Thioamide Derivative of the Potent Antitubercular 2-(Decylsulfonyl)acetamide is Less Active Against Mycobacterium tuberculosis, but a More Potent Antistaphylococcal Agent
Hsien-Kuo Sun A B , Angel Pang C , Dylan C. Farr A , Tamim Mosaiab A , Warwick J. Britton C , Shailendra Anoopkumar-Dukie B , I. Darren Grice A , Milton J. Kiefel A , Nick P. West C D , Gary D. Grant B E and Todd A. Houston A EA Institute for Glycomics, Gold Coast Campus, Griffith University, Qld 4222, Australia.
B School of Pharmacy and Pharmacology, Gold Coast Campus, Griffith University, Qld 4222, Australia
C Centenary Institute, The University of Sydney, Sydney, NSW 2006, Australia.
D School of Chemistry and Molecular Biosciences, University of Queensland, St Lucia, Qld 4072, Australia.
E Corresponding authors. Email: g.grant@griffith.edu.au; t.houston@griffith.edu.au
Australian Journal of Chemistry 71(9) 716-719 https://doi.org/10.1071/CH18206
Submitted: 8 May 2018 Accepted: 31 August 2018 Published: 19 September 2018
Abstract
Due to the prevalence of thioamides in antibacterial compounds, we chose to convert the amide in the antitubercular compound 2-(decylsulfonyl)acetamide to a thioamide using Lawesson’s reagent to study its activity against a range of microorganisms. This derivative (8) had significantly diminished activity against tuberculosis but slightly better activity than the parent compound against the Gram positive species Staphylococcus aureus. This activity against a second major pathogen is remarkable considering the structural simplicity of these compounds.
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