Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole

Sang Ho Lee; Suhyun Kim; Min Han Yun; Yong Sup Lee; Sangnae Cho; Taegwon Oh; Pilho Kim

doi:10.1016/j.bmcl.2010.12.128

Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole

Sang Ho Lee, Suhyun Kim, Min Han Yun, Yong Sup Lee, Sangnae Cho, Taegwon Oh, Pilho Kim

Department of Microbiology

Research output: Contribution to journal › Article

28 Citations (Scopus)

Abstract

We have designed and synthesized econazole-derived nitroimidazoles to investigate the antitubercular activity of the nitroimidazole compounds. The introduction of a nitro group at the 4-position of the imidazole on econazole abolished the antitubercular activity. However, alcoholic nitroimidazoles 4 and 6 compounds were active against Mycobacterium tuberculosis (Mtb). While the MIC value of econazole was 16 μg/mL, the MIC of 6a and 6f turned out to be 0.5 μg/mL. In particular, the activity of 6f against non-replicating Mtb was as good as PA-824, which is currently in clinical phase II studies as an antitubercular agent. Overall, alcohol compounds 4 and 6 tend to be more active than ether compounds 5 and 7.

Original language	English
Pages (from-to)	1515-1518
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1016/j.bmcl.2010.12.128
Publication status	Published - 2011 Mar 1

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All Science Journal Classification (ASJC) codes

Pharmaceutical Science
Drug Discovery
Organic Chemistry
Molecular Medicine
Molecular Biology
Clinical Biochemistry
Biochemistry

Cite this

Lee, S. H., Kim, S., Yun, M. H., Lee, Y. S., Cho, S., Oh, T., & Kim, P. (2011). Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole. Bioorganic and Medicinal Chemistry Letters, 21(5), 1515-1518. https://doi.org/10.1016/j.bmcl.2010.12.128

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10.1016/j.bmcl.2010.12.128