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Development of Cyclobutene‐ and Cyclobutane‐Functionalized Fatty Acids with Inhibitory Activity against Mycobacterium tuberculosis
Author(s) -
Sittiwong Wantanee,
Zinniel Denise K.,
Fenton Robert J.,
Marshall Darrell D.,
Story Courtney B.,
Kim Bohkyung,
Lee JiYoung,
Powers Robert,
Barletta Raúl G.,
Dussault Patrick H.
Publication year - 2014
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201402067
Subject(s) - mycobacterium tuberculosis , cyclobutane , mycobacterium smegmatis , cyclobutanes , isoniazid , chemistry , tuberculosis , microbiology and biotechnology , minimum inhibitory concentration , mycobacterium , stereochemistry , bacteria , biology , antimicrobial , genetics , medicine , organic chemistry , ring (chemistry) , pathology
Eleven fatty acid analogues incorporating four‐membered carbocycles (cyclobutenes, cyclobutanes, cyclobutanones, and cyclobutanols) were investigated for the ability to inhibit the growth of Mycobacterium smegmatis ( Msm ) and Mycobacterium tuberculosis ( Mtb ). A number of the analogues displayed inhibitory activity against both mycobacterial species in minimal media. Several of the molecules displayed potent levels of inhibition against Mtb , with MIC values equal to or below those observed with the anti‐tuberculosis drugs D ‐cycloserine and isoniazid. In contrast, two of the analogues that display the greatest activity against Mtb failed to inhibit E. coli growth under either set of conditions. Thus, the active molecules identified herein may provide the basis for the development of anti‐mycobacterial agents against Mtb .