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Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wallGobec, Stanislav, 1970- ...Phosphonate inhibitors of antigen 85C were prepared. The inhibitors, comprising a phosphonate moiety, mycolic acid mimetic and a trehalose surrogate,contain substituted ... benzylalcohols,N-(u-hydroxyalky)phthalimide 2-phenylethanol or 4-(phthalimido)butanol as trehalose mimetics, and an alkyl chain of different lengths mimicking the mycolic acid side chain. The best compounds inhibited the mycolyltransferase activity of antigen 85C with IC50 in the low micromolar range and inhibited the growth of Mycobacterium avium in culture. The best compounds in the 3-phenoxybenzyl- and u- (phthalimido)alkoxy series, ethyl 3-phenoxybenzyl butylphosphonate (4a) and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl) methyl ethyl heptylphosphonate (5c) displayed IC50 values of 2.0 and 1.3 mM, respectively, in a mycolyltransferaseinhibition assay. In a M. avium growth inhibition assay MIC of 4a and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl nonylphosphonate (5d) were 248.8 and 84.5 mgžmL, respectivelySource: European journal of medicinal chemistry. - ISSN 0223-5234 (Vol. 42, no. 1, 2007, str. 54-63)Type of material - article, component partPublish date - 2007Language - englishCOBISS.SI-ID - 2053233
source: European journal of medicinal chemistry. - ISSN 0223-5234 (Vol. 42, no. 1, 2007, str. 54-63)
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Database name | Field | Year |
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Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
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Gobec, Stanislav, 1970- | 15284 |
Plantan, Ivan, 1977- | 25124 |
Mravljak, Janez, 1978- | 23419 |
Švajger, Urban | 26198 |
Wilson, Rosalind A. | |
Besra, Gurdyal S. | |
Soares Lousada, Susana | |
Appelberg, Rui | |
Kikelj, Danijel | 01463 |
Source: Personal bibliographies
and: SICRIS
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