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

Research output: Contribution to journalArticle

26 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 languageEnglish
Pages (from-to)1515-1518
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number5
DOIs
Publication statusPublished - 2011 Mar 1

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Econazole
Nitroimidazoles
Mycobacterium tuberculosis
Antitubercular Agents
Ether
Alcohols

All Science Journal Classification (ASJC) codes

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

Cite this

Lee, Sang Ho ; Kim, Suhyun ; Yun, Min Han ; Lee, Yong Sup ; Cho, Sangnae ; Oh, Taegwon ; Kim, Pilho. / Synthesis and antitubercular activity of monocyclic nitroimidazoles : Insights from econazole. In: Bioorganic and Medicinal Chemistry Letters. 2011 ; Vol. 21, No. 5. pp. 1515-1518.
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Synthesis and antitubercular activity of monocyclic nitroimidazoles : Insights from econazole. / Lee, Sang Ho; Kim, Suhyun; Yun, Min Han; Lee, Yong Sup; Cho, Sangnae; Oh, Taegwon; Kim, Pilho.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 5, 01.03.2011, p. 1515-1518.

Research output: Contribution to journalArticle

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AU - Lee, Sang Ho

AU - Kim, Suhyun

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