60857-68-3Relevant academic research and scientific papers
A six hydrogen pyrrole [2,3-b] process for the preparation of indole derivatives
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, (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.
