Synthesis and antifungal activity of novel 5‐substituted 4‐(1,3,4‐thiadiazol‐2‐yl)benzene‐1,3‐diols

Matysiak, Joanna; Skrzypek, Alicja; Niewiadomy, Andrzej

doi:10.1002/hc.20645

Cited by 20 publications

(11 citation statements)

References 28 publications

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“…Numerous reports have highlighted the antimicrobial, anticancer, antioxidative, or anticonvulsant activities as characteristic of 1,3,4-thiadiazoles [6][7][8]. Due to these interesting features the thiadiazole-derived compounds were extensively studied in our group [9][10][11][12][13], with several 1,3,4-thiadiazole derivatives reported to possess significant acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition activities rendering them as potential anti-neurodegenerative agents [14].…”

Section: Introductionmentioning

confidence: 99%

Structural Features of 1,3,4-Thiadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin

Karcz

Matwijczuk

Kamiński

et al. 2020

IJMS

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Classical synthetic protocols were applied for the isolation of three novel 1,3,4-thiadiazole derivatives which were then complexed with the biologically important Cu(II) and Zn(II) ions. All free ligands and their corresponding complexes were characterized using a number of spectroscopic techniques including Ultraviolet-visible (UV–vis), Fluorescence, Infrared (FT-IR), tandem liquid chromatography-mass (LC-MS), X-ray diffraction (XRD), and Nuclear Magnetic Resonance (NMR) spectroscopy (1H, 13C, HSQC, HMBC). The results obtained are consistent with the formation of dihydrate complexes, in which the chelation of the metal ion occurs via one of the thiadiazole nitrogen atoms and the deprotonated hydroxyl group of the neighboring resorcynyl moiety. The Zn(II) complexes utilize a 1:1 ligand–metal ratio, while in the Cu(II) complexes the ligand–metal ratio is 2:1. Although the antibacterial testing identified moderate activity of the compounds against the tested bacterial strains and additionally modest antioxidant activity, a strong synergistic antibacterial effect against Staphylococcus aureus, using concomitant treatment of thiadiazole derivatives with the commercial antibiotic kanamycin, was observed. The most active thiadiazole derivative demonstrated a minimal inhibitory concentration (MIC) of 500 μg/mL while it was 125 μg/mL in the presence of kanamycin. Moreover, in the presence of few thiadiazole derivatives the MIC value of kanamycin decreased from 0.39 μg/mL to 0.5 μg/mL. The antioxidant activity (IC50) of the most active thiadiazole derivative was determined as 0.13 mM which was nearly three-fold lower compared to that of TROLOX (0.5 mM).

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Section: Introductionmentioning

confidence: 99%

Structural Features of 1,3,4-Thiadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin

Karcz

Matwijczuk

Kamiński

et al. 2020

IJMS

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“…albicans determined with the in vitro microdilution method 32 . In our research team, the search for molecules showing synergistic interactions with AmB was focused on a group of synthetic 1,3,4-thiadiazole derivatives, which are reported as promising antimicrobial agents 33–35 . The range and mechanism of the antifungal activity of compounds belonging to this group is poorly understood.…”

Section: Introductionmentioning

confidence: 99%

“…This compound has a relatively simple structure (Fig. 1), in which the heterocyclic ring of 1,3,4-thiadiazole is substituted by the benzene-1,3-diol in the 2-position and by the methyl group in the 5-position and is used as a scaffold for the synthesis of more biologically active derivatives possessing antifungal, antitumor, and neuroprotective potential 35–39 . As shown in model studies with 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine (DPPC) liposomes, the C1 compound molecules were located close to the polar lipid heads on the lipid-water interface and exhibited no interactions with the core part of the lipid membrane 40 .…”

Section: Introductionmentioning

confidence: 99%

Synergistic antifungal interactions of amphotericin B with 4-(5-methyl-1,3,4-thiadiazole-2-yl) benzene-1,3-diol

Chudzik

Bonio

Dąbrowski

et al. 2019

Sci Rep

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Amphotericin B (AmB) is a very potent antifungal drug with very rare resistance among clinical isolates. Treatment with the AmB formulations available currently is associated with severe side effects. A promising strategy to minimize the toxicity of AmB is reducing its dose by combination therapy with other antifungals, showing synergistic interactions. Therefore, substances that display synergistic interactions with AmB are still being searched for. Screening tests carried out on several dozen of synthetic 1,3,4-thiadiazole derivatives allowed selection of a compound called 4-(5-methyl-1,3,4-thiadiazole-2-yl) benzene-1,3-diol (abbreviated as C1), which shows strong synergistic interaction with AmB and low toxicity towards human cells. The aim of the present study was to investigate the type of in vitro antifungal interactions of the C1 compound with AmB against fungal clinical isolates differing in susceptibility. The results presented in the present paper indicate that the C1 derivative shows strong synergistic interaction with AmB, which allows the use of a dozen to several dozen times lower AmB concentration necessary for 100% inhibition of the growth of pathogenic fungi in vitro. Synergistic interactions were noted for all tested strains, including strains with reduced sensitivity to AmB and azole-resistant isolates. These observations give hope for the possibility of application of the AmB - C1 combinatory therapy in the treatment of fungal infections.

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“…Compounds: 4-(5-heptyl-1,3,4-thiadiazol-2-yl) benzene-1,3-diol (2), 4,4'-{[5,5'-(benzene-1,4-diyl)] bis(1,3,4-thiadiazol-2-yl)}di(benzene-1,3-diol) (7) and 4-(2,4-dichlorophenoxymethyl)benzene-1,3-diol (9) were prepared according to the procedure already described 19,20 .…”

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confidence: 99%

Synthesis and anticholinesterase activities of novel 1,3,4-thiadiazole based compounds

Skrzypek

Matysiak

Karpińska

et al. 2012

Journal of Enzyme Inhibition and Medicinal Chemistry

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Synthesis and antifungal activity of novel 5‐substituted 4‐(1,3,4‐thiadiazol‐2‐yl)benzene‐1,3‐diols

Abstract: alkyl, aryl, heterocyclic) 4- (1,3,4-thiadiazol-2-yl)

Cited by 20 publications

References 28 publications

Structural Features of 1,3,4-Thiadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin

Structural Features of 1,3,4-Thiadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin

Synergistic antifungal interactions of amphotericin B with 4-(5-methyl-1,3,4-thiadiazole-2-yl) benzene-1,3-diol

Synthesis and anticholinesterase activities of novel 1,3,4-thiadiazole based compounds

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