- Reactions of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetates. Synthesis of methyl isoxazolo[5,4-a]carbazole-3-carboxylates
-
The reaction of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetates (1a-e) with hydroxylamine hydrochloride in alcoholic KOH afforded 1-hydroxyimino-2,3,4,9-tetrahydro-1H-carbazoles (2a-e), and in acetic acid methyl isoxazolo[5,4-a]carbazole-3-carboxylates (3a-e). Ketoesters 1a-e with urea and thiourea under acidic conditions yielded a mixture of the respective 1-hydroxycarbazoles (6a-e) and 2,3,4,9-tetrahydro-1H-carbazol-1-ones (7a-e), but under basic conditions the respective 1-carbimido-and 1-thiocarbimido-2,3,4,9- tetrahydro-1H-carbazoles (8a-e and 9a-e) were formed. Plausible mechanisms are proposed.
- Martin, Arputharaj Ebenezer,Prasad, Karnam Jayarampillai Rajendra
-
-
Read Online
- An efficient and general synthesis of indolo[2,3-a]carbazoles using the Fischer indole synthesis
-
Synthetically important indolo[2,3-a]carbazoles were obtained in a one-pot reaction via Fischer indole synthesis starting from 2-amino-cyclohexanone hydrochloride and substituted arylhydrazines hydrochloride in the presence of acidic media.
- Hu, Yong-Zhou,Chen, You-Qin
-
-
Read Online
- Synthesis of tricyclic units of indole alkaloids: Application of Fischer indolization and olefin metathesis
-
Simple synthetic approaches to pyridocarbazole and azepinocarbazole derivatives have been reported via Fischer indolization, Grignard reaction and olefin metathesis as key steps. In addition, a combination Sonogashira coupling and Pauson-Khand reaction has been used to assemble extended pyridocarbazole derivative.
- Kotha, Sambasivarao,Aswar, Vikas R.,Singhal, Gaurav
-
-
Read Online
- Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles
-
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.
- Bi, Hong-Yan,Li, Cheng-Jing,Liang, Cui,Mo, Dong-Liang,Wei, Cui
-
p. 5815 - 5821
(2020/09/21)
-
- 1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF
-
The present invention relates to 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole derivative compounds and uses thereof. In particular, compounds of the invention have antibacterial activity and/or are capable of re-sensitizing methicillin-resistant Staphylococcus aureus to a P-lactam antibiotic or a combination of a P-lactam antibiotic and a P-lactamase inhibitor. The present invention also relates to a method for producing and using said compounds.
- -
-
Paragraph 0487-0488
(2020/03/05)
-
- THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION
-
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
- -
-
Page/Page column 83; 84
(2019/01/17)
-
- Design, synthesis and evaluation of hybrid of tetrahydrocarbazole with 2,4-diaminopyrimidine scaffold as antibacterial agents
-
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.
- 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)
-
- First-generation structure-activity relationship studies of 2,3,4,9-tetrahydro-1H-carbazol-1-amines as CpxA phosphatase inhibitors
-
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
- 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)
-
- USE OF A DHODH INHIBITOR IN COMBINATION WITH AN INHIBITOR OF PYRIMIDINE SALVAGE
-
Compounds and methods are provided for the treatment of pathogenic virus infections or cancer. The formulations combine an inhibitor of de novo pyrimidine synthesis, and an inhibitor of a pyrimidine salvage pathway enzyme.
- -
-
-
- A diversity-oriented approach to indolocarbazoles: Via Fischer indolization and olefin metathesis: Total synthesis of tjipanazole D and i
-
New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.
- Kotha, Sambasivarao,Saifuddin, Mohammad,Aswar, Vikas R.
-
p. 9868 - 9873
(2016/10/31)
-
- Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation
-
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.
- Shi, Hao,Guo, Tianjian,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
-
p. 2753 - 2760
(2014/04/17)
-
- Synthesis and Oxidative Cleavage of Oxazinocarbazoles: Atropselective Access to Medium-Sized Rings
-
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.
- Liu, Gu,Lancefield, Christopher S.,Lorion, Magali M.,Slawin, Alexandra M. Z.,Westwood, Nicholas J.
-
p. 2808 - 2814
(2015/02/19)
-
- 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
-
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.
- Chakraborty, Suchandra,Chattopadhyay, Gautam,Saha, Chandan
-
p. 331 - 338
(2011/06/19)
-
- Montmorillonite-KSF induced Fischer indole cyclization under microwave towards a facile entry to 1-keto-1,2,3,4-tetrahydrocarbazoles
-
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.
- Chakraborty, Suchandra,Chattopadhyay, Gautam,Saha, Chandan
-
experimental part
p. 201 - 206
(2011/03/22)
-
- Convenient and efficient synthesis of 1-oxo-1,2,3,4-tetrahydrocarbazoles via Fischer indole synthesis
-
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
- Sheng, Rong,Shen, Li,Chen, You-Qin,Hu, Yong-Zhou
-
experimental part
p. 1120 - 1127
(2009/09/08)
-
- HCV INHIBITORS
-
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.
- -
-
-
- HCV INHIBITORS
-
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.
- -
-
-
- HCV INHIBITORS
-
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.
- -
-
-
- Substituted tetrahydrocarbazoles with potent activity against human papillomaviruses
-
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.
- 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)
-
- Conformationally restrained carbazolone-containing α,γ-diketo acids as inhibitors of HIV integrase
-
Since α,γ-diketo acid (DKA) compounds were identified as potent and selective inhibitors for HIV integrase, numerous structural modification studies have been carried out to search for a clinical candidate as a supplement for the highly active antiretroviral therapy regimen. Due to the lack of structural information on inhibitor-integrase interactions, a comprehensive structure-activity relationship study is necessary. Most of the reported modification studies on the key α,γ-diketo acid pharmacophore focused on substituting the carboxylate moiety with its bioisosteres or other electron-pair bearing heterocycles. We were interested in studying the conformation and geometry of the central diketo moiety. A series of carbazolone-containing α,γ-diketo acids were designed and synthesized by applying conformational restraint onto the open-chain form of the diketo acid. These compounds showed anti-integrase activity in the low micromolar range, and integrase assay results indicated that the geometry of the diketo acid moiety is crucial to potency. Carbazol-1-one containing DKA analogs (7-8) showed a 2- to 3-fold increase in activity compared with those of carbazol-4-one containing DKA analogs (5 and 6). Alkylation of carbazol-4-one DKA nitrogen (6a-c) led to a loss of activity, suggesting this nitrogen atom may directly interact with the active site of integrase. The halogens (7b-d) and para-fluorobenzyl substituents (8a-d) on carbazol-1-one ring had little effect on potency.
- Li, Xingnan,Vince, Robert
-
p. 2942 - 2955
(2007/10/03)
-
- NOVEL CYCLOALKYL’B! CONDENSED INDOLES
-
The present invention relates to compounds of formula (I) that are useful in the treatment of human papillomaviruses, and also to the methods for the making and use of such compounds.
- -
-
-
- TETRAHYDROCARBAZOLE DERIVATIVES AND THEIR PHARMACEUTICAL USE
-
The present invention relates to novel compounds of formula (I), that are useful in the treatment of human papillomaviruses, and also to the methods for the making and use of such compounds.
- -
-
-
- TETRAHYDROCARBAZOLE DERIVATIVES AND THEIR PHARMACEUTICAL USE
-
The present invention relates to novel compounds of formula (I) that are useful in the treatment of human papillomaviruses, and also to the methods for the making and use of such compounds.
- -
-
-