Synthesis, Antibacterial, Anthelmintic and Anti-Inflammatory Studies of Novel Methylpyrimidine Sulfonyl Piperazine Derivatives

Mohan, N.; Sreenivasa, S.; ManojKumar, K. E.; Rao, Tadimety Madhuchakrapani; Thippeswamy, B.S.; Suchetan, P.A.

doi:10.5935/0103-5053.20140073

Cited by 9 publications

(5 citation statements)

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“…Therefore, it could be speculated that l -menthol moiety acts similarly in the biofilm and facilitates the diffusion of F105 into the biofilm matrix and probably through the cell membrane. Several researchers reported that sulfonyl-containing compounds effectively repressed the growth of Staphylococci ( Meadows and Gervay-Hague, 2006 ; Kudryavtsev et al, 2009 ; Low et al, 2011 ) suggesting antibacterial activity of the sulfonyl moiety ( Mohan et al, 2014 ; Thirukovela et al, 2017 ). In contrast, the analogs of F105 lacking either sulfonyl group (compound 3 on the Figure 1 ) or l -menthol moiety (3-chloro-5-hydroxy-4-[(4-methylphenylsulfonyl)]-2(5 H )-furanone) exhibited no activity against S. aureus ( Latypova et al, 2014 ; Kayumov et al, 2015a ) suggesting the requirement of both functional groups for bactericidal activity of F105 .…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial Effects of Sulfonyl Derivative of 2(5H)-Furanone against Planktonic and Biofilm Associated Methicillin-Resistant and -Susceptible Staphylococcus aureus

et al. 2017

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The gram-positive opportunistic bacterium Staphylococcus aureus is one of the most common causatives of a variety of diseases including skin and skin structure infection or nosocomial catheter-associated infections. The biofilm formation that is an important virulence factor of this microorganism renders the antibiotic therapy ineffective, because biofilm-embedded bacteria exhibit strongly increased tolerance to antimicrobials. Here, we describe a novel 3-chloro-5(S)-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-4-[4-methylphenylsulfonyl]-2(5H)-furanone (F105), possessing a sulfonyl group and l-menthol moiety. Minimal inhibitory and bactericidal concentration values (MIC and MBC) of F105 were 10 and 40 mg/L, respectively, suggesting F105 biocidal properties. F105 exhibits pronounced activity against biofilm-embedded S. aureus and increases the efficacy of aminoglycosides (amikacin, gentamicin, and kanamycin) and benzalkonium chloride with fractional inhibitory concentration index values of 0.33-0.44 and 0.29, respectively, suggesting an alternative external treatment option, e.g., for wound infections. Moreover, low concentrations (0.5-1.3 mg/L) of F105 reduced the MICs of these antimicrobials twofold. By using confocal laser scanning microscopy and CFU counting, we show explicitly that F105 also restores the antimicrobial activity of gentamicin and ampicillin against S. aureus biofilms by several orders of magnitude. Biofilm structures were not destroyed but sterilized, with embedded cells being almost completely killed at twofold MBC. While F105 is quite toxic (CC 50 /MBC ratio 0.2), our data suggest that the F105 chemotype might be a promising starting point for the development of complex topical agents for combined anti-staphylococcal biofilm-therapies restoring the efficacy of some antibiotics against difficult to treat S. aureus biofilm.

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Section: Discussionmentioning

confidence: 99%

Antimicrobial Effects of Sulfonyl Derivative of 2(5H)-Furanone against Planktonic and Biofilm Associated Methicillin-Resistant and -Susceptible Staphylococcus aureus

et al. 2017

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“…Antibacterial activity of synthesized compounds were assessed by Disc‐diffusion method against two bacterial strain viz S aureus and E coli . Bacterial strains were maintained on Muller‐Hinton agar medium.…”

Section: Discussionmentioning

confidence: 99%

“…Compounds 8(a-e) were purified by recrystallization using ethylacetate: n-hexane (9:1). Antibacterial activity of synthesized compounds were assessed by Disc-diffusion method [34][35][36] against two bacterial strain viz S aureus and E coli. Bacterial strains were maintained on Muller-Hinton agar medium.…”

Section: General Procedures For the Preparation Of Compounds 8(a-e)mentioning

confidence: 99%

Synthesis, biological screening, in silico study and fingerprint applications of novel 1, 2, 4‐triazole derivatives

Khan

Sreenivasa

Govindaiah

et al. 2020

Journal of Heterocyclic Chem

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A series of novel 1,2,4 triazole derivatives were synthesized by treating 4‐bromo‐2‐(4H‐1,2,4‐triazole‐3‐yl)aniline (4) with different substituted benzene sulfonyl chlorides 5(a‐f) and benzyl bromides 7(a‐e). IR, 1H‐NMR, 13C‐NMR, and mass analysis confirmed the structures of the newly synthesized compounds. All derivatives were screened for their in vitro antibacterial activity against two bacterial strains viz Escherichia coli and Staphylococcus aureus, antifungal activity against Aspergillus flavus and Candida albicans, anthelmintic activity against Pheretima posthuma and also cytotoxicity activity against MDA‐MB 231 and A375 cancer cell lines. It was found that some of the derivatives showed significant antibacterial, antifungal, anthelmintic, and cytotoxic activities when compared to respective standard drugs. Molecular docking studies have assisted the theoretical binding mode of the target molecules. Compounds were also explored for fingerprint application.

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“…Besides, sulphonyl group is often employed as an antibacterial part. 18,19 Hence, new branched molecules carrying xacin segments as the arms and bisphenylsulphonyl as the core were prepared and characterised in this study. The adsorption of the target branched molecules on copper surface was analysed by the combined calculations and experiments.…”

Section: Introductionmentioning

confidence: 99%

Inspired trifunctional adsorption films of branched molecules on copper surface for protection

Shi,

Chen,

Zhang

et al. 2024

Materials Science and Technology

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This study developed a method to realise triple resistant effects of new branched molecules for copper surface in aqueous solution. The adsorption of the studied molecules on copper surface was analysed. The results demonstrate that the copper surface adsorbed by the studied molecules showed super resistance effects on Chlorella sp., Escherichia coli and Staphylococcus aureus. The dramatic corrosive suppression of the branched compounds on copper in 0.5 M H2SO4 solution was revealed by the potentiodynamic polarisation and electrochemical impedance spectroscopy at 298 K. By establishing a simple chemical strategy to construct the branched molecules, the multiple inhibition properties of the target molecular adsorption layers on copper can be controlled on the molecular scale.

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Synthesis, Antibacterial, Anthelmintic and Anti-Inflammatory Studies of Novel Methylpyrimidine Sulfonyl Piperazine Derivatives

Cited by 9 publications

References 0 publications

Antimicrobial Effects of Sulfonyl Derivative of 2(5H)-Furanone against Planktonic and Biofilm Associated Methicillin-Resistant and -Susceptible Staphylococcus aureus

Antimicrobial Effects of Sulfonyl Derivative of 2(5H)-Furanone against Planktonic and Biofilm Associated Methicillin-Resistant and -Susceptible Staphylococcus aureus

Synthesis, biological screening, in silico study and fingerprint applications of novel 1, 2, 4‐triazole derivatives

Inspired trifunctional adsorption films of branched molecules on copper surface for protection

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