3449-48-7Relevant articles and documents
Novel synthetic method of pirlindole
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Paragraph 0028-0032, (2020/04/17)
The invention belongs to the technical field of medicines, and relates to a synthetic method of pirlindole. According to the method, p-methylphenylhydrazine hydrochloride and 1,2-cyclohexanedione areused as initial raw materials, and conventional methods such as ring closing, condensation, chlorination, alkylation and reduction are carried out to synthesize the pirlindole. The key step of the method comprises ring closing reaction of p-methylphenylhydrazine hydrochloride and 1,2-cyclohexanedione under the action of glacial acetic acid and hydrochloric acid to obtain a key intermediate 6-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-one. The method has the advantages of high yield, cheap and easily available raw materials and lower reaction cost, and is suitable for industrial production.
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.
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 of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation
Shi, Hao,Guo, Tianjian,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 2753 - 2760 (2014/04/17)
A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2- enone with hypervalent iodine reagent PhI(OCOCF3)2 (PIFA), through a direct intramolecular oxidative C(sp2)-C(sp2) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]indol-6(5H)- one skeletons. The mechanism of the process was proposed and briefly discussed.
Sustainable flow oppenauer oxidation of secondary benzylic alcohols with a heterogeneous zirconia catalyst
Chorghade, Rajeev,Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
supporting information, p. 5698 - 5701 (2013/12/04)
A flow chemistry process for the Oppenauer oxidation of benzylic secondary alcohols using partially hydrated zirconium oxide and a simple carbonyl containing oxidant such as acetone, cyclohexanone, and neopentanal is reported. The heterogeneous oxidative system could be applied to a wide range of functionalized alcohol substrates, allowing clean and fast delivery of ketone products within a few minutes between 40 and 100 C.
Regioselective cycloaddition of acetylenic esters: A one-pot synthesis of novel dihydrobenzo[a]carbazoles
Yamuna, Ezhumalai,Zeller, Matthias,Prasad, Karnam Jayarampillai Rajendra
supporting information; experimental part, p. 1649 - 1652 (2011/04/26)
A one-pot procedure for the synthesis of highly substituted dihydrobenzo[a]carbazole derivatives via a regioselective cyclocondensation reaction between 2-(2,3,4,9-tetrahydro-carbazol-1-ylidene)-propanedinitrile and acetylenic esters is described.
Synthesis of 9-substituted 2,3,4,9-tetrahydro-1H-carbazole derivatives and evaluation of their anti-prion activity in TSE-infected cells
Kimura, Tsutomu,Hosokawa-Muto, Junji,Asami, Kenji,Murai, Toshiaki,Kuwata, Kazuo
supporting information; body text, p. 5675 - 5679 (2012/01/02)
2,3,4,9-Tetrahydro-9-[2-hydroxy-3-(1-piperidinyl)propyl] -6-methyl-1H-carbazol-1-one (GJP14) is a novel anti-prion compound that we previously discovered by in silico screening and cellular assay. In this study, a variety of GJP14 derivatives were prepared using pyrrole derivatives, (haloalkyl)oxiranes, and amines, and their anti-prion activity was evaluated in TSE-infected cells. It was found that the tricyclic aromatic ring, a hydroxy group at the 2-position and an amino group at the 3-position of the N-propyl group were the basic requirements for anti-prion activity. The derivatives bearing an N-ortho-halobenzyl group exhibited an improved activity, and the most potent derivative was 8 times as effective as the original lead compound, GJP14.
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.
A novel CAN-SiO2-mediated one-pot oxidation of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoloquinones: Efficient syntheses of murrayaquinone A and koeniginequinone A
Chakraborty, Suchandra,Chattopadhyay, Gautam,Saha, Chandan
body text, p. 331 - 338 (2011/06/19)
One-pot oxidations of substituted 1-keto-1,2,3,4-tetrahydrocarbazoles (1) to carbazole-1,4-quinones (2) are efficiently carried out by CAN-SiO 2-mediated reaction. This generalized protocol was successfully extended to the synthesis of two naturally occurring carbazoloquinones: murrayaquinone A (2b) and koeniginequinone A (2g). A plausible mechanism for this novel reaction involves formation of a 9-hydroxy-2,3,4,9-tetrahydro-1H- carbazole-1-one followed by rearrangement to 1-hydroxycarbazole derivatives, which are further oxidized by cerium (IV) to carbazoloquinones.
