Synthesis and evaluation of isatin-β-thiosemicarbazones as novel agents against antibiotic-resistant Gram-positive bacterial species

Zhang, Xu-Meng; Guo, Hao; Li, Zai-Shun; Song, Fuhang; Wang, Weimin; Dai, Huanqin; Zhang, Lixin; Jian-guo, Wang

doi:10.1016/j.ejmech.2015.06.047

Cited by 67 publications

(20 citation statements)

References 25 publications

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“…2-Hydrazolyl-4-thiazolidinones have emerged as a perceptible class of compounds, annexing thiosemicarbazones with 4-thiazolidinones, each with distinct biological activities. Thiosemicarbazones have been reported for their wide spectrum of antibacterial [1], anticancer [2,3], anti-inflammatory and antioxidant activities [4]. On the other hand, the chemical modification of compounds containing 4-thiazolidinone moiety leads to their wide appositeness as efficacious pharmacological agents, paving the way for their discernible antimicrobial [5,6], antimalarial [7], anti-HIV [8], antioxidant [9], anticancer [10][11][12][13], antiarrhythmic [14] and anti-inflammatory [15,16] activities.…”

Section: Introductionmentioning

confidence: 99%

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

Karanth

Narayana

Kodandoor

et al. 2018

Molbank

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Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as the catalyst. The structure of the title compound is determined by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectral data. In order to determine the molecular interactions with the bacterial enzyme, the title compound is further docked into the active site of the MurB protein of Staphylococcus aureus (PDB ID: 1HSK). The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. The compound is also evaluated for its antioxidant property by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging assay.

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Section: Introductionmentioning

confidence: 99%

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

Karanth

Narayana

Kodandoor

et al. 2018

Molbank

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“…Isatin has emerged as a promising nucleus and attracted increasing attention in medicinal chemistry and drug discovery over the past decade [ 10 ]. Previous literature reports indicated that isatin and its derivatives have diverse types of biological activity, including anticancer [ 11 ], antibacterial [ 12 ], antiviral [ 13 ], anticonvulsant [ 14 ], anti-inflammatory [ 15 ], and antifungal activity [ 16 ]. Notably, some isatin derivatives have been approved for clinic use such as sunitinib, toceranib, and nintedanib.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel Isatin-Thiazole Derivatives as α-Glucosidase Inhibitors

Xie

Wang

et al. 2017

Molecules

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A series of novel isatin-thiazole derivatives were synthesized and screened for their in vitro α-glucosidase inhibitory activity. These compounds displayed a varying degree of α-glucosidase inhibitory activity with IC50 ranging from 5.36 ± 0.13 to 35.76 ± 0.31 μm as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μm). Among the series, compound 6p bearing a hydroxyl group at the 4-position of the right phenyl and 2-fluorobenzyl substituent at the N1-positions of the 5-methylisatin displayed the highest inhibitory activity with an IC50 value of 5.36 ± 0.13 μm. Molecular docking studies revealed the existence of hydrophobic interaction, CH-π interaction, arene-anion interaction, arene-cation interaction, and hydrogen bond between these compounds and α-glucosidase enzyme.

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“…The minimal inhibitory concentrations (MICs) were carried out by microbroth dilution method described by the Clinical Laboratory Standards Institute [ 30 , 31 ]. A stock solution of all the target compounds was prepared with DMSO-medium (1:2), and then graded quantities of the test compounds were diluted with medium.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Biological Activity, and Apoptotic Properties of NO-Donor/Enmein-Type ent-Kauranoid Hybrids

Han

et al. 2016

IJMS

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Herein, we reported on a series of synthetic nitric oxide-releasing enmein-type diterpenoid hybrids (9a–i). All the target compounds showed potent antibacterial activity against selected Gram-positive bacteria S. aureus and B. subtilis. The antiproliferative activity against human tumor K562, MGC-803, CaEs-17 and Bel-7402 cells, and human normal liver cells L-02 was tested and the structure activity relationships (SARs) were also concluded. Compounds 9b and 9d showed the best activity against S. aureus and B. subtilis with the same minimal inhibitory concentrations (MICs) of 4 and 2 μg/mL, respectively. The derivative 9f displayed IC50 values of 1.68, 1.11, 3.60 and 0.72 μM against the four cancer cell lines above and 18.80 μM against normal liver cells L-02; meanwhile, 9f also released a high level of NO at the time point of 60 min of 22.24 μmol/L. Furthermore, it was also found that 9f induced apoptosis via the mitochondria-related pathway and arrested cell cycle of Bel-7402 cells at S phase. These findings might be important to explore new chemical entities for the main causes of in-hospital mortality of S. aureus infection, combined with a solid tumor.

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Synthesis and evaluation of isatin-β-thiosemicarbazones as novel agents against antibiotic-resistant Gram-positive bacterial species

Cited by 67 publications

References 25 publications

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel Isatin-Thiazole Derivatives as α-Glucosidase Inhibitors

Synthesis, Biological Activity, and Apoptotic Properties of NO-Donor/Enmein-Type ent-Kauranoid Hybrids

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