Design, synthesis, antiproliferative and antimicrobial evaluation of a new class of disulfides containing 1,3,4-thiadiazole units

Zhang, Ruilian; Li, Bo; Chi, Chun-Lan; Liu, Yang; Liu, Xuguang; Li, Junjie; Li, Wei; Chen, Baoquan

doi:10.1007/s00044-022-02937-4

Cited by 7 publications

(4 citation statements)

References 38 publications

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“…Thiadiazoles, an azole derivative serves as a prominent intermediate in the synthesis of biologically active substances. Thiadiazole, a bioisosteric substitute of the thiazole moiety, features sulfur and nitrogen heteroatoms within its core nucleus, offering a range of isomers with pharmaceutical applications [26–33] …”

Section: Introductionmentioning

confidence: 99%

“…Thiadiazole, a bioisosteric substitute of the thiazole moiety, features sulfur and nitrogen heteroatoms within its core nucleus, offering a range of isomers with pharmaceutical applications. [26][27][28][29][30][31][32][33] Of specific importance is the 1,3,4-thiadiazole isomer (Figure 1), which holds significant therapeutic value. The pronounced aromaticity of the 1,3,4-thiadiazole nucleus confers in vivo stability to the ring and exhibits low toxicity in higher vertebrates, including humans.…”

Section: Introductionmentioning

confidence: 99%

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Anti‐Biofilm and Anti‐Virulence Potential of 2‐Amino‐1,3,4‐Thiadiazole Derivatives

Saravanan,

Venugopal,

Murugesan

et al. 2024

ChemistrySelect

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Biofilms are microbial communities that facilitate the pathogenesis of life‐threatening microbial infections through the glazing of mucosal surfaces or implanted devices thus protecting them from medications and increasing mortality rates. To discover a new class of antibiofilm agents 2‐amino‐1,3,4 thiadiazoles hybridized with pharmacologically active heterocycles were designed and synthesized. The compounds were characterized by infrared, nuclear magnetic resonance, mass spectroscopy and elemental analysis. All the compounds were assessed for their anti‐biofilm and anti‐virulence activity against P. aeruginosa and S. aureus. Quinoline‐substituted thiadiazoles were found to possess potent anti‐biofilm activity against P. aeruginosa and S. aureus. The molecular docking analysis further confirms the antibiofilm potential of the compounds. Density functional theory studies were carried out to investigate the electronic and molecular properties of the most active hybrids.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anti‐Biofilm and Anti‐Virulence Potential of 2‐Amino‐1,3,4‐Thiadiazole Derivatives

Saravanan,

Venugopal,

Murugesan

et al. 2024

ChemistrySelect

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“…Drug resistibility is one of the major problems occurring worldwide and to deal with this, the need of synthesizing new compounds has become one of the most interesting research areas. Thiadiazole nucleus is a well-known and one of the most important heterocyclic nuclei, exhibiting various biological activities, such as anti-microbial [1][2][3][4][5], anti-convulsant [6][7][8], anti-cancer [4,9,10], anti-viral [11,12], anti-tuberculosis [12,13], anti-inflammatory and analgesic [14][15][16], diuretic [17], anti-diabetic [18,19], anti-depressant [20,21], anti-ulcer [16,22], anti-malarial, anti-leishmanicidal [23,24], anti-influenza [25,26], anti-hypolipidemic, antihyperlipidemia [27,28], anti-hypertensive [29], etc. Thiadiazole is a five-membered heterocyclic ring containing a sulfur atom, two nitrogen atoms, and hydrogen binding domain.…”

Section: Introductionmentioning

confidence: 99%

Diverse Biological Activities of 1,3,4-Thiadiazole Scaffold

2022

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The chemistry of 1,3,4-thiadiazole is one of the most interesting scaffolds for synthesizing new drug molecules due to their numerous pharmacological activities. Several modifications in the thiadiazole ring have been made, proving it to be more potent and highly effective with a less toxic scaffold for various biological activities. There are several marketed drugs containing 1,3,4-thiadiazole ring in their structure. In this review article, we have tried to compile the newly synthesized 1,3,4-thiadiazole derivatives possessing important pharmaceutical significance since 2014.

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“…The biological activities of molecules containing triazole or thiadiazole are very diverse. Because of the variety of biological activities, 1,3,4 thiadiazole is one of the most beneficial isomeric forms. − The 1,3,4-thiadiazole structure is one of the most significant and well-known heterocycles, which is a common and complementary advantage of a range of pharmaceutical and natural substances. The thiadiazole ring is present as a key component in an assemblage of pharmacological categories because 1,3,4-thiadiazole derivatives have a wide range of biological activities, including antimicrobial, antiviral, anti-inflammatory, and analgesic, and anticancer activity …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, Dynamics, Quantum-Chemical Computation, and Antimicrobial Activity Studies of Some New Benzimidazole–Thiadiazole Hybrids

et al. 2022

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In this study, some new compounds, which are 2aminothiadiazole derivatives linked by a phenyl bridge to the 2position of the benzimidazole ring, were designed and synthesized as antimicrobial agents. The structures of the compounds were elucidated by 1 H and 13 C NMR spectroscopy, high-resolution mass spectrometry, and elemental analysis. The antifungal activities of the synthesized compounds were tested on Candida albicans, Candida krusei, Candida glabrata, and Candida parapsilosis. Compound 5f is more active against C. albicans and C. glabrata than standard fluconazole and varicanazole. Compounds were also evaluated for their counteracting activity against Gram-positive Escherichia coli, Serratia marcescens, Klebsiella pneumoniae, and Pseudomonas aeruginosa and Gram-negative Enterococcus faecalis, Bacillus subtilis, and Staphylococcus aureus. Compounds 5c and 5h had minimum inhibitory concentrations against E. faecalis close to that of the standard azithromycin. Molecular docking studies were performed against Candida species' 14-α demethylase enzyme. 5f was the most active compound against Candida species, which gave the highest docking interaction energy. The stabilities of compounds 5c and 5f with CYP51 were tested using 100 ns molecular dynamics simulations. According to the theoretical ADME calculations, the profiles of the compounds are suitable in terms of limiting rules. HOMO−LUMO analysis showed that 5h is chemically more reactive (represented with the lower ΔE = 3.432 eV) than the other molecules, which is compatible with the highest antibacterial activity result.

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Design, synthesis, antiproliferative and antimicrobial evaluation of a new class of disulfides containing 1,3,4-thiadiazole units

Cited by 7 publications

References 38 publications

Anti‐Biofilm and Anti‐Virulence Potential of 2‐Amino‐1,3,4‐Thiadiazole Derivatives

Anti‐Biofilm and Anti‐Virulence Potential of 2‐Amino‐1,3,4‐Thiadiazole Derivatives

Diverse Biological Activities of 1,3,4-Thiadiazole Scaffold

Synthesis, Molecular Docking, Dynamics, Quantum-Chemical Computation, and Antimicrobial Activity Studies of Some New Benzimidazole–Thiadiazole Hybrids

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