Abstract
A group of 31 of alkoxy-substituted phenylcarbamic acids with the alkoxy group inortho, meta orpara position, and methyl or ethoxymethyl attached to the ethylene moiety in position 1, including both basic ethyl esters and derivatives branched on ethylene, were evaluated forin vitro antimycobacterial activity againstMycobacterium tuberculosis, M. kansasii, andM. avium. To describe the structure-antimycobacterial activity relationships (QSARs), an approach based on a combination of the Free-Wilson analysis was used to express the influence of the substituents on the ethylene group as well as the position of the alkoxy groups on the phenyl ring and of the hydrophobicity of alkyls.In vitro antimycobacterial activity becomes higher with increasing hydrophobic properties of the alkoxy groups. Thepara- andmeta-substituted derivatives were more active than theortho-substituted ones. Substitution of ethylene in position 1 by methyl increased the activity againstM. tuberculosis, a similar substitution by ethoxymethyl increased the activity againstM. kansasii. The most active compounds were piperidinyl-1-(ethoxymethyl)ethylesters of heptoxyphenylcarbamic acids.
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This work was supported by theMinistry of Education, Youth and Sports of the Czech Republic (project no. MSM 111 600 001) and by the projectKONTAKT (78/ČR, 237/SR).
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Waisser, K., Dražková, K., Čižmárik, J. et al. A new group of potential antituberculotics: Hydrochlorides of piperidinylalkyl esters of alkoxy-substituted phenylcarbamic acids. Folia Microbiol 49, 265–268 (2004). https://doi.org/10.1007/BF02931041
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DOI: https://doi.org/10.1007/BF02931041