title: Antimicrobial effect of para-alkoxyphenylcarbamic acid esters containing substituted N-phenylpiperazine moiety.
abstract: In current research, nine basic esters of para-alkoxyphenylcarbamic acid with incorporated 4-(4-fluoro-/3-trifluoromethylphenyl)piperazin-1-yl fragment, 6i-6m and 8f-8i, were screened for their in vitro antimicrobial activity against Candida albicans, Staphylococcus aureus and Escherichia coli, respectively. Taking into account the minimum inhibitory concentration assay (MIC), as the most active against given yeast was evaluated 8i (MIC = 0.20 mg/mL), the most lipophilic structure containing para-butoxy and trifluoromethyl substituents. Investigating the efficiency of the compounds bearing only a single atom of fluorine and appropriate para-alkoxy side chain against Candida albicans, the cut-off effect was observed. From evaluated homological series, the maximum of the effectiveness was noticed for the stucture 6 k (MIC = 0.39 mg/mL), containing para-propoxy group attached to phenylcarbamoyloxy fragment, beyond which the compounds ceased to be active. On the contrary, all the tested molecules were against Staphylococcus aureus and Escherichia coli (MICs > 1.00 mg/mL) practically inactive.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Bratislava, Slovak Republic.
authors.forename: Ivan
authors.initials: I
authors.lastname: Malík
authors.forename: Marián
authors.initials: M
authors.lastname: Bukovský
authors.forename: Fils
authors.initials: F
authors.lastname: Andriamainty
authors.forename: Jana
authors.initials: J
authors.lastname: Gališinová
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects*; D002219:Carbamates / Q000737:chemistry / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects*; D004952:Esters / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010879:Piperazines / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D002219:Carbamates; D004952:Esters; D010879:Piperazines; C031503:phenylpiperazine; C059692:phenylcarbamic acid
keywords: Candida albicans; phenylcarbamates; substituted N-phenylpiperazines