Article

Antibacterial activity of synthesized 2,4,5-trisubstituted imidazole derivatives.

Division of Biochemical Science, National Chemical Laboratory, Pune 411 008, India.
Chemical Biology &amp Drug Design (Impact Factor: 2.47). 09/2008; 72(3):197-204. DOI: 10.1111/j.1747-0285.2008.00691.x
Source: PubMed

ABSTRACT Some novel chemically synthesized 2,4,5-trisubstituted imidazoles from aryl aldehydes and 1,2-diketones or alpha-hydroxyketone were screened against eight different human pathogenic bacteria and fungi. Seven compounds were found to be active against different bacteria. These compounds showed variation in activity and were found to be active against Gram-positive as well as Gram-negative bacteria. Compound 4-(4,5-diphenyl-1H-imidazol-2-yl)-phenol, 3d was the only compound which showed activity against Klebsiella pneumoniae while rest of the compounds did not show significant activity against this micro-organism. Minimum inhibitory concentrations of the compounds were in the range of 0.50 to 6.1 microg/mL and minimum bactericidal concentration ranges from 1.11 to 12.9 microg/mL. The candidature of active compounds to be an effective and novel drug was examined based on Lipinski's rule of Five which explained ClogP, LogS, H-bond acceptors, H-Bond donors and rotational bonds. Compounds 3a-d and 3f satisfies Lipinski's rule of Five and could be proposed as potent new antibacterial drugs.

10 Bookmarks
 · 
105 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: This article reports a fast, simple and efficient method to synthesize highly substituted imidazoles. Green organic synthesis is needed to face current environmental pollution. For instance the replacement of hazardous organic compounds by safe alternatives is particularly relevant. Ionic liquids are an environmentally friendly alternative to conventional organic solvents due to their unique physicochemical properties. Substituted imidazoles have been widely used to prepare pharmaceuticals. Many synthetic approaches have been developed to produce substituted imidazoles. However, despite considerable efforts only a few green methods are reported for the synthesis of highly substituted imidazoles. Here a straightforward and atom-economic approach is reported to synthesize a series 2,4,5-trisubstituted imidazoles directly from α-hydroxyketones and alcohols employing 1-methyl-3-H-imidazolium nitrate as a promoter and medium under microwave irradiation. The protocol has several advantages such as high yields of 77–91 %, short reaction times of 6–8 min, easy purification processes, and methodological simplicity due to the formation of carbon–carbon and carbon–heteroatom bonds in a single step. The methodology has been further extended towards the facile synthesis of Trifenagrel in good yield. This method provides new opportunities for the rapid screening of a wide range of compounds, either for the development of new drugs or total synthesis of natural products.
    Environmental Chemistry Letters 03/2014; · 1.62 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: In the last few decades, a lot of work has been done on heterocycles, especially the imidazole ring, to obtain a scaffold with potential pharmacological properties such as antibacterial, antifungal, anticancer, antiviral, antidiabetic and others, with lesser side effects. The search for new biologically active imidazoles continues to be an interesting area of investigation in medicinal chemistry. The present paper aims to bring together and discuss the wealth of information on antibacterial profile of imidazoles. So it can be employed for future development to obtain new potent drug molecules.
    Mini Reviews in Medicinal Chemistry 09/2013; · 2.87 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: In this work, some new 2-[(4,5-dimethyl-1-(arylamino)-1H-imidazol-2-yl)thio]-1-(aryl)ethanone derivatives were synthesized and investigated for their antibacterial, antifungal and anticancer activities. Toxicity of the most effective compounds was established by performing Brine-Shrimp lethality assay. Antifungal activity of the compounds was found to be higher than antibacterial and anticancer activities of the compounds.
    Bioorganic & medicinal chemistry letters 10/2013; · 2.65 Impact Factor