85181-23-3Relevant academic research and scientific papers
5-methoxy-2-methyltryptamine synthesis method
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Paragraph 0018; 0022; 0025, (2020/02/19)
The invention discloses a 5-methoxy-2-methyltryptamine synthesis method, which comprises: synthesizing an intermediate (B) by using 5-methoxyindole-3-formaldehyde (A) and nitroethane as raw materials,and obtaining a target compound 5-methoxy-2-methyltryptamine (C) from the intermediate (B) under the action of a reducing agent lithium aluminum hydride. According to the invention, the method has advantages of mild synthesis conditions, high reaction yield, concise process, cheap and easily available raw materials and simple operation, is suitable for industrial large-scale production, and has wide industrial application prospect and market value.
Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties
Staroń, Jakub,Kurczab, Rafa?,Warszycki, Dawid,Sata?a, Grzegorz,Krawczyk, Martyna,Bugno, Ryszard,Lenda, Tomasz,Popik, Piotr,Hogendorf, Adam S.,Hogendorf, Agata,Dubiel, Krzysztof,Mat?oka, Miko?aj,Moszczyński-P?tkowski, Rafa?,Pieczykolan, Jerzy,Wieczorek, Maciej,Zajdel, Pawe?,Bojarski, Andrzej J.
supporting information, (2019/11/28)
A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (1, 5-HT6R Ki = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R Ki = 25, 5-HT2AR Ki = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with pro-cognitive properties.
Synthesis and structureactivity relationship of novel conformationally restricted analogues of serotonin as 5-HT6 receptor ligands
Nirogi, Ramakrishna V.S.,Kambhampati, Ramasastri,Kothmirkar, Prabhakar,Konda, Jagadishbabu,Bandyala, Thrinath Reddy,Gudla, Parandhama,Arepalli, Sobhanadri,Gangadasari, Narasimhareddy P.,Shinde, Anil K.,Deshpande, Amol D.,Dwarampudi, Adireddy,Chindhe, Anil K.,Dubey, Pramod Kumar
scheme or table, p. 443 - 450 (2012/08/28)
5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structureactivity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the Ki of 23.4 and 20.5nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.
Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
Trujillo, John I.,Meyers, Marvin J.,Anderson, David R.,Hegde, Shridhar,Mahoney, Matthew W.,Vernier, William F.,Buchler, Ingrid P.,Wu, Kun K.,Yang, Syaluan,Hartmann, Susan J.,Reitz, David B.
, p. 4657 - 4663 (2008/02/13)
A structure-activity relationship study was conducted on a series of tetrahydro-β-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNFα production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity.
α-Methyltryptamine sulfonamide derivatives as novel glucocorticoid receptor ligands
Marshall, Daniel R.,Rodriguez, Gus,Thomson, David S.,Nelson, Richard,Capolina, Allison
, p. 315 - 319 (2007/10/03)
α-Methyltryptamine sulfonamides were identified as human glucocorticoid receptor (hGR) ligands in an ultra high throughput screening (UHTS) campaign. Described will be the hit-to-lead activities, including parallel and single point analog synthesis to map the scaffold. Ligands were identified that exhibited 30 nM binding to hGR. The SAR and selectivity of these compounds will be discussed.
