59414-85-6Relevant academic research and scientific papers
Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile
Hock, Katharina J.,Knorrscheidt, Anja,Hommelsheim, Renè,Ho, Junming,Weissenborn, Martin J.,Koenigs, Rene M.
supporting information, p. 3630 - 3634 (2019/02/13)
The functionalization of C?H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C?H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.
A six hydrogen pyrrole [2,3-b] process for the preparation of indole derivatives
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Paragraph 0048, (2016/10/07)
The invention discloses a method for preparing a hexahydropyrrolo [2,3-b] indole derivative. The method comprises the following steps: (1) performing nitrogen hydrocarbylation reaction by taking 3-indole acetonitrile and halogenated hydrocarbon as initial raw materials, dimethyl formamide as a solvent and sodium hydride as an alkaline reagent; (2) adding dimethyl sulfoxide into a middle product obtained in the step (1), and adding glacial acetic acid into a concentrated hydrochloric acid medium to conduct oxidation reaction; (3) subsequently performing substitution reaction on a middle product obtained in the step (2) with halogenated hydrocarbon by taking dimethyl formamide as a solvent and sodium hydride as an alkaline reagent; (4) finally performing reduction closed loop reaction on a middle product obtained in the step (3) in an anhydrous tetrahydrofuran solvent by using lithium aluminum hydride. By adopting the method for preparing the hexahydropyrrolo [2,3-b] indole derivative, the raw materials are cheap and easy to obtain, the reaction is rapid, the operation is convenient, and the yield of the product is high. The crude middle products and the final product prepared by using the method all do not need column chromatography, and the experiment shows that the total yield of the hexahydropyrrolo [2,3-b] indole derivative can reach up to 85%, and the antibacterial activity EC 50 of the hexahydropyrrolo [2,3-b] indole derivative can be up to 4.61 [mu]g/mL.
Synthesis and biological evaluation of hexahydropyrrolo[2,3-b]indole derivatives as fungicides against phytopathogenic fungi
Feng, Jili,Ma, Miaofeng,Li, Ruoxin,Chen, Shu-Wei,Xu, Hui
, p. 892 - 900 (2015/11/17)
Eighteen hexahydropyrrolo[2,3-b]indole derivatives were synthesized and evaluated their in vitro antifungal activities against five phytopathogenic fungal strains through the mycelium growth rate method. Analysis of the structure-Activity relationship on these synthesized compounds revealed that the introduction of benzyl or substituted benzyl group at the C-3a or N-8 position of the pyrroloindoline scaffold conferred higher antifungal activity against all tested phytopathogenic fungi than compound 4a (both C-3a and N-8 positions are prenyl groups). Especially, compound 4r, among all the tested compounds, showed the most effective antifungal activity against Fusarium coeruleum, and Fusarium graminearum with IC50 values of 4.61 and 5.02 μg/mL, respectively. Moreover, all synthesized compounds 4a-4r displayed higher activities against Curvularia lunata than the positive control thiabendazole, a commercial agricultural fungicide.
Synthesis and biological evaluation of (-)- and (+)-debromoflustramine B and its analogues as selective butyrylcholinesterase inhibitors
Rivera-Becerril, Ernesto,Joseph-Nathan, Pedro,Pérez-álvarez, Víctor M.,Morales-Ríos, Martha S.
experimental part, p. 5271 - 5284 (2009/07/01)
A series of pyrrolidinoindolines have been synthesized as debromoflustramine B (4a) analogues for their evaluation as cholinesterase inhibitors. Structure-activity studies of this series revealed the optimum pharmacophore elements required for activity and resulted in the discovery of selective butyrylcholinesterase inhibitors with micromolar potency. Biological testing demonstrated that (-)-4a was 7500 times more potent than its enantiomer (+)-4b. The most active inhibitor against BChE in the series was demethyldebromoflustramine B (5a), with an IC50 value of 0.26 μM. X-ray crystallography of 15 and docking studies of selected compounds into human BChE (PDB 1POI) are presented. Molecular modeling studies showed that π-hydrogen bond, classical hydrogen bond, and cation-π interactions are critical for optimum potency.
Synthesis of new cyclopropanated tryptamine analogues
Szalata, Claude,Sapi, Janos,Szymoniak, Jan,Bertu, Philippes,Gérard, Stéphane
body text, p. 1479 - 1482 (2009/04/07)
A series of tryptamine analogues bearing a cyclopropyl-amine unit was prepared, starting from 3-indolyl acetonitriles, through a MeTi(Oi-Pr) 3-mediated cyclopropanation. Georg Thieme Verlag Stuttgart.
Azepinoindole derivatives as pharmaceutical agents
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, (2008/06/13)
Compounds, compositions and methods for modulating the activity of receptors are provided. In particular, compounds and compositions are provided for modulating the activity of receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder directly or indirectly related to the activity of the receptors.
An efficient method for the N-debenzylation of aromatic heterocycles
Rao, T. Srinivasa,Pandey, Pramod S.
, p. 3121 - 3127 (2007/10/03)
The N-debenzylation of aromatic heterocycles such as substituted pyrroles and indoles, having functional groups like ester, amide, halo, and nitrile, by using sodium in liquid ammonia in the presence of t-BuOH at -78°C cleanly affords N-debenzylated aromatic heterocycles in good yields.
AZEPINOINDOLE AND PYRIDOINDOLE DERIVATIVES AS PHARMACEUTICAL AGENTS
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Page 178, (2008/06/13)
The present invention is directed to compounds of formula (I) and formula (II): formula (I) and (II), wherein R1-R8, A and n are as described in the description. These compounds are used in pharmaceutical compositions and methods for modulating the activity of orphan nuclear receptors.
A CONVENIENT SYNTHESIS OF TRYPTAMINES
Merour, J. Y.,Buzas, A.
, p. 2331 - 2336 (2007/10/02)
Reaction of tosylmethyl isocyanide with substituted formyl indoles gave the nitrile with one more carbon atom.Hydrogenation of this nitrile afforded the corresponding tryptamine.
