Design, synthesis and antimycobacterial activity of imidazo[1,5-a]quinolines and their zinc-complexes

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Abstract

Tuberculosis has remained one of the world's deadliest infectious diseases. The complexity and numerous adverse effects of current treatment options as well as the emergence of multi-drug resistant M. tuberculosis (Mtb) demand research and innovation efforts to yield new anti-mycobacterial agents. In this study, we synthesized a series of imidazo[1,5-a]quinolines, including 4 new analogs, and evaluated their activity against Mtb. Inspired by previous studies, we also designed 8 compounds featuring a coordinated metal ion, determined their absolute configuration by single-crystal X-ray diffraction and included them in the bioactivity study. Remarkably, the metal complexation of 5c with either Zn2+ or Fe2+ increased the Mtb inhibitory activity of the compound 12.5-fold and reduced its cytotoxicity. Ultimately, out of the 21 analyzed imidazo[1,5-a]quinoline analogs, two zinc complexes (C1 and C7) showed the strongest, specific activity against Mtb H37Rv in vitro (IC90 = 7.7 and 17.7 μM).

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APA

Marner, M., Kulhanek, N., Eichberg, J., Hardes, K., Molin, M. D., Rybniker, J., … Göttlich, R. (2024). Design, synthesis and antimycobacterial activity of imidazo[1,5-a]quinolines and their zinc-complexes. RSC Medicinal Chemistry, 15(5), 1746–1750. https://doi.org/10.1039/d4md00086b

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