22424-61-9Relevant academic research and scientific papers
The synthesis of alpha, alpha, beta, beta-d4-serotonin.
Shaw,Wright,Milne
, p. 146 - 148 (1976)
Alpha, alpha, beta, beta-d4-Serotonin (94% d4, 6% d3) has been synthesized for use as an internal standard in mass spectrometric determinations of serotonin in biological systems.
Fe-Catalyzed Pictet-Spengler-Type Cyclization via Selective Four-Electron Reductive Functionalization of CO2
Li, Wen-Duo,Chen, Jie,Zhu, Dao-Yong,Xia, Ji-Bao
supporting information, p. 614 - 620 (2021/02/12)
Herein, we describe a novel catalytic Pictet-Spengler-type cyclization using CO2 as a nontoxic and sustainable C1 feedstock with environmentally benign and non-precious-metal iron as catalyst. The reaction is achieved by selective four-electron reduction of CO2 into methylene level intermediate through carefully tuning the reaction parameters. A variety of tetrahydro-β-carbolines and other nitrogen-containing heterocycles can be easily obtained under mild conditions. Mechanistic studies have shown that tetrahydro-β-carbolines are probably obtained via spiroindolenine intermediates.
Design, synthesis, and evaluation of novel anti-trypanosomal compounds
Lepovitz, Lance T.,Martin, Stephen F.,Meis, Alan R.,Mensa-Wilmot, Kojo,Pham, Alexandra,Thomas, Sarah M.,Wiedeman, Justin
supporting information, (2020/03/25)
Human African trypanosomiasis (HAT) is a deadly neglected tropical disease caused by the protozoan parasite Trypanosoma brucei. During the course of screening a collection of diverse nitrogenous heterocycles, we discovered two novel compounds that contain the tetracyclic core of the Yohimbine and Corynanthe alkaloids, were potent inhibitors of T. brucei proliferation and T. brucei methionyl-tRNA synthetase (TbMetRS) activity. Inspired by these key findings, we prepared several novel series of hydroxyalkyl δ-lactam, δ-lactam, and piperidine analogs and tested their anti-trypanosomal activity. A number of inhibitors were more potent against T. brucei than these initial hits with one hydroxyalkyl δ-lactam derivative being 25-fold more effective in our assay. Surprisingly, most of these active compounds failed to inhibit TbMetRS. This work underscores the importance of verifying, irrespective of close structural similarities, that new compounds designed from a lead with a known biological target engage the putative binding site.
Synthesis method of bufotenin and quaternary ammonium salt thereof and application in preparation of analgesic and anti-inflammatory drugs
-
Paragraph 0041-0044; 0061-0064; 0081-0084, (2020/02/29)
The invention relates to a synthesis method of bufotenin and quaternary ammonium salt thereof. The method has the characteristics of simple steps, safe and convenient operation, high reaction efficiency, easy purification and separation, mild conditions a
3-(7-Azaindolyl)-4-indolylmaleimides as a novel class of mutant isocitrate dehydrogenase-1 inhibitors: Design, synthesis, and biological evaluation
Hu, Yuanyuan,Gao, Anhui,Liao, Honghui,Zhang, Mengmeng,Xu, Gaoya,Gao, Lixin,Xu, Lei,Zhou, Yubo,Gao, Jianrong,Ye, Qing,Li, Jia
, (2018/09/06)
A series of 3-(7-azainodyl)-4-indolylmaleimides was designed, synthesized, and evaluated for their isocitrate dehydrogenase 1 (IDH1)/R132H inhibitory activities. Many compounds such as 11a, 11c, 11e, 11g, and 11s exhibited favorable inhibitory effects on IDH1/R132H and were highly selective against the wild-type IDH1. Evaluation of the biological activities at the cellular level showed that compounds 11a, 11c, 11e, 11g, and 11s could effectively suppress the production of 2-hydroxyglutaric acid in U87MG cells expressing IDH1/R132H. Preliminary structure–activity relationship (SAR) and molecular modeling studies were discussed based on the experimental data obtained. These findings may provide new insights into the development of novel IDH1/R132H inhibitors.
A deuterium generation 5- hydroxy primary color ammonia xylosides derivative and its preparation method
-
Paragraph 0040; 0042-0044, (2017/04/11)
The invention discloses deuterated 5-hydroxy tryptophan glucoside derivatives and a preparation method thereof. The preparation method comprises the following steps: first, with 5-benzyloxyindole as an initial material, carrying out acylation reaction and
Towards the development of 5-HT7 ligands combining serotonin-like and arylpiperazine moieties
Spadoni, Gilberto,Bedini, Annalida,Bartolucci, Silvia,Pala, Daniele,Mor, Marco,Riccioni, Teresa,Borsini, Franco,Cabri, Walter,Celona, Diana,Marzi, Mauro,Tarzia, Giorgio,Rivara, Silvia,Minetti, Patrizia
, p. 8 - 35 (2014/05/06)
Many known 5-HT7 ligands contain either a serotonin-like or an arylpiperazine structure that, in published SAR studies, are generally supposed to bind the same receptor pocket. Conversely, we explored the hypothesis that two such moieties can c
Structure-based design leads to the identification of lithium mimetics that block mania-like effects in rodents. Possible new GSK-3β therapies for bipolar disorders
Kozikowski, Alan P.,Gaisina, Irina N.,Yuan, Hongbin,Petukhov, Pavel A.,Blond, Sylvie Y.,Fedolak, Allison,Caldarone, Barbara,McGonigle, Paul
, p. 8328 - 8332 (2008/02/09)
More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3β (GSK-3β) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3β inhibitors. The best ligand in this series (having a Ki value of 4.6 nM against GSK-3β) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3β inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.
Synthesis of a deuterium-labelled standard of bufotenine (5-HO-DMT)
Wang, Yu-Yun,Chen, Chinpiao
, p. 1262 - 1265 (2008/04/12)
The Batcho-Leimgruber strategy was employed to synthesize 3-(2-dimethylamino-[2H4]-ethyl)-1H-indol-5-ol (bufotenine, 5-HO-DMT) (8) from commercial 3-methyl-4-nitro-phenol (1), benzyl bromide and N,N-dimethylformamide-dimethylacetal. Compound 4 was synthesized from compound 3 using the Batcho-Leimgruber strategy in the presence of Raney nickel and hydrazine hydrate. Compound 4 was treated with oxalyl chloride, dimethylamine and lithium aluminum [2H4]-hydride to yield [2-(5-benzyloxy-1H-indol-3-yl)-[2H4]-ethyl] -dimethyl-amine (7). The benzyl ether in compound 7 was cleaved by hydrogenolysis to give bufotenine 8. Copyright
A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and β-carbolines
Wu, Tom Y. H.,Schulte, Peter G.
, p. 4033 - 4035 (2007/10/03)
(matrix presented) Various tryptamines are captured by a vinylsulfonylmethyl polystyrene resin, generating a safety-catch linkage. β-Carbolines can be formed from 4 by a Pictet-Spengler reaction with the introduction of R1. Tryptamine 4 can also be derivatized by acylation or copper-mediated coupling to introduce R2. If X = Br, Suzuki coupling can be used to introduce R3. After derivatization, the indole derivatives are activated with methyl iodide and released under mild basic condition.
