Antimicrobial activity of meta-alkoxyphenylcarbamates containing substituted N-phenylpiperazine fragment

Abstract

In the present investigation, the basic esters of meta-alkoxyphenylcarbamic acid bearing variously substituted N-phenylpiperazine fragment were screened for their in vitro antimicrobial activity against Staphylococcus aureus, Escherichia coli and Candida albicans, respectively. The most effective againstEscherichia coli was found the compound 6d (MIC=195,3 μg/mL) bearing simultaneously para-fluoro substituent at the 4-phenylpiperazin-1-yl core and meta-methoxy side chain in the lipophilic part of the molecule. From whole analyzed set of the molecules the substance 8e with propoxy side chain forming meta-alkoxyphenylcarbamoyl fragment and lipophilic, sterically bulky meta-trifluoromethyl group attached at N-phenylpiperazine moiety was evaluated as the most active against Candida albicans (MIC=97,7 μg/mL). On the contrary, all investigated structures were practically inactive against Staphylococcus aureus (MIC>1000 μg/mL)

Chemistry of Optically Active Cyanohydrins-Part 3:[1] Preparation and Reactions of (R)-2-Hydroxy-2-(naphthalen-1-yl)ethane- nitrile using (R)-Hydroxynitrile lyase from Prunus amygdalus. Antitumor and Antimicrobial Evaluation of the New Products

“…While the racemic compound (R,S)-8e showed no antibacterial activity, its optically active form (R)-8e, on the other hand, recorded high activity against the tested bacteria. This might be of a particular significance in the light of the well established correlation between the biological activity and stereochemical aspects (28) .These results also supplement to the well established correlation between the presence of the carbamate group and / or the oxazolidinone ring and the antimicrobial activity (29)(30)(31)(32) .…”

In vitro Antimicrobial Evaluation of Ortho-/meta-Alkoxyphenylcarbamic acid esters containing 4-(Pyrimidin-2-yl)piperazin-1-yl Moiey

“…Entire set of the compounds 1-4 was regarded as completely inactive against C. albicans with the MICs>1.00 mg/mL (Table 1). Following current results and the conclusions from previously published research article 14 , except of the lipophilicity enhancement and convenient steric properties, the presence of sterically bulkier substituent which has shown relatively strong electron-withdrawing effect within basic part of such alkoxyphenylcarbamic acid derivatives was considered the most important factor.…”

“…Previously in vitro tested meta-alkoxyphenylcarbamic acid esters containing 4-(3-trifluoromethylphenyl)piperazin-1-yl fragment 14 were completely inactive against given Gram-positive bacterial strain with its MIC=6.25 mg/mL regardless the number of carbon atoms which formed attached alkoxyl. This lipophilic substituent is also considered relatively sterically bulky and with relatively strong electron-withdrawing effect towards the aromate when attached.…”

Antimicrobial and larvicidal activities of 2-hydroxypyrrolidine/piperidine derivatives

“…The results revealed that above synthesized compounds exhibited good antimicrobial activity comparable to rifampicin against all tested pathogens. Antimicrobial activity of compounds containing nature of functional linkage [16] and substituted aromatic ring [17] has been reported. A series of 4-substituted 4-(1H-1,2,3-triazol-1-yl)piperidine building blocks was found to be active against against multidrug-resistant strains, especially to Staphylococcus aureus and Staphylococcus epidermidis [18].…”