Design, synthesis, and antibiofilm activity of 2-arylimino-3-aryl-thiazolidine-4-ones

Pan, Bin; Huang, Ruoyu; Han, Shiqing; Qu, Di; Zhu, Maguang; Wei, Ping; Ying, Hanjie

doi:10.1016/j.bmcl.2010.03.013

Cited by 50 publications

(29 citation statements)

References 13 publications

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“…E coli strains were grown in Luria-Bertani (LB) broth, and staphylococcal strains were cultivated in tryptic soy broth medium (TSB; Oxoid Ltd, Basingstoke, UK). The six derivatives of Compound 2 mentioned in this report (including five reported previously [26] and one newly synthesized) are H2-10, H2-12, H2-20, H2-27, H2-28, and H2-29. These compounds were synthesized by modifying the functional groups while keeping the thiazolidione core structure intact.…”

Section: Methodsmentioning

confidence: 99%

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Thiazolidione derivatives targeting the histidine kinase YycG are effective against both planktonic and biofilm-associated Staphylococcus epidermidis

et al. 2012

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Aim: To evaluate the efficacies of six derivatives of Compound 2, a novel YycG histidine kinase inhibitor with the thiazolidione core structure in the treatment of medical device-related biofilm infections. Methods: The minimal inhibitory concentration (MIC) of the derivatives was determined using the macrodilution broth method, and the minimal bactericidal concentration (MBC) was obtained via sub-culturing 100 μL from each negative tube from the MIC assay onto drug-free Mueller-Hinton agar plates. Biofilm-killing effect for immature (6 h-old) biofilms was examined using a semiquantitative plate assay, and the effect on mature (24 h-old) biofilms was observed under a confocal laser scanning microscope (CLSM). Results: The derivatives potently suppressed the growth of Staphylococcus epidermidis. The MIC values of the derivatives H2-10, H2-12, H2-20, H2-29, H2-27, and H2-28 on S epidermidis ATCC 35984 were 24.3, 6.5, 6.2, 3.3, 3.1, and 1.5 μg/mL, respectively. The MBC values of these derivatives were 48.6, 52.2, 12.4, 52.6, 12.4, and 6.2 μg/mL, respectively. The derivatives killed all bacteria in immature (6 h-old) biofilms and eliminated the biofilm proliferation. The derivatives also displayed strong bactericidal activities toward cells in mature (24 h-old) biofilms, whereas they showed low cytotoxicity and hemolytic activity toward Vero cells and human erythrocytes. Conclusion: The bactericidal and biofilm-killing activities of the new anti-YycG compounds were significantly better than the parent Compound 2.

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Section: Methodsmentioning

confidence: 99%

“…Biofilm-killing assays Biofilm formation was detected using a semiquantitative plate assay [26] . An overnight culture of S epidermidis ATCC 35984 was diluted 1:200 into TSB medium, and incubated statically for 6 h in a polystyrene 96-well plate at 37 °C.…”

Section: Inhibition Assay For Yycg′ Autophosphorylation Activitymentioning

confidence: 99%

Thiazolidione derivatives targeting the histidine kinase YycG are effective against both planktonic and biofilm-associated Staphylococcus epidermidis

et al. 2012

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“…For example, comparatively, the 4-aminoquinoline pharmacophore has been exploited in a variety of ways to derive antimalarials [24][25][26] , but it is exclusively for one disease and has not found significant use for any other disease. The ease of synthesis of substituted thioureas [27][28][29][30][31][32][33] means that there are now hundreds of these analogues available which have not yet been characterized. 7,34 Although effective, drugs containing the thiourea functional group have been found to exhibit some toxicity.…”

Section: Introductionmentioning

confidence: 99%

Oxyhalogen-sulfur chemistry: Kinetics and mechanism of oxidation of n-acetylthiourea by aqueous bromate and acidified bromate

Chipiso¹,

Mbiya²,

Tran³

et al. 2016

S.Afr.j.chem.

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“…[1][2][3][4][5][6][7][8][9]. Recently, 2,3-diaryl-1,3-thiazolidin-4-one scaffold has been reported to possess a selective inhibition against the HIV-1 reverse transcriptase (RT) by binding to the allosteric site of the enzyme as a non-nucleoside RT inhibitor (NNRTI) [10][11][12][13][14][15][16][17], and a high activity level was observed for compounds possessing a 4,5,6-trimethylpyrimidine moiety at N-3 position [18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and HIV-RT inhibitory activity of novel thiazolidin-4-one derivatives

Chen

Guo

Yin

et al. 2011

Front. Chem. Sci. Eng.

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A series of 2-aryl-3-(4,5,6-trimethylpyrimidin-2-yl) thiazolidin-4-ones (1a-1c) and their derivatives bearing a lipophilic substituent, like acetoxy group (3a-3c), propionyloxy group (4a-4c), methyl (5d and 5e) at C-5 on thiazolidin-4-one ring were designed, synthesized and evaluated for their HIV-RT inhibitory activity. Using selfcatalyzed Pummerer reaction, compounds 3a-3c and 4a-4c were obtained in good yield (63.1%-75.2%). Preliminary anti-HIV-RT test of these derivatives indicated that compounds 1a-1c, 4b (propionyloxy group at C-5) showed moderate HIV-RT inhibitory activity and compounds 5d and 5e with methyl at C-5 showed a weak HIV-RT inhibitory activity. Structure activity relationship analysis suggested that the substituted groups on C-5 would be unfavorable to anti-HIV-RT activity and that the steric effect might play a critical role in the anti-HIV RT activity.

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Design, synthesis, and antibiofilm activity of 2-arylimino-3-aryl-thiazolidine-4-ones

Cited by 50 publications

References 13 publications

Thiazolidione derivatives targeting the histidine kinase YycG are effective against both planktonic and biofilm-associated Staphylococcus epidermidis

Thiazolidione derivatives targeting the histidine kinase YycG are effective against both planktonic and biofilm-associated Staphylococcus epidermidis

Oxyhalogen-sulfur chemistry: Kinetics and mechanism of oxidation of n-acetylthiourea by aqueous bromate and acidified bromate

Design, synthesis and HIV-RT inhibitory activity of novel thiazolidin-4-one derivatives

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