Designing 2-aminoimidazole alkaloids analogs with anti-biofilm activities: Structure–activities relationships of polysubstituted triazoles

Linares, Denis; Bottzeck, O.; Pereira, Oswy Z.; Praud-Tabaries, Annie; Blache, Yves

doi:10.1016/j.bmcl.2011.09.050

Cited by 22 publications

(13 citation statements)

References 21 publications

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“…201 A set of compounds with variation of both the substitution pattern of the aromatic rings as well as the chain length between the triazole and the substituents were prepared from the corresponding azides and alkynes via RuAAC, using Cp*RuCl(PPh 3 ) 2 as the catalyst. Compound 131 (Fig.…”

Section: Scheme 56 Derivatives Of Capsaicin and Olvanil 200mentioning

confidence: 99%

“…Analogues of naamine A for evaluation of their biofilm inhibitory activity. 201 1,5-Disubstituted triazole derivatives of the triterpenoid oleanoilic acid have been prepared by Jannet and co-workers using Cp*RuCl(PPh 3 ) 2 as the catalyst under microwave conditions. 202 The anticancer and anti-inflammatory properties of the compounds were evaluated, and one of the prepared 1,5-isomers was found to show anticancer activity against murine breast and human colon cancer cells.…”

Section: Scheme 56 Derivatives Of Capsaicin and Olvanil 200mentioning

confidence: 99%

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Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

et al. 2016

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The ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) affords 1,5-disubstituted 1,2,3-triazoles in one step and complements the more established copper-catalyzed reaction providing the 1,4-isomer. The RuAAC reaction has quickly found its way into the organic chemistry toolbox and found applications in many different areas, such as medicinal chemistry, polymer synthesis, organocatalysis, supramolecular chemistry and the construction of 2 electronic devices. This review discusses the mechanism, scope and applications of the RuAAC reaction, covering the literature during the last 10 years. CONTENTS

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Section: Scheme 56 Derivatives Of Capsaicin and Olvanil 200mentioning

confidence: 99%

Section: Scheme 56 Derivatives Of Capsaicin and Olvanil 200mentioning

confidence: 99%

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

et al. 2016

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“…At this preliminary stage, no SAR can be dressed for such a class of lamellarin Q analogues, and further studies are needed. However, it is quite interesting to note at this stage that this compound possesses common structural features with our previously described bioactive naamine A analogues, which showed similar biologic activities : same substituents on the aromatic rings and a linker composed of a triazole heterocycle but connected differently to the two aromatic rings (Fig. ).…”

Section: Resultsmentioning

confidence: 63%

Synthesis of Lamellarin Q Analogues as Potential Antibiofilm Compounds

Praud-Tabaries

Bottzeck

Blache

2019

Journal of Heterocyclic Chem

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“…More precisely, we have shown that hemibastadins analogues (Linares et al . ; Andjouh and Blache , ) were able to inhibit the formation of biofilm of marine bacterial strains in vitro . Unfortunately, the two most potent derivatives were shown to highly affect the adhesion stage, but this action was correlated with a strong inhibition of bacterial growth.…”

Section: Introductionmentioning

confidence: 97%

Towards eco‐friendly biocides: preparation, antibiofilm activity of hemibastadin analogues

Kacou

Ouvrard

Jamet

et al. 2019

Lett Appl Microbiol

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Significance and Impact of the Study: This study reports relevant information about antibiofilm activity of original derivatives of hemibastadin alkaloids. The most active compound was shown to act as a specific anti-biofilm inhibitor without affecting viability of the targeted bacteria no more than those of the global bacterial community of a seawater sample. Taken together, these findings indicate the potentiality of such compounds to be used as original nonbiocidal molecules for designing eco-friendly antifouling solutions. AbstractThe antibiofilm activity of three hemibastadins analogues was evaluated against different marine bacterial strains through mono-species biofilms and through a multi-species model of biofilm. Results showed that compound 3 exhibited interesting antibiofilm efficiencies effective concentrations (EC 50 ) in the range of 30-100 lmol l À1 without acute toxicity against bacteria. Toxicity against nontargeted organisms was also considered showing that the compound did not affect the global bacterial community at a concentration of 75-100 lmol l À1 . These results provided baseline data concerning the toxicity of antibiofilm biocides against marine organisms.

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Designing 2-aminoimidazole alkaloids analogs with anti-biofilm activities: Structure–activities relationships of polysubstituted triazoles

Cited by 22 publications

References 21 publications

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

Synthesis of Lamellarin Q Analogues as Potential Antibiofilm Compounds

Towards eco‐friendly biocides: preparation, antibiofilm activity of hemibastadin analogues

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