40619-69-0Relevant academic research and scientific papers
Total synthesis of (±)-psychotrimine
Newhouse, Timothy,Baran, Phil S.
, p. 10886 - 10887 (2008)
A new process for the union of anilines with tryptamine derivatives has been developed, furnishing C-3 quaternized pyrroloindoline architectures. This chemoselective coupling of a tryptamine with 1.2 equiv of 2-iodoaniline proceeds efficiently on a gram-scale using only the simple reagents N-iodosuccinimide and triethylamine. Using this new reaction, the complex natural product psychotrimine has been fashioned with a rare level of efficiency and practicality. From a readily available bromotryptamine, only four steps (41-45% overall isolated yield) are necessary to procure gram quantities of the natural product. Functional group manipulations, protecting group chemistry, and unnecessary redox fluctuations have been minimized. Copyright
N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential
Bojarski, Andrzej J.,Bugno, Ryszard,Cie?lik, Paulina,Duszyńska, Beata,Handzlik, Jadwiga,Hogendorf, Adam S.,Hogendorf, Agata,Kaczorowska, Katarzyna,Kurczab, Rafa?,Latacz, Gniewomir,Lenda, Tomasz,Sata?a, Grzegorz,Staroń, Jakub,Szewczyk, Bernadeta
, (2021/08/17)
A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.
Facile in Vitro Biocatalytic Production of Diverse Tryptamines
McDonald, Allwin D.,Perkins, Lydia J.,Buller, Andrew R.
, p. 1939 - 1944 (2019/07/08)
Tryptamines are a medicinally important class of small molecules that serve as precursors to more complex, clinically used indole alkaloid natural products. Typically, tryptamine analogues are prepared from indoles through multistep synthetic routes. In the natural world, the desirable tryptamine synthon is produced in a single step by l-tryptophan decarboxylases (TDCs). However, no TDCs are known to combine high activity and substrate promiscuity, which might enable a practical biocatalytic route to tryptamine analogues. We have now identified the TDC from Ruminococcus gnavus as the first highly active and promiscuous member of this enzyme family. RgnTDC performs up to 96 000 turnovers and readily accommodates tryptophan analogues with substituents at the 4, 5, 6, and 7 positions, as well as alternative heterocycles, thus enabling the facile biocatalytic synthesis of >20 tryptamine analogues. We demonstrate the utility of this enzyme in a two-step biocatalytic sequence with an engineered tryptophan synthase to afford an efficient, cost-effective route to tryptamines from commercially available indole starting materials.
Preparation method of 7-bromoindole derivative
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Paragraph 0025; 0026, (2017/11/04)
The invention discloses a preparation method of a 7-bromoindole derivative, namely tert-butyl 2-(7-bromo-1H-indol-3-yl)ethylcarbamate. According to the preparation method, 7-bromoindole is taken as a starting raw material, and the target product is obtained by carrying out a friedel-crafts reaction, amidation, reduction and a Boc protection reaction. The compound is an important medical intermediate.
A 1 - (phenyl) - 2, 3, 4, 9-tetrahydro -1H-pyrido [3,4-b] indole derivatives thereof in the preparation of the application of the anti-tumor drug (by machine translation)
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Paragraph 0083-0085, (2016/11/14)
The invention belongs to the technical field of pharmaceutical chemistry, in particular to a kind of 1 - (phenyl) - 2, 3, 4, 9-tetrahydro -1H-pyrido [3,4-b] indole derivatives thereof in the preparation of the application of the anti-tumor drugs. Research display inhibit one or more prostandin receptor activity can be effective for the treatment of hypertension, at least one kind of prostagladin E2 receptor in the blood pressure regulating system RAAS in the course of play a crucial role, we by changing 1 and 8 is the angle of the two groups and the distance to EP3 receptor research, we developed a new high-efficiency of the synthetic route to study a series of derivatives, all of the target compound are all new product, all of the compound through the nuclear magnetic resonance and quality of the identification of the structure. The target compound in the antibacterial, anti-tumor, analgesic, anti-platelet aggregation, the promotion of kidney part of the reabsorption of sodium and water, regulating neurotransmitter release, promote adipose tissue Lipolysis and has an important role of anti-arrhythmia. (by machine translation)
Marine AChE inhibitors isolated from Geodia barretti: Natural compounds and their synthetic analogs
Olsen, Elisabeth K.,Hansen, Espen,Moodie, Lindon W. K.,Isaksson, Johan,Sep?i?, Kristina,Cergolj, Marija,Svenson, Johan,Andersen, Jeanette H.
, p. 1629 - 1640 (2016/02/09)
Barettin, 8,9-dihydrobarettin, bromoconicamin and a novel brominated marine indole were isolated from the boreal sponge Geodia barretti collected off the Norwegian coast. The compounds were evaluated as inhibitors of electric eel acetylcholinesterase. Barettin and 8,9-dihydrobarettin displayed significant inhibition of the enzyme, with inhibition constants (Ki) of 29 and 19 μM respectively towards acetylcholinesterase via a reversible noncompetitive mechanism. These activities are comparable to those of several other natural acetylcholinesterase inhibitors of marine origin. Bromoconicamin was less potent against acetylcholinesterase, and the novel compound was inactive. Based on the inhibitory activity, a library of 22 simplified synthetic analogs was designed and prepared to probe the role of the brominated indole, common to all the isolated compounds. From the structure-activity investigation it was shown that the brominated indole motif is not sufficient to generate a high acetylcholinesterase inhibitory activity, even when combined with natural cationic ligands for the acetylcholinesterase active site. The four natural compounds were also analysed for their butyrylcholinesterase inhibitory activity in addition and shown to display comparable activities. The study illustrates how both barettin and 8,9-dihydrobarettin display additional bioactivities which may help to explain their biological role in the producing organism. The findings also provide new insights into the structure-activity relationship of both natural and synthetic acetylcholinesterase inhibitors.
Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade
Gregory, Alex W.,Jakubec, Pavol,Turner, Paul,Dixon, Darren J.
supporting information, p. 4330 - 4333 (2013/09/24)
A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization proc
8-SUBSTITUTED TETRAHYDRO-BETA-CARBOLINES
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, (2008/06/13)
The present invention provides novel tetrahydro-beta-carboline compounds and intermediates having useful central nervous system activity. The invention provides formulations and methods for using the tetrahydro-beta-carboline and related intermediate compounds. Finally, the invention provides an article of manufacture.
INTERMEDIATES TO TETRAHYDRO-BETA-CARBOLINES
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, (2008/06/13)
3-Ethanamine and 3-ethanamine related compounds are provided that are useful intermediates and have beneficial central nervous system activity.
METHOD FOR TREATING 5HT2B RECEPTOR RELATED CONDITIONS
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, (2008/06/13)
The present invention provides methods for binding a 5-HT 2B receptor in mammals using a both known and novel compounds. Further, the invention provides a method for treating or preventing 5-HT 2B related conditions. Finally, the invention provides an article of manufacture.
