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    Synthesis, antibacterial and anti-MRSA activity, in vivo toxicity and a structure-activity relationship study of a quinoline thiourea


    Dolan, Niamh and Gavin, Declan P. and Eshwika, Ahmed and Kavanagh, Kevin and McGinley, John and Stephens, John C. (2016) Synthesis, antibacterial and anti-MRSA activity, in vivo toxicity and a structure-activity relationship study of a quinoline thiourea. Bioorganic and Medicinal Chemistry Letters, 26 (2). pp. 630-635. ISSN 0960-894X

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    Abstract

    We report the synthesis, antibacterial evaluation of a series of thiourea-containing compounds. 1-(3,5-Bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)-((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea 5, was the most active against a range of Gram-positive and Gram-negative bacteria, and exhibited bacteriostatic activity against methicillin resistant Staphylococcus aureus (MRSA) comparable to that of the well-known antibacterial agent vancomycin. Quinoline thiourea 5 was subjected to a detailed structure–activity relationship study, with 5 and its derivatives evaluated for their bacteriostatic activity against both Gram-negative and Gram-positive bacteria. A number of structural features important for the overall activity of quinoline thiourea 5 have been identified. A selection of compounds, including 5, was also evaluated for their in vivo toxicity using the larvae of the Greater wax moth, Galleria mellonella. Compound 5, and a number of derivatives, were found to be non-toxic to the larvae of Galleria mellonella. A new class of antibiotic can result from the further development of this family of compounds.

    Item Type: Article
    Keywords: MRSA; Antibacterial; Quinoline; Thiourea; Structure activity relationship;
    Academic Unit: Faculty of Science and Engineering > Biology
    Faculty of Science and Engineering > Chemistry
    Item ID: 10746
    Identification Number: https://doi.org/10.1016/j.bmcl.2015.11.058
    Depositing User: Dr John Stephens
    Date Deposited: 24 Apr 2019 14:15
    Journal or Publication Title: Bioorganic and Medicinal Chemistry Letters
    Publisher: Elsevier
    Refereed: Yes
    URI:

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