Design, synthesis and anti-bacterial evaluation of novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety

Wan, Jin‐Lin; Gan, Yi‐Yuan; Hu, Weinan; Meng, Jiao; Tian, Kun; Li, Xiaoqin; Wu, Shou‐Qun; Xu, Yunbi; Ouyang, Gangfeng; Wang, Zhenchao

doi:10.1080/10426507.2018.1436546

Cited by 7 publications

(4 citation statements)

References 29 publications

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“…After allowing the mixture to come to room temperature, it was stirred for around 8 h at room temperature. After completion of the reaction, the resulting solids were collected by filtration, washed with distilled H 2 O (3 × 20 ml), and recrystallized from MeOH/H 2 O to yield the title compound (2.66 g, 93.66%, pale-yellow, melting point: 116–118 °C) 78 , 79 .…”

Section: Experimental Protocolsmentioning

confidence: 99%

New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

Ibrahim

Fouda

Elgammal

et al. 2022

Sci Rep

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The emergence of multidrug-resistant microbes and the propagation of cancer cells are global health issues. The unique properties of chitosan and its derivatives make it an important candidate for therapeutic applications. Herein, a new thiadiazole derivative, 4-((5-(butylthio)-1,3,4-thiadiazol-2-yl) amino)-4-oxo butanoic acid (BuTD-COOH) was synthesized and used to modify the chitosan through amide linkages, forming a new thiadiazole chitosan derivative (BuTD-CH). The formation of thiadiazole and the chitosan derivative was confirmed by FT-IR, 1H/13C-NMR, GC–MS, TGA, Elemental analysis, and XPS. The BuTD-CH showed a high antimicrobial effect against human pathogens Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, and Candida albicans with low MIC values of 25–50 μg ml−1 compared to unmodified chitosan. The in-vitro cytotoxicity of BuTD-CH was evaluated against two cancer cell lines (MCF-7 and HepG2) and one normal cell (HFB4) using the MTT method. The newly synthesized derivatives showed high efficacy against cancerous cells and targeted them at low concentrations (IC50 was 178.9 ± 9.1 and 147.8 ± 10.5 μg ml−1 for MCF-7 and HepG2, respectively) compared with normal HFB4 cells (IC50 was 335.7 ± 11.4 μg ml−1). Thus, low concentrations of newly synthesized BuTD-CH could be safely used as an antimicrobial and pharmacological agent for inhibiting the growth of human pathogenic microbes and hepatocellular and adenocarcinoma therapy.

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Section: Experimental Protocolsmentioning

confidence: 99%

New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

Ibrahim

Fouda

Elgammal

et al. 2022

Sci Rep

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“…[ 103 ] Some indole–thiadiazole hybrids also possessed a certain antibacterial activity, and among them, hybrids 47a,b showed remarkable antibiofilm activity against S. aureus with IC 50 values of 0.5 and 0.8 μg/ml, respectively, so both of them warrant further investigation. [ 104,105 ]…”

Section: Indole/isatin–azole Hybridsmentioning

confidence: 99%

Indole/isatin‐containing hybrids as potential antibacterial agents

Song

Bian

et al. 2020

Archiv der Pharmazie

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The emergence and worldwide spread of drug-resistant bacteria have already posed a serious threat to human life, creating the urgent need to develop potent and novel antibacterial drug candidates with high efficacy. Indole and isatin (indole-2,3-dione) present a wide structural and mechanistic diversity, so their derivatives possess various pharmacological properties and occupy a salient place in the development of new drugs. Indole/isatin-containing hybrids, which demonstrate a promising activity against a panel of clinically important Gram-positive and Gram-negative bacteria, are privileged scaffolds for the discovery of novel antibacterial candidates. This review, covering articles published between January 2015 and May 2020, focuses on the development and structure-activity relationship (SAR) of indole/isatincontaining hybrids with potential application for fighting bacterial infections, to facilitate further rational design of novel drug candidates.

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“…1D), the representative agrochemicals containing the 1,3,4-thiadiazole group, were widely used to control bacterial diseases in crops. In addition, researchers found that the 1,3,4-thiadiazole derivatives bearing sulfides moiety could effectively inhibit various agricultural bacteria (Wan et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group

Yan

et al. 2019

PeerJ

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A series of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group was designed and synthesized. The structures of all the compounds were well characterized using 1H NMR, 13C NMR and high-resolution mass spectrometer, and further confirmed by the X-ray diffraction analysis of 8d. The antimicrobial activities of all the target compounds against Xanthomonas oryzae pv. oryzicola, X. oryzae pv. oryzae, Rhizoctonia solani and Fusarium graminearum were evaluated. The in vitro antimicrobial bioassays indicated that some title compounds exhibited noteworthy antimicrobial effects against the above strains. Notably, the compound N-(5-(ethylthio)-1,3,4-thiadiazol-2-yl)-2-(5-methyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acetamide (8a) displayed obvious antibacterial effects against X. oryzae pv. oryzicola and X. oryzae pv. oryzae at 100 μg/mL with the inhibition rates of 30% and 56%, respectively, which was better than the commercial bactericide thiodiazole-copper. In addition, the anti-R. solani EC50 value of 8a was 33.70 μg/mL, which was more effective than that of the commercial fungicide hymexazol (67.10 μg/mL). It was found that the substitutes in the 1,3,5-thiadiazine-2-thione and the 1,3,4-thiadiazole rings played a vital role in the antimicrobial activities of the title compounds. More active title compounds against phytopathogenic microorganisms might be obtained via further structural modification.

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Design, synthesis and anti-bacterial evaluation of novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety

Cited by 7 publications

References 29 publications

New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

New thiadiazole modified chitosan derivative to control the growth of human pathogenic microbes and cancer cell lines

Indole/isatin‐containing hybrids as potential antibacterial agents

Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group

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