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Aminoimidazole

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Ali Al-mourabit – One of the best experts on this subject based on the ideXlab platform.

  • Reaction of Quinones and Guanidine Derivatives: Simple Access to Bis-2-aminobenzimidazole Moiety of Benzosceptrin and Other Benzazole Motifs.
    Organic Letters, 2014
    Co-Authors: Minh Quan Tran, Ludmila Ermolenko, Pascal Retailleau, Thanh Binh Nguyen, Ali Al-mourabit
    Abstract:

    A new strategy for the synthesis of 2-aminobenzimidazol-6-ols via a reaction of quinones with guanidine derivatives is reported. Sequential application of this methodology provided a simple access to the first benzosceptrin analogue bearing a bis-2-Aminoimidazole moiety. A concomitant addition of two guanidines to the naphtho[1′,2′:4,5]imidazo[1,2-a]pyrimidine-5,6-dione, which includes the redox neutral debenzylation and guanidine-assisted cleavage of the 2-aminopyrimidine part resulted in the synthesis of the free challenging contiguous bis-2-Aminoimidazole moiety of benzosceprins in one step.

  • N-Pyridinium imidates as new sources of 2-Aminoimidazole and imidazoline derivatives
    Tetrahedron Letters, 2009
    Co-Authors: Sylvain Picon, Anne Zaparucha, Ali Al-mourabit
    Abstract:

    New 2-Aminoimidazole (2-AI) and imidazoline derivatives were obtained in three steps through the reduction of N-pyridinium imidates into 1,2-dihydropyridine imidates and oxidative addition of guanidine derivatives. Among the possible transformations, imidate substitution allows selectivity in the last deprotection step, leading to an original 2-aminoimidazolo-imidazoline skeleton.

  • Biogenetically inspired synthesis of marine C6N4 2-Aminoimidazole alkaloids: Ab initio calculations, tautomerism, and reactivity.
    Organic letters, 2004
    Co-Authors: Robert Abou-jneid, Said Ghoulami, Marie-thérèse Martin, Elise Tran Huu Dau, Nathalie Travert, Ali Al-mourabit
    Abstract:

    A simple synthesis of the fused tetrahydro-imidazopyridine 13 was accomplished via selective addition of protected guanidine to N-carbomethoxy-1,2-dihydropyridine in the presence of bromine. Base-mediated semicleavage of the aminal gave 4-substituted 2-Aminoimidazole 14. With this new method, natural marine metametabolite 3-amino-1-(2-aminoimidazol-4-yl)-prop-1-ene (1) and derivatives may now be prepared from pyridine. Ab initio calculations of the energies of tautomers I−IV and deuteration experiments have provided insight into their reactivity.

Christian Melander – One of the best experts on this subject based on the ideXlab platform.

  • Reversal of Mycobacterium tuberculosis phenotypic drug resistance by 2-Aminoimidazole-based small molecules.
    Pathogens and disease, 2014
    Co-Authors: David F. Ackart, Erick A. Lindsey, Brendan K. Podell, Roberta J. Melander, Randall J. Basaraba, Christian Melander
    Abstract:

    The expression of phenotypic drug resistance or drug tolerance serves as a strategy for Mycobacterium tuberculosis to survive in vivo antimicrobial drug treatment; however, the mechanisms are poorly understood. Progress toward a more in depth understanding of in vivo drug tolerance and the discovery of new therapeutic strategies designed specifically to treat drug-tolerant M. tuberculosis are hampered by the lack of appropriate in vitro assays. A library of 2-Aminoimidazole-based small molecules combined with the antituberculosis drug isoniazid was screened against M. tuberculosis expressing in vitro drug tolerance as microbial communities attached to an extracellular matrix derived from lysed leukocytes. Based on the ability of nine of ten 2-Aminoimidazole compounds to inhibit Mycobacterium smegmatis biofilm formation and three of ten molecules capable of dispersing established biofilms, two active candidates and one inactive control were tested against drug-tolerant M. tuberculosis . The two active compounds restored isoniazid susceptibility as well as reduced the in vitro minimum inhibitory concentrations of isoniazid in a dose-dependent manner. The dispersion of drug-tolerant M. tuberculosis with 2-Aminoimidazole-based small molecules as an adjunct to antimicrobial treatment has the potential to be an effective antituberculosis treatment strategy designed specifically to eradicate drug-tolerant M. tuberculosis .

  • Inhibition of Acinetobacter baumannii biofilm formation on a methacrylate polymer containing a 2-Aminoimidazole subunit.
    Chemical communications (Cambridge England), 2011
    Co-Authors: Lingling Peng, Joseph D. Desousa, Bruce M. Novak, Alexander A. Nevzorov, Eva R. Garland, Christian Melander
    Abstract:

    A polymeric composite containing a 2-Aminoimidazole derivative was synthesized. It was found that this polymer was resistant to biofilm colonization by Acinetobacter baumannii, no leaching of the 2-Aminoimidazole derivative was observed after 2 weeks of treatment with deionized water, and the resulting polymer was not hemolytic.

  • Modulating the development of E. coli biofilms with 2-Aminoimidazoles.
    Bioorganic & medicinal chemistry letters, 2010
    Co-Authors: Catherine S. Reed, Steven A. Rogers, Robert W. Huigens, Christian Melander
    Abstract:

    The synthesis of a 20 member 2-Aminoimidazole/triazole pilot library is reported. Each member of the library was screened for its ability to inhibit or promote biofilm development of either Escherichia coli and Acinetobacter baumannii. From this screen, E. coli-selective 2-Aminoimidazoles were discovered, with the best inhibitor inhibiting biofilm development with an IC(50) of 13μM. The most potent promoter of E. coli biofilm formation promoted biofilm development by 321% at 400μM.

Juleen R. Zierath – One of the best experts on this subject based on the ideXlab platform.

  • 5 Aminoimidazole 4 carboxamide ribonucleoside treatment improves glucose homeostasis in insulin resistant diabetic ob ob mice
    Diabetologia, 2002
    Co-Authors: Xiao-mei Song, Maj Fiedler, Dana Galuska, Jeffrey W Ryder, Maria Fernström, Alexander V Chibalin, Harriet Wallberghenriksson, Juleen R. Zierath
    Abstract:

    Aims/hypothesis: The 5′AMP-activated protproteinase is an important mediator of muscle contraction-induced glucose transport and a target for pharmacological treatment of Type II (non-insulin-dependent) diabetes mellitus. The 5′AMP-activated protproteinase can be activated by 5-Aminoimidazole-4-carboxamide ribonucleoside. We hypothesised that 5-Aminoimidazole-4-carboxamide ribonucleoside treatment could restore glucose homehomeostasis in ob/ob mice.

  • 5-Aminoimidazole-4-carboxy-amide-1-β-D-ribofuranoside treatment ameliorates hyperglycaemia and hyperinsulinaemia but not dyslipidaemia in KKAy-CETP mice
    Diabetologia, 2001
    Co-Authors: Fiedler, Juleen R. Zierath, Göran Selen, Harriet Wallberg-henriksson, Y. Liang, Kjell S. Sakariassen
    Abstract:

    Aim/hypothesis: 5-Aminoimidazole-4-carboxy-amide-1-β-d-ribofuranoside increases 5′-AMP-activated kinase activity in insulin-sensitive tissues known to control glucose homehomeostasis. We hypothesised that 5-Aminoimidazole-4-carboxy-amide-1-β-d-ribofuranoside treatment could have a beneficial effect on glucose homehomeostasis in KKAy-CETP mice, a model of Type II (non-insulin-dependent) diabetes mellitus. Our aim was to examine potential effects of acute and chronic (7-day) 5-Aminoimidazole-4-carboxy-amide-1-β-d-ribofuranoside treatment on glucose homehomeostasis in KKAy-CETP diabetic mice.

  • AICAR (5-Aminoimidazole-4-carboxamide ribonucleoside) ameliorates hyperglycemia and hyperinsulinemia in type 2 diabetic mice
    Diabetes Research and Clinical Practice, 2000
    Co-Authors: Fiedler, Xiao-mei Song, Juleen R. Zierath, Maria Fernström, Yin Liang, Göran Selen, Gunnel Klingström, Kjell S. Sakariassen
    Abstract:

    AICAR (5-Aminoimidazole-4-carboxamide ribonucleoside) ameliorates hyperglycemia and hyperinsulinemia in type 2 diabetic mice

Kjell S. Sakariassen – One of the best experts on this subject based on the ideXlab platform.

  • 5-Aminoimidazole-4-carboxy-amide-1-β-D-ribofuranoside treatment ameliorates hyperglycaemia and hyperinsulinaemia but not dyslipidaemia in KKAy-CETP mice
    Diabetologia, 2001
    Co-Authors: Fiedler, Juleen R. Zierath, Göran Selen, Harriet Wallberg-henriksson, Y. Liang, Kjell S. Sakariassen
    Abstract:

    Aim/hypothesis: 5-Aminoimidazole-4-carboxy-amide-1-β-d-ribofuranoside increases 5′-AMP-activated kinase activity in insulin-sensitive tissues known to control glucose homeostasis. We hypothesised that 5-Aminoimidazole-4-carboxy-amide-1-β-d-ribofuranoside treatment could have a beneficial effect on glucose homeostasis in KKAy-CETP mice, a model of Type II (non-insulin-dependent) diabetes mellitus. Our aim was to examine potential effects of acute and chronic (7-day) 5-Aminoimidazole-4-carboxy-amide-1-β-d-ribofuranoside treatment on glucose homeostasis in KKAy-CETP diabetic mice.

  • AICAR (5-Aminoimidazole-4-carboxamide ribonucleoside) ameliorates hyperglycemia and hyperinsulinemia in type 2 diabetic mice
    Diabetes Research and Clinical Practice, 2000
    Co-Authors: Fiedler, Xiao-mei Song, Juleen R. Zierath, Maria Fernström, Yin Liang, Göran Selen, Gunnel Klingström, Kjell S. Sakariassen
    Abstract:

    AICAR (5-Aminoimidazole-4-carboxamide ribonucleoside) ameliorates hyperglycemia and hyperinsulinemia in type 2 diabetic mice

Hans Steenackers – One of the best experts on this subject based on the ideXlab platform.

  • 2-Aminoimidazoles as potent inhibitors of contaminating brewery biofilms.
    Biofouling, 2021
    Co-Authors: Lene Jacobs, Jolien Meesters, Ilse Parijs, Geert Hooyberghs, Erik V Van Der Eycken, Bram Lories, Hans Steenackers
    Abstract:

    Cleaning and disinfection protocols are not always able to remove biofilm microbes present in breweries, indicating that novel anti-biofilm strategies are needed. The preventive activities of three in-house synthesized members of the 2-Aminoimidazole class of anti-biofilm molecules were studied against 17 natural brewery biofilms and benchmarked against 18 known inhibitors. Two 2-Aminoimidazoles belonged to the top six inhibitors, which were retested against 12 defined brewery biofilm models. For the three best inhibitors, tannic acid (n° 1), 2-Aminoimidazole imi-AAC-5 (n° 2), and baicalein (n° 3), the effect on the microbial metabolic activity was evaluated. Here, the top three inhibitors showed similar effectiveness, with baicalein possessing a slightly higher efficacy. Even though the 2-Aminoimidazole was the second-best inhibitor, it showed a lower biocidal activity than tannic acid, making it less prone to resistance evolution. Overall, this study supports the potential of 2-Aminoimidazoles as a preventive anti-biofilm strategy.

  • Evaluation of the toxicity of 5-aryl-2-Aminoimidazole-based biofilm inhibitors against eukaryotic cell lines, bone cells and the nematode Caenorhabditis elegans
    Molecules, 2016
    Co-Authors: Mirjam Fröhlich, Barbara Dovgan, Hans Steenackers
    Abstract:

    Previously, we have synthesized several series of compounds based on the 5-Aryl-2-Aminoimidazole scaffold, which showed a preventive activity against microbial biofilms. We here studied the cytotoxicity of the most active compounds of each series. First, the cytostatic activity was investigated against a number of tumor cell lines (L1210, CEM and HeLa). A subset of monosubstituted 5-Aryl-2-Aminoimidazoles showed a moderate safety window, with therapeutic indices (TIs) ranging between 3 and 20. Whereas introduction of a (cyclo-)alkyl chain at the N1-position strongly reduced the TI, introduction of a (cyclo-)alkyl chain or a triazole moiety at the 2N-position increased the TI up to 370. Since a promising application of preventive anti-biofilm agents is their use in anti-biofilm coatings for orthopedic implants, their effects on cell viability and functional behavior of human osteoblasts and bone marrow derived mesenchymal stem cells were tested. The 2N-substituted 5-Aryl-2-Aminoimidazoles consistently showed the lowest toxicity and allowed survival of the bone cells for up to 4 weeks. Moreover they did not negatively affect the osteogenic differentiation potential of the bone cells. Finally, we examined the effect of the compounds on the survival of Caenorhabditis elegans, which confirmed the higher safety window of 2N-substituted 5-Aryl-2-Aminoimidazoles.