82156-58-9Relevant academic research and scientific papers
Asymmetric Organocatalytic Synthesis of Bisindoles – Scope and Derivatizations
Retich, Christina,Br?se, Stefan
supporting information, p. 60 - 77 (2018/01/17)
Starting from 3-vinylindoles and glyoxolate imines, we created a library of diverse 4,6-bis(1H-indole-3-yl)piperidine 2-carboxylates by using 10 mol-% of a chiral phosphoric acid. Utilising electron-withdrawing groups on the starting material during the r
Synthesis and antidepressant-like activity of novel aralkyl piperazine derivatives targeting SSRI/5-HT1A/5-HT7
Gu, Zheng-Song,Zhou, Ai-nan,Xiao, Ying,Zhang, Qing-Wei,Li, Jian-Qi
, p. 701 - 715 (2018/01/03)
A series of novel aralkyl piperazine derivatives were synthesized, and evaluated for their serotonin reuptake inhibitory and 5-HT1A/5-HT7 receptors affinities activity. Antidepressant activities in vivo of the compounds were screened using the forced swimming test (FST) and tail suspension test (TST). The results indicated that compounds 21k (RUI, IC50 = 31 nM; 5-HT1A, 5-HT7, ki = 62, 12 nM) and 21n (RUI, IC50 = 25 nM; 5-HT1A, 5-HT7, ki = 28, 3.3 nM) exhibited high affinities for the 5-HT1A/5-HT7 receptors coupled with potent serotonin reuptake inhibition. Specifically, the most promising compound 21n possessed a good oral pharmacokinetic properties and an acceptable hERG profile, and showed potent antidepressant-like effect in the FST and TST models.
PLANT GROWTH REGULATOR COMPOUNDS
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Page/Page column 29; 31, (2018/04/13)
The present invention relates to relates to novel strigolactone derivatives of formula (I), to processes for preparing these derivatives including intermediate compounds, to seeds comprising these derivatives, to plant growth regulator or seed germination promoting compositions comprising these derivatives and to methods of using these derivatives in controlling the growth of plants and/or promoting the germination of seeds.
Efficient Difluoromethylation of Alcohols Using TMSCF2Br as a Unique and Practical Difluorocarbene Reagent under Mild Conditions
Xie, Qiqiang,Ni, Chuanfa,Zhang, Rongyi,Li, Lingchun,Rong, Jian,Hu, Jinbo
supporting information, p. 3206 - 3210 (2017/03/17)
A general method for the efficient difluoromethylation of alcohols using commercially available TMSCF2Br (TMS=trimethylsilyl) as a unique and practical difluorocarbene source is developed. This method allows primary, secondary, and even tertiary alkyl difluoromethyl ethers to be synthesized under weakly basic or acidic conditions. The reaction mainly proceeds through the direct interaction between a neutral alcohol and difluorocarbene, which is different from the difluoromethylation of phenols. Moreover, alcohols containing other moieties that are also reactive toward difluorocarbene can be transformed divergently by using TMSCF2Br. This research not only solves the synthetic problem of difluorocarbene-mediated difluoromethylation of alcohols, it also provides new insights into the different reaction mechanisms of alcohol difluoromethylation and phenol difluoromethylation with difluorocarbene species.
OPIOID RECEPTOR MODULATORS
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Page/Page column 97; 98, (2016/06/14)
The present invention provides a compound having the structure wherein A is a ring structure, with or without substitution; X1 is C or N; X2 is N, 0, or S; Y1 is H, -(alkyi), -(alkenyl), -(alkynyl), -(cycloalkyi), (haloalkyi), -(alkyl)-O-(alkyl) or -(alky
Constructing iboga alkaloids via C-H bond functionalization: Examination of the direct and catalytic union of heteroarenes and isoquinuclidine alkenes
Kruegel, Andrew C.,Rakshit, Souvik,Li, Xiaoguang,Sames, Dalibor
, p. 2062 - 2071 (2015/10/12)
The iboga alkaloids have attracted considerable attention in both the scientific community and popular media due to their reported ability to reverse or markedly diminish cravings for, and self-administration of, the major drugs of abuse. We have developed three new intramolecular C-H functionalization procedures leading to the core seven-membered ring of the iboga skeleton, a cyclization that proved to be highly challenging. The electrophilic palladium salt Pd(CH3CN)4(BF4)2 was effective for the cyclization of diverse N-(2-arylethyl)isoquinuclidines with yields of 10-35%. A two-step, bromination-reductive Heck reaction protocol was also effective for the synthesis of ibogamine in 42% yield. Finally, a direct Ni(0)-catalyzed C-H functionalization provided the benzofuran analogues of ibogamine (74%) and epi-ibogamine (38%). Although each approach suffers from significant shortcomings, in combination, the methods described provide practical routes to diverse ibogamine analogues.
SMALL MOLECULE INDUCERS OF GDNF AS POTENTIAL NEW THERAPEUTICS FOR NEUROPSYCHIATRIC DISORDERS
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Page/Page column 101; 102, (2013/03/26)
The invention provides a compound having the structure (I), wherein A is a substituted or unsubstituted ring; Z is present or absent and when present is (II), wherein n is 0, 1, 2, 3, or 4; Y is -(CR11R12)-, -NH(CR11R12)- or -O(CR11R12)- wherein R11 and R12 are each hydrogen or combine to form a carbonyl; and wherein R1 to R10 are herein as described.
Novel benzofuran derivatives with dual 5-HT1A receptor and serotonin transporter affinity
Venkatesan, Aranapakam M.,Dos Santos,Ellingboe, John,Evrard, Deborah A.,Harrison, Boyd L.,Smith, Deborah L.,Scerni, Rosemary,Hornby, Geoffrey A.,Schechter, Lee E.,Andree, Terrence H.
scheme or table, p. 824 - 827 (2010/06/13)
Several benzofuran derivatives linked to a 3-indoletetrahydropyridine through an alkyl chain were prepared and evaluated for serotonin transporter and 5-HT1A receptor affinities. Their design, synthesis and structure-activity relationships are described.
BENZOFURANYL- AND BENZOTHIENYL- PIPERAZINYL QUINOLINES AND METHODS OF THEIR USE
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Page/Page column 21, (2009/04/24)
Benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and/or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.
From a natural product lead to the identification of potent and selective benzofuran-3-yl-(indol-3-yl)maleimides as glycogen synthase kinase 3βinhibitors that suppress proliferation and survival of pancreatic cancer cells
Gaisina, Irina N.,Gallier, Franck,Ougolkov, Andrei V.,Kim, Ki H.,Kurome, Toru,Guo, Songpo,Holzle, Denise,Luchini, Doris N.,Blond, Sylvie Y.,Billadeau, Daniel D.,Kozikowski, Alan P.
experimental part, p. 1853 - 1863 (2009/12/31)
Recent studies have demonstrated that glycogen synthase kinase 3β (GSK-3β) is overexpressed in human colon and pancreatic carcinomas, contributing to cancer cell proliferation and survival. Here, we report the design, synthesis, and biological evaluation of benzofuran-3-yl-(indol-3-yl) maleimides, potent GSK-3β inhibitors. Some of these compounds show picomolar inhibitory activity toward GSK-3β and an enhanced selectivity against cyclin-dependent kinase 2 (CDK-2). Selected GSK-3β inhibitors were tested in the pancreatic cancer cell lines MiaPaCa-2, BXPC-3, and HupT3. We determined that some of these compounds, namely compounds 5, 6, 11, 20, and 26, demonstrate antiproliferative activity against some or all of the pancreatic cancer cells at low micromolar to nanomolar concentrations. We found that the treatment of pancreatic cancer cells with GSK-3β inhibitors 5 and 26 resulted in suppression of GSK-3β activity and a distinct decrease of the X-linked inhibitor of apoptosis (XIAP) expression, leading to significant apoptosis. The present data suggest a possible role for GSK-3β inhibitors in cancer therapy, in addition to their more prominent applications in CNS disorders.
