Substitution of terminal amide with 1H-1,2,3-triazole: Identification of unexpected class of potent antibacterial agents
Date
2018
Authors
Bi, F.
Ji, S.
Venter, H.
Liu, J.
Semple, S.J.
Ma, S.
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Journal article
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Bioorganic and Medicinal Chemistry Letters, 2018; 28(5):884-891
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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 1. H-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 1. H-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 1. H-1,2,3-triazole-containing analogues was observed, which could open new opportunities for the development of antibacterial agents.
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Data source: Supplementary data, https://doi.org/10.1016/j.bmcl.2018.02.001
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Copyright 2018 Elsevier Ltd.