- Selective Oxidation of Canthines to Canthin-6-ones with Triethylbenzylammonium Permanganate
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Oxidation of canthines, prepared from intramolecular inverse electron demand Diels-Alder reactions of indole with tethered triazines, produced the corresponding canthin-6-ones regiospecifically, with no detected canthin-4-ones.
- Li, Jia-He,Snyder, John K.
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- A total synthesis of 1-methoxycanthin-6-one: An efficient one-pot synthesis of the canthin-6-one skeleton from β-carboline-1-carbaldehyde
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A total synthesis of naturally occurring 1-methoxycanthin-6-one is described. In this synthesis, we achieved one-pot conversion from β-carboline-1-carbaldehyde to the canthin-6-one skeleton by the sequential addition of lithium ketene acetal in LiHMDS solution followed by the addition of EtOH in the reaction mixture.
- Suzuki, Hideharu,Adachi, Makoto,Ebihara, Yuki,Gyoutoku, Hiroshi,Furuya, Hinako,Murakami, Yasuoki,Okuno, Hiroaki
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- Solution phase and nanoparticular biosynthetically inspired interconnections in the canthin-6-one β-carboline series and study of phenotypic properties on C. elegans
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Based on the biosynthetic line of canthin-6-one alkaloids from their simple precursors such as tryptamine, the present work is focused on the study of alternative protocol of the Bischler-Napieralski reaction and has led to a full coverage of the different biosynthetic intermediates. Nanoparticles were also prepared as mimics of biosynthetic assembly lines and some interesting biological results in term of chemical ecology are also reported. Canthin-6-one, a particular representative β-carboline alkaloid, was targeted for synthesis keeping in mind its biosynthetic origin. In fact, several biosynthetic intermediates were synthesized and nanoparticular mimicry of key steps was also achieved permitting further evaluation of biological properties for this class of alkaloids. Copyright
- Cebrian-Torrejon, Gerardo,Mackiewicz, Nicolas,Vazquez-Manrique, Rafael P.,Fournet, Alain,Figadere, Bruno,Nicolas, Julien,Poupon, Erwan
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- Cantffln - 6 - quaternary ammonium salt and its preparation method and application
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The invention relates to a canthium dicoccum-6-one quaternary ammonium salt and a preparation method and an application thereof. The structural formula of the compound is shown in a formula (1) in the specification, wherein R is ethyl, propyl, isopropyl, allyl, normal-butyl, isobutyl, normal-amyl, normal-octyl, unsubstituted benzyl or substituted benzyl substituted by a hydrogen atom, methyl, bromomethyl, trifluoromethyl, benzyloxyl, a fluorine atom or a chlorine atom; X is chlorine, bromine or iodine. The application is that of the compound for preparing antibacterial drugs.
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- Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones
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An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (μg·mL-1) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (μg·mL-1) against Staphylococcus aureus.
- Dai, Jiang-Kun,Dan, Wen-Jia,Li, Na,Du, Hong-Tao,Zhang, Ji-Wen,Wang, Jun-Ru
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p. 580 - 583
(2016/01/09)
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- USE OF CANTHIN-6-ONE AND ITS ANALOGS IN THE TREATMENT OF MYCOBACTERIA-LINKED PATHOLOGIES ( amended
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The present invention relates to the use, for the preparation of a medicament intended for the treatment or the prevention of pathologies linked to, or caused by mycobacteria, of at least one of the compounds of the following formula (I): in which B represents in particular a nitrogen atom, and R1, R2, R3, R4, R5, R6, R7 and R8 represent in particular a hydrogen atom.
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- Two-step total syntheses of Canthin-6-one alkaloids: New one-pot sequential Pd-catalyzed Suzuki-Miyaura coupling and Cu-catalyzed amidation reaction
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Chemical Equation Presented Canthin-6-one (1) and nine analogues including the naturally occurring 9-methoxycanthin-6-one (2) and amaroridine (3) are prepared rapidly and in high yields via a convergent non-classical strategy that focuses on construction of the central ring B. The strategy relies on concomitant Pd-catalyzed Suzuki-Miyaura C-C coupling followed by a Cu-catalyzed C-N coupling that can be achieved either stepwise or in a new one-pot protocol starting from the appropriate 8-bromo-1,5-naphthyrldine.
- Gollner, Andreas,Koutentis, Panayiotis A.
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supporting information; experimental part
p. 1352 - 1355
(2010/06/11)
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- Synthesis and evaluation of β-carbolinium cations as new antimalarial agents based on π-delocalized lipophilic cation (DLC) hypothesis
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Several β-carbolines including naturally occurring substances and their corresponding cationic derivatives were synthesized and evaluated for antimalarial (antiplasmodial) activity in vitro and in vivo. A tetracyclic carbolinium salt was elucidated for antileishmanial and antitrypanosomal activities in vitro as well as antiplasmodial activity. Quarternary carbolinium cations showed much higher potencies in vitro than electronically neutral β-carbolines and a good correlation was observed between π-delocalized lipophilic cationic (DLC) structure and antimalarial efficacy. β-Carbolinium compounds exhibit medium suppressive activity in vivo against rodent malaria.
- Takasu, Kiyosei,Shimogama, Tsubasa,Saiin, Chalerm,Kim, Hye-Sook,Wataya, Yusuke,Brun, Reto,Ihara, Masataka
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p. 653 - 661
(2007/10/03)
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- Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities
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Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1-3 from the canthin-6-one series were characterized. Derivatives 7-28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one did not show better antifungal activities. 2005 American Chemical Society and American Society of Pharmacognosy.
- Soriano-Agaton, Flor,Lagoutte, Delphine,Poupon, Erwan,Roblot, Francois,Fournet, Alain,Gantier, Jean-Charles,Hocquemiller, Reynald
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p. 1581 - 1587
(2008/09/17)
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- Single Electron Transfer Induced Total Synthesis of Canthin-6-one
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The cytotoxic alkaloid canthin-6-one was synthesized from harmalane in a short sequence (six steps) with good overall yield (18 percent) using a single electron transfer (SET) induced radical cationic hetero [4+2] cycloaddition as high yielding key step.
- Roessler, Ulrich,Blechert, Siegfried,Steckhan, Eberhard
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p. 7075 - 7078
(2007/10/03)
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- Selenium Dioxide Oxidations in the Indole Area. Synthesis of β-Carboline Alkaloids
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A number of different piperidoindole systems have been subjected to oxidation with selenium dioxide.The bonding between the indole and piperidine unit has been varied to provide different systems, the oxidation of which has led to formation of either 2-acyl- or 3-acylindoles or fully aromatic β-carbolines, depending on the substrate chosen.The pattern of reactivity observed was in complete agreement with the ene mechanism proposed for selenium dioxide oxidations, and this can be employed to predict the regiochemistry of the oxidation.Use of this technology has resulted in a two-step synthesis of the indole alkaloid canthin-6-one (30a).
- Cain, M.,Campos, O.,Guzman, F.,Cook, J.M.
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p. 907 - 913
(2007/10/02)
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- SELENIUM DIOXIDE OXIDATIONS IN THE β-CARBOLINE AREA
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The reaction of 1-ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 11 with selenium dioxide has resulted in the synthesis of the β-carboline alkaloids, 1-acetyl-3-methoxycarbonyl-β-carboline 14 and 1-acetyl-β-carboline 15.Application of this technol
- Campos, Olivia,DiPierro, Mike,Cain, Michael,Mantei, Robert,Gawish, Ali,Cook, James M.
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p. 975 - 984
(2007/10/02)
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