was performed in both a three-step divergent approach and a one-pot three-component approach with an overall yield of up to 58%. A key feature of the novel strategy is PTSA-catalyzed transindolylation of the readily synthesized 3,3′-BIEAs with tryptamine derivatives. The structure of the isolated natural product is revised as protonated (±)-gelliusine E (4′). By design, this modular route allows the rapid synthesis of other members of the 2,3′-BIEA family, for example, (±)-6,6′-bis-(debromo)-gelliusine F and analogues with step economy, operational simplicity, and reduced waste. Furthermore, their cytotoxicity in breast cancer cells was investigated.
Inhibitory activity on cholinesterases produced by aryl-phthalimide derivatives: green synthesis, in silico and in vitro evaluation
Andrade-Jorge, Erik,Padilla-Martínez, Itzia I.,Ruiz-Maciel, Omar,Sánchez-Labastida, Luis A.,Soriano-Ursúa, Marvin A.,Trujillo-Ferrara, José G.
, (2020/05/08)
Background: Alzheimer’s disease (AD) is characterized by cognitive impairment and loss of immediate memory resulting from neuronal death in different brain areas, mainly those producing acetylcholine. Acetylcholinesterase inhibitors improve cognitive function, delay mental deterioration, and reduce other symptoms. Despite being the cornerstone for treating mild–moderate AD, these compounds are only palliative agents and often have severe adverse effects. Recently, butyrylcholinesterase (BuChE) has been found to be involved in AD. The aim of this study was to synthesize a series of six phthalimides with structural relationship with monoamines and evaluate them in vitro and in silico as AChE and BuChE inhibitors. In addition, a modified version of the Bonting and Featherstone method for determining AChE activity was adapted for the assessment of BuChE activity. Results: Six molecules (dioxoisoindolines A–F) were synthesized in good yields using a green chemistry approach. Dioxoisoindolines E and F were more active for AChE, with a Ki of 232 and 193 μM, respectively. Contrarily, dioxoisoindolines C and D showed up to fivefold greater selectivity for BuChE than AchE, with a Ki of 200 and 100 μM, respectively. The competitive inhibitory activity of the latter two molecules was similar to that of the reference compounds. Molecular docking demonstrated the participation of carbonyl carbons and aromatic rings in the high affinity of dioxoisoindoles for cholinesterases. Conclusion: The modified version of the Bonting and Featherstone method was successfully adapted to quantify BuChE activity. Dioxoisoindolines C and D displayed greater inhibition of BuChE versus AChE, with good inhibition of both enzymes. Thus, they are promising lead compounds for developing new BuChE/AChE inhibitors. [Figure not available: see fulltext.]
Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Tronocarpine Enabled by an Asymmetric Michael/Aldol Reaction
Han, Fu-She,Liu, Chao-You,Tan, Dong-Xing,Zhou, Jie
supporting information, p. 3834 - 3839 (2020/02/11)
We present the first asymmetric total synthesis and absolute configuration determination of (+)-tronocarpine. The [6.5.7.6.6] pentacyclic core was constructed at an early stage by using a sequential cyclization strategy through a newly developed catalytic asymmetric Michael/aldol cascade to build the aza[3.3.1]-bridged cycle and a tandem reduction/hemiamidation procedure to assemble the seven-membered lactam. The side-chain functionalities were incorporated at a late stage by several appropriately orchestrated manipulations under mild conditions. The synthesis of enantiomerically pure (+)-tronocarpine was achieved through a 20-step longest linear sequence from tryptamine.
Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes
Caramenti, Paola,Nandi, Raj Kumar,Waser, Jerome
supporting information, p. 10049 - 10053 (2018/07/29)
A new method for the synthesis of bi-heteroaryls is reported, based on the umpolung of indoles with benziodoxol(on)e hypervalent iodine reagents (IndoleBX). The oxidative coupling of IndoleBX with an equimolar amount of electron-rich benzenes, indoles, pyrroles, and thiophenes proceeded under mild transition-metal-free conditions. Functionalized non-symmetrical bi-indolyl heterocycles were accessed efficiently. Introduction of a new type of C2-substituted indole benziodoxole reagents further allowed extending the scope of the reaction to NH unprotected and C3-alkylated indoles. The obtained bi-heterocycles are important building blocks in synthetic and medicinal chemistry, and could be easily transformed into more complex heterocyclic systems.
Preparation method of 3-substituted oxidized indole and derivative
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Paragraph 0065; 0067; 0116, (2018/06/26)
The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry and particularly relates to a method of preparing 3-substituted oxidized indole and a derivative. In themethod, with a 3-substituted indole derivative as a raw material and one or more of a tetrabutyl ammonium halide compound/sodium chloride/sodium iodide/potassium iodide as additives, and one or more of dichloromethane/1,2-dichloroethane/tetrahydrofurane/methylbenzene/1,4-dioxane/ethyl acetate/methanol are added as solvents; then one or more of [bis(trifluoroacetoxyl)iodine]benzene/iodosobenzene diacetate are added as oxidants in order to carry out a reaction with reaction temperature being controlled, thus producing the 3-substituted oxidized indole derivative. The method has gentle reaction conditions, simple operations, short reaction time and high yield, and is free of a metal catalyst and is environment-friendly.
Palladium-catalysed direct C-2 methylation of indoles
Tu, Daoquan,Cheng, Xiuzhi,Gao, Yadong,Yang, Panpan,Ding, Yousong,Jiang, Chao
supporting information, p. 7443 - 7446 (2016/08/16)
A direct C-2 methylation reaction of indoles bearing a readily removable N-2-pyrimidyl moiety as a site-specific directing group has been developed with a palladium catalyst. This reaction relied on the use of KF to promote efficient methylation. A moderate to good yield was achieved in a range of indole substrates.
A phthalimidation protocol that follows protein defined parameters
Singudas, Rohith,Adusumalli, Srinivasa Rao,Joshi, Pralhad Namdev,Rai, Vishal
supporting information, p. 473 - 476 (2015/01/09)
This work outlines the first phthalimidation protocol suitable for protein labeling and performed in aqueous media at room temperature and neutral pH with no catalyst or co-reagent required. The methodology is suitable for a range of amines and its efficiency was determined with chemoselective and site-selective protein labeling. This journal is
