3449-49-8Relevant academic research and scientific papers
Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles
Bi, Hong-Yan,Li, Cheng-Jing,Liang, Cui,Mo, Dong-Liang,Wei, Cui
, p. 5815 - 5821 (2020/09/21)
We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.
THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION
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Page/Page column 89; 90, (2019/01/17)
Disclosed herein are compounds of formula I: or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an anim
Design, synthesis and evaluation of hybrid of tetrahydrocarbazole with 2,4-diaminopyrimidine scaffold as antibacterial agents
Su, Liqiang,Li, Jiahui,Zhou, Zhen,Huang, Dongxia,Zhang, Yuanjin,Pei, Haixiang,Guo, Weikai,Wu, Haigang,Wang, Xin,Liu, Mingyao,Yang, Cai-Guang,Chen, Yihua
, p. 203 - 211 (2018/11/23)
Several 6-substituted tetrahydrocarbazole derivatives were designed, synthesized and evaluated for the antibacterial activities against Staphylococcus aureus Newman strain. Subsequently, 2,4-diaminopyrimidine scaffold was merged with the tetrahydrocarbazole unit to generate a series of novel hybrid derivatives and the antibacterial activities were also investigated. Among these novel hybrids, compound 12c showed the most potent activity with a MIC of 0.39–0.78 μg/mL against S. aureus Newman and Escherichia coli AB1157 strain. In addition, compound 12c exhibited low MIC values against a panel of multidrug-resistant strains of S. aureus.
First-generation structure-activity relationship studies of 2,3,4,9-tetrahydro-1H-carbazol-1-amines as CpxA phosphatase inhibitors
Li, Yangxiong,Gardner, Jessi J.,Fortney, Katherine R.,Leus, Inga V.,Bonifay, Vincent,Zgurskaya, Helen I.,Pletnev, Alexandre A.,Zhang, Sheng,Zhang, Zhong-Yin,Gribble, Gordon W.,Spinola, Stanley M.,Duerfeldt, Adam S.
supporting information, p. 1836 - 1841 (2019/05/22)
Genetic activation of the bacterial two-component signal transduction system, CpxRA, abolishes the virulence of a number of pathogens in human and murine infection models. Recently, 2,3,4,9-tetrahydro-1H-carbazol-1-amines were shown to activate the CpxRA
Synthesis and Oxidative Cleavage of Oxazinocarbazoles: Atropselective Access to Medium-Sized Rings
Liu, Gu,Lancefield, Christopher S.,Lorion, Magali M.,Slawin, Alexandra M. Z.,Westwood, Nicholas J.
supporting information, p. 2808 - 2814 (2015/02/19)
Polycyclic systems can be converted into medium-sized-ring-containing compounds through the controlled oxidative cleavage of internal double bonds. This approach is particularly accessible in systems that contain a suitably substituted indole ring. Here, a robust approach to the synthesis of the understudied oxazinocarbazole system is reported. After regioselective incorporation of a carbonyl functional group, m-chloroperoxybenzoic acid (MCPBA) is used to cleave the indole 2,3-double bond that this system contains. This results in a competition between two processes, oxidative cleavage of the double bond and a pinacol-type rearrangement, both of which occur with very high diastereoselectivity. The balance between the two processes is studied as a function of the substrate structure. Extensive use of X-ray crystallographic analysis of the products enables detailed mechanistic conclusions to be drawn.
A novel necroptosis inhibitor - Necrostatin-21 and its SAR study
Wu, Zhijie,Li, Ying,Cai, Yu,Yuan, Junying,Yuan, Chengye
supporting information, p. 4903 - 4906 (2013/09/02)
An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM.
Montmorillonite-KSF induced Fischer indole cyclization under microwave towards a facile entry to 1-keto-1,2,3,4-tetrahydrocarbazoles
Chakraborty, Suchandra,Chattopadhyay, Gautam,Saha, Chandan
experimental part, p. 201 - 206 (2011/03/22)
Fischer indole cyclization of substituted cyclohexane-1,2-dione-1- phenylhydrazones 1 having either electron donating or electron withdrawing group on the phenyl moiety of substituted 1-keto-1,2,3,4-tetrahydrocarbazoles 2 are efficiently carried out by microwave irradiation in presence of montmorillonite-KSF under solvent free condition.
Substituted tetrahydrocarbazoles with potent activity against human papillomaviruses
Gudmundsson, Kristjan S.,Sebahar, Paul R.,Richardson, Leah D'Aurora,Catalano, John G.,Boggs, Sharon D.,Spaltenstein, Andrew,Sethna, Phiroze B.,Brown, Kevin W.,Harvey, Robert,Romines, Karen R.
scheme or table, p. 3489 - 3492 (2010/03/31)
The synthesis and SAR of a series of substituted 1-aminotetrahydrocarbazoles with potent activity against human papillomaviruses are described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole are outlined and resulting changes in antiviral activity are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the low nanomolar range were identified and (1R)-6-bromo-N-[(1R)-1-phenylethyl]-2,3,4,9-tetrahydro-1H-carbazole-1-amine was selected for further evaluation.
Convenient and efficient synthesis of 1-oxo-1,2,3,4-tetrahydrocarbazoles via Fischer indole synthesis
Sheng, Rong,Shen, Li,Chen, You-Qin,Hu, Yong-Zhou
experimental part, p. 1120 - 1127 (2009/09/08)
A convenient synthesis of 1-oxo-1,2,3,4-tetra-hydrocarbazoles has been developed by reaction of 2-aminocyclohexanone hydrochlorides with various phenylhydrazine hydrochlorides via Fischer indole synthesis under mild conditions. The method is more satisfac
HCV INHIBITORS
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, (2009/07/03)
The present invention relates to compounds that are useful in the treatment of viruses belonging to Flaviviridae, including flaviviruses, pestiviruses, and hepaciviruses. The invention includes compounds useful for the treatment or prophylaxis of dengue fever, yellow fever, West Nile virus, and HCV.
