- Design, synthesis, and molecular docking of new 5-HT reuptake inhibitors based on modified 1,2-dihydrocyclopenta[b]indol-3(4H)-one scaffold
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Abstract: A new group of serotonin reuptake inhibitors containing 1,2-dihydrocyclopenta[b]indol-3(4H)-one scaffold was synthesized, starting from indole 5-((1H-indol-3-yl)(1,3-dioxane-4,6-diones as a key intermediates. Following three transformations including intramolecular cyclization and formation of imines, a series of new ligand for human serotonin transporter was obtained. The ability of these ligands to inhibit human TS3 serotonin transporter as well as selectivity toward human D3 dopamine receptor and dopamine transporter were tested in silico using docking software. Graphical Abstract: SYNOPSIS?A series of new serotonin reuptake inhibitors containing 1,2-dihydrocyclopenta[b]indol-3(4H)-one scaffold were designed and synthesized. Affinity to human TS3 transporter and D3 receptor were tested in silico.[Figure not available: see fulltext.].
- Szewczyk, Milena,Punda, Pawe?,Janikowska, Karolina,Makowiec, S?awomir
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- Transition-Metal-Promoted Oxidative Cyclization to Give 1,2,4-Trisubstituted Carbazole Scaffolds
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Herein, we describe the synthesis of a 1,2,4-trisubstituted carbazole core from 5-(1 H -indol-3-yl)-3-oxopentanoic acid esters or amides. For oxidative cyclization, we tested two different approaches. First, we used manganese triacetate as a conventional moderate oxidizer to ensure the radical course of the reaction. Second, we examined the use of a more complex oxidizing agent I 2 /Me(OTf) 3. In both cases, formation of a fused-ring carbazole system with a 2-hydroxyl and 1-carboxylic substituent were observed. In connection with the formation of an unexpected reaction intermediate, mechanistic aspects of the process were discussed.
- Makowiec, S?awomir,Ryczkowska, Ma?gorzata,Szewczyk, Milena
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p. 4625 - 4634
(2019/12/11)
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- A combination of green solvent and ultrasonic irradiation promotes the catalyst-free reaction of aldehydes, indoles and Meldrum’s acid
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Abstract: A facile and practical approach for the preparation of 3-indole derivatives was performed by the Yonemitsu condensation of indoles with Meldrum’s acid and aldehydes in a mixture of solvent from glycerol and water under ultrasonic irradiation at
- Lü, Cheng-Wei,Wang, Jia-Jing,Liu, Yan-Hang,Shan, Wen-Juan,Sun, Qi,Shi, Lei
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p. 943 - 949
(2017/02/10)
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- Practical Method for the Preparation of 2,2-Dimethyl-5-{aryl[(hetero)aryl]methyl}-1,3-dioxane-4,6-diones: Synthesis and Mechanistic Study
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An efficient practical synthetic procedure has been developed for the synthesis of 2,2-dimethyl-5-{aryl[(hetero)aryl]methyl}-1,3-dioxane-4,6-diones through Friedel-Crafts alkylation. The scope and limitation of the reaction of 2,2-dimethyl-5-arylidene-1,3
- Najda, Ewelina,Zakaszewska, Anna,Janikowska, Karolina,Makowiec, S?awomir
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p. 3589 - 3596
(2016/10/17)
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- Scandium triflate-catalyzed nucleophilic additions to indolylmethyl Meldrum's acid derivatives via a gramine-type fragmentation: Synthesis of substituted indolemethanes
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Treatment of indolylmethyl Meldrum's acids with catalytic scandium triflate and a variety of nucleophiles results in the nucleophilic displacement of the Meldrum's acid moiety via a gramine-type fragmentation. The reaction is useful for the generation of
- Armstrong, Erin L.,Grover, Huck K.,Kerr, Michael A.
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p. 10534 - 10540
(2013/11/06)
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- 3-AMINO-1-ARYLPROPYL INDOLES AS MONOAMINE REUPTAKE INHIBITOR
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Compounds of formula I: or pharmaceutically acceptable salts thereof, wherein p, Ar, R1, R2, R3, Ra, Rb, Rc, Rd and Re are defined herein, pharmaceutical compositions containing them and methods of using them for the preparation of medicaments for treating depression or anxiety.
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Page/Page column 86-87
(2010/02/15)
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- A convenient synthesis of conformationally constrained β-substituted tryptophans
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A short and general synthesis for the preparation of various conformationally constrained β-substituted tryptophans has been elaborated starting from indole, aldehydes and Meldrum's acid by using trimolecular condensation and Curtius rearrangement mediate
- Nemes, Csaba,Jeannin, Laurent,Sapi, Janos,Laronze, Marie,Seghir, Houria,Augé, Franck,Laronze, Jean-Yves
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p. 5479 - 5492
(2007/10/03)
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- Meldrum's Acid in Organic Synthesis. V. Versatile One-pot Synthesis of Indolepropionic Esters via Simultaneous Condensation of Three Different Carbon Components, Indole, Aldehydes and Meldrum's Acid
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When an acetonitrile solution of Meldrum's acid (1), indole (5), and an aliphatic or aromatic aldehyde (8) in the presence of a small amount of proline (except in the case of acetaldehyde) was allowed to stand at 30 deg C, a simultaneous condensation of t
- Oikawa, Yuji,Hirasawa, Hitoshi,Yonemitsu, Osamu
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p. 3092 - 3096
(2007/10/02)
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