Substitution of terminal amide with 1H-1,2,3-triazole: Identification of unexpected class of potent antibacterial agents |
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Authors: | Fangchao Bi Shengli Ji Henrietta Venter Jingru Liu Susan J Semple Shutao Ma |
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Institution: | 1. Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, Jinan 250012, China;2. ReaLi Tide Biological Technology (Weihai) Co. Ltd., East Longhai Road & South Yangguang Road, Nanhai New District, Weihai 264207, China;3. School of Pharmacy & Medical Sciences, Sansom Institute for Health Research, University of South Australia, GPO Box 2471, Adelaide 5001, Australia |
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Abstract: | 3-Methoxybenzamide (3-MBA) derivatives have been identified as novel class of potent antibacterial agents targeting the bacterial cell division protein FtsZ. As one of isosteres for the amide group, 1,2,3-triazole can mimic the topological and electronic features of the amide, which has gained increasing attention in drug discovery. Based on these considerations, we prepared a series of 1H-1,2,3-triazole-containing 3-MBA analogues via isosteric replacement of the terminal amide with triazole, which had increased antibacterial activity. This study demonstrated the possibility of developing the 1H-1,2,3-triazole group as a terminal amide-mimetic element which was capable of both keeping and modulating amide-related bioactivity. Surprisingly, a different action mode of these new 1H-1,2,3-triazole-containing analogues was observed, which could open new opportunities for the development of antibacterial agents. |
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Keywords: | Terminal amide Mimic Antibacterial agents Corresponding author |
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