The Synthesis and Characterization of some New Thioureides of 2-(4-Methyl-phenoxymethyl)benzoic Acid with Antimicrobial Activity

Limban, Carmen; Missir, Alexandru-Vasile; Chiriţă, Ileana Cornelia; Niţulescu, George Mihai; Ilie, Corina; Cãproiu, Miron Teodor

doi:10.37358/rc.08.11.2012

Cited by 2 publications

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“…Various urea, thiourea and acylthiourea derivatives containing ( R )-2-amino-1-butanol were evaluated against Mycobacterium tuberculosis stains H37Rv and strain 43, with acylthiourea derivatives showing the best anti-tuberculosis effect [5]. Some 2-(phenoxymethyl)benzoyl thiourea derivatives showed promising antibacterial properties [6]. Several pyrazole-4-carbonyl thiourea derivatives demonstrated good antibacterial effects, especially on Klebsiella pneumonia [7,8].…”

Section: Introductionmentioning

confidence: 99%

Biopharmaceutical Profiling of New Antitumor Pyrazole Derivatives

et al. 2014

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Abstract:Several new pyrazole derivatives have demonstrated promising antiproliferative and cytotoxic effects, but their poor solubility raised concerns over possible biopharmaceutical limitations. In order to improve their pharmaceutical potential we performed the biopharmaceutical profiling for nine pyrazole compounds using in vitro and computational methods. The experimental solubility was determined in five different media using a validated HPLC method. Although the experimental solubility was lower than the predicted one, a good linear relationship was observed. The results also indicated a minimal impact of endogenous tensioactives on solubility, suggesting dissolution rate limited absorption. The in silico experiments were focused on identification of molecular determinants of solubility, evaluation of drug-likeness, prediction of in vivo absorption based on mechanistic models, as well as identification of the main factors that could impact on the oral bioavailability. The results suggested that dose, solubility and particle size are the main determinants of absorption, whereas permeability has little effect, confirming the BCS Class II behavior of the compounds. The present investigation was able to rank the tested compounds in terms of biopharmaceutical behavior, and indicated the B3 series compounds as having a more favorable absorption profile making them the main candidates for advance to the pre-clinical in vivo studies.

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Section: Introductionmentioning

confidence: 99%

Biopharmaceutical Profiling of New Antitumor Pyrazole Derivatives

et al. 2014

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“…We also studied the cytototoxicity of the tested compounds by flow cytometry and annexin V assay. In previous papers [ 1 , 2 , 3 , 4 ] we have presented the synthesis and characterization of some other thioureides of 2-phenoxymethylbenzoic acid, either unsubstituted or substituted with a methoxy or methyl group. We have now extended our research to the preparation and evaluation of the antimicrobial activity of some new thioureides of 2-(4-chlorophenoxymethyl)-benzoic acid.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Some New Thioureides Derived from 2-(4-Chlorophenoxymethyl)benzoic Acid

et al. 2008

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We report here the characterisation of eight newly synthesized thioureides of 2-(4-chlorophenoxymethyl)-benzoic acid and the evaluation of the in vitro antimicrobial activity of the new compounds against Gram-positive [Listeria monocytogenes, Staphylococcus aureus, Bacillus subtilis], Gram-negative [Psedomonas aeruginosa, Escherichia coli, Salmonella enteritidis], as well as Candida spp., using both reference and clinical multidrug resistant strains to establish the minimal inhibitory concentration (MIC) values. Our results showed that the tested compounds exhibited specific antimicrobial activities, both concerning the spectrum of antimicrobial activity and the corresponding MIC values, which ranged widely between 1024 and 32 μg/mL, depending on the nature and position of the substituents on the benzene ring. The most active compounds were N-[2-(4-chlorophenoxymethyl)-benzoyl]-N'-(2,6-dichlorophenyl)-thiourea (5g) and N-[2-(4-chlorophenoxymethyl)-benzoyl]-N'-(4-bromophenyl)-thiourea (5h), which showed a broad spectrum of antimicrobial activity against enterobacterial strains (E. coli and S. enteritidis), P. aeruginosa, S. aureus and Candida spp. All the tested compounds except 5f were highly active against S. aureus (MIC=32 μg/mL), suggesting their possible use in the treatment of MRSA infections. Four of compounds also exhibited antifungal activity (MIC =256-32 μg/mL) against C. albicans, but L. monocytogenes as well as B. subtilis were resistant to all tested compounds. Our studies thus demonstrated that among other biological activities, the thioureides of 2-(4-chlorophenoxymethyl)-benzoic acid also exhibit selective and effective antimicrobial properties that could lead to the selection and use of these compounds as efficient antimicrobial agents, especially for the treatment of multidrug resistant infections.

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The Synthesis and Characterization of some New Thioureides of 2-(4-Methyl-phenoxymethyl)benzoic Acid with Antimicrobial Activity

Cited by 2 publications

References 1 publication

Biopharmaceutical Profiling of New Antitumor Pyrazole Derivatives

Biopharmaceutical Profiling of New Antitumor Pyrazole Derivatives

Antimicrobial Activity of Some New Thioureides Derived from 2-(4-Chlorophenoxymethyl)benzoic Acid

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