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Synthesis and antitubercular activity of monocyclic nitroimidazoles: insights from econazole

Authors
 Sang-Ho Lee  ;  Suhyun Kim  ;  Min-Han Yun  ;  Yong Sup Lee  ;  Sang-Nae Cho  ;  Taegwon Oh  ;  Pilho Kim 
Citation
 BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, Vol.21(5) : 1515-1518, 2011 
Journal Title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN
 0960-894X 
Issue Date
2011
MeSH
Antifungal Agents/chemical synthesis ; Antifungal Agents/pharmacology ; Antitubercular Agents/chemical synthesis* ; Antitubercular Agents/pharmacology ; Cyclization ; Drug Design* ; Econazole/chemistry* ; Econazole/pharmacology ; Microbial Sensitivity Tests ; Molecular Structure ; Nitroimidazoles/chemical synthesis* ; Nitroimidazoles/pharmacology
Keywords
Tuberculosis ; Econazole ; Anaerobic activity ; Nitroimidazole
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.
Full Text
http://www.sciencedirect.com/science/article/pii/S0960894X10018925
DOI
10.1016/j.bmcl.2010.12.128
Appears in Collections:
1. College of Medicine (의과대학) > Research Institute (부설연구소) > 1. Journal Papers
1. College of Medicine (의과대학) > Dept. of Microbiology (미생물학교실) > 1. Journal Papers
Yonsei Authors
Oh, Tae Gwon(오태권)
Cho, Sang Nae(조상래)
URI
https://ir.ymlib.yonsei.ac.kr/handle/22282913/94044
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