Ueber Carbazol

Graebe, C.; Glaser, C.

doi:10.1002/jlac.18721630305

Cited by 27 publications

(41 citation statements)

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“…and antiCandida biofilm activity, as reported in this study for Nalkylated 3,6-dihalogenocarbazoles and in particular compound (22), are promising molecules to be investigated as novel antimycotics. Other interesting carbazoles with potent antifungal activity against C. albicans at micromolar concentrations are compounds (5), (9), (10), (11) and (13), all characterized by MIC against C. albicans < 16 M (Tables 1 and 2). Whether these potent antifungal carbazoles are also active against Candida biofilms should be further investigated.…”

Section: Discussionmentioning

confidence: 99%

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Antifungal Carbazoles

Thevissen¹,

Marchand²,

Chaltin³

et al. 2009

CMC

106

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Carbazole derivatives are well known for their various pharmacological activities, including anti-HIV, anticancer, antibacterial and antifungal activities. This review will focus on carbazoles that possess antifungal activity against Candida albicans, the major human fungal pathogen. In our search for new fungicidal compounds, we identified a series of substituted carbazoles, termed N-alkylated 3,6-dihalogenocarbazoles, that exhibit fungicidal activity against C. albicans and the emerging pathogen Candida glabrata. The most potent fungicidal compounds of this series were characterized by minimal fungicidal concentration (MFC) between 8.5 and 25 microM. To analyse the structural determinants for fungicidal activity of these carbazole derivatives, we selected 10 such derivatives and performed further analyses. Interestingly, some of these N-alkaylated 3,6-dihalogenocarbazoles were active against Candida biofilms grown in microtiterplates. In this review, we will further discuss the putative therapeutic potential of the antifungal carbazole compounds as antimycotics.

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Section: Discussionmentioning

confidence: 99%

“…Carbazole was isolated first from coal tar in 1872 by Graebe and Glaser [11]. In 1965, Chakraborty et al described the isolation and antibiotic properties of murrayanine from the curry-leef tree Murraya koenigii [12].…”

Section: Sourcementioning

confidence: 99%

Antifungal Carbazoles

Thevissen¹,

Marchand²,

Chaltin³

et al. 2009

CMC

106

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“…Carbazole was first isolated and characterized by Graebe and Glaser, which employed a high‐boiling coal tar distillate, in 1872 [1] . In the same year, Braun and Greiff reported a synthesis using aniline as starting material and intense heating in the course of a distillation process, [2] which was confirmed by Graebe and additionally refined employing diphenylamine as substrate in order to achieve higher yields [3] .…”

Section: Methodsmentioning

confidence: 95%

Electrochemical Synthesis of Carbazoles by Dehydrogenative Coupling Reaction

Kehl

Schupp

Breising

et al. 2020

Chemistry A European J

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Ac onstant current protocol, employing undivided cells, ar emarkably low supporting electrolyte concentration,i nexpensive electrode materials, and as traightforward precursor synthesise nabling an ovel access to Nprotected carbazoles by anodic N,C bond formation using directlyg enerated amidyl radicals is reported. Scalability of the reaction is demonstrateda nd an easy deblocking of the benzoyl protecting group is presented. Carbazole was first isolated and characterizedb yG raebea nd Glaser,w hich employed ah igh-boiling coal tar distillate, in 1872. [1] In the same year,B raun and Greiffr eported as ynthesis using aniline as starting material and intense heatingi nt he course of ad istillation process, [2] which was confirmed by Graebea nd additionally refined employing diphenylamine as substrate in order to achieveh igher yields. [3] The relevance of this compound class can be perceived when its potentialu se in the pharmaceutical sector [4] due to their anti-Alzheimer, [5] antibacterial, [6] fungicidal, [7] antitubercular, [8] antitumor properties, [9] or in the technicala ssignment [10] is taken into account. Since the discoveryo fc arbazole, reams of methods tackling different moieties in order to build up this particular scaffold were reported. [11] Onec onvenient and straightforward access is by ac yclizationr eactionv ia aC ,N bond formation. Classical strategies utilizingt his approach are usually in demando f metal catalysis (Pd, [12] Cu, [13, 14] Ir, [15] Rh [16]), oxidizers, [13] pre-functionalization, [17] or strongly elevated temperatures [18] which result in several drawbacks. On the one hand, leastwise stoichiometric amountso fo xidizers,t oxic and partially expensive metal complexes, and essential leaving groups evoke reagent Scheme1.Conventional approaches and our electrochemical access to Nprotectedc arbazoles. TFA = trifluoroacetic acid;EDC = 1,2-dichloroethane; CPE = constant potential electrolysis;CCE = constant current electrolysis.

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“…Carbazoles are aromatic heterocyclic organic compounds first isolated from coal tar [112]. Carbazole alkaloids have been isolated form various plants and microorganisms.…”

Section: Novel Anti-biofilm Agentsmentioning

confidence: 99%

Anti-Biofilm Strategies: How to Eradicate Candida Biofilms?

Bink¹,

Pellens²,

Cammue

et al. 2011

TOMYCJ

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In nature, microorganisms prefer to reside in structured microbial communities, termed biofilms, rather than as free-floating planktonic cells. Advantageous for the microorganisms, but disadvantageous for human health, is the increased resistance/tolerance of the biofilm cells to antimicrobial treatment. In clinically relevant biofilms, Candida albicans is one of the most frequently isolated microorganisms in biofilms. This review primarily elaborates on the activity of the currently used antimycotics against Candida biofilms, the potential of antifungal lock therapy and sheds more light on new promising compounds resulting from the gradual shift of anti-biofilm research activities to natural products, plants and their extracts.

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Ueber Carbazol

Cited by 27 publications

References 0 publications

Antifungal Carbazoles

Antifungal Carbazoles

Electrochemical Synthesis of Carbazoles by Dehydrogenative Coupling Reaction

Anti-Biofilm Strategies: How to Eradicate Candida Biofilms?

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