1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents

Othman, Adil A.; Mebrouk, Kihel; Amara, Sarah

doi:10.1016/j.arabjc.2014.09.003

Cited by 79 publications

(62 citation statements)

References 46 publications

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“…The chemical used in the present study was procured from Sigma Aldrich (USA). The spectra of 1 H NMR and 13 C NMR were recorded on Bruker Avance 400 and…”

Section: Methodsmentioning

confidence: 99%

“…Thiadiazole is a well-known pharmacophore endowed with diverse pharmacological activities such as antibacterial [13,14], antifungal [15], anticancer [16], antimalarial [17], and anti antidiabetic [18]. On the contrary, pyrazole is also reported to be present in many active pharmaceutical agents displaying myriad activities such as antioxidant [19,20], antimycobacterial [21], antiviral [22,23], anticonvulsant [24], and antibacterial [25].…”

Section: Introductionmentioning

confidence: 99%

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Design and Development of Novel Pyrazole-Thiadiazole Derivatives as NF-ĸB Inhibitor and Cardioprotective Effect against Isoproterenol Induced Myocardial Infarction in Sprague-Dawley Rats

Wang¹,

Guo²,

Wu³

et al. 2020

Pharmacology

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The present study was aimed to discover novel pyrazole-thiadiazole derivatives as potent NF-ĸB inhibitor and its cardioprotective effect against isoproterenol (ISO)-induced myocardial infarction (MI) in rats. The designed analogues showed potent inhibition of NF-κB transcriptional activity in luciferase assay. Among the tested derivatives, compound 6c revealed as a potent inhibitor of NF-κB. It has been found that 6c exerts protective effect via multiple mechanisms against MI, such as the levels of various cardiac injury biomarkers (creatine kinase, creatine kinase myocardial band, aminotransferase, alanine aminotransferase and lactate dehydrogenase) were found to be decreased after 6c administration as compared to ISO group. The effect of 6c was also investigated on oxidative stress via quantifying the level of various biomarkers (MDA, MPO, superoxide dismutase, and glutathione peroxidase-1). In histopathology analysis, 6c showed restoration of microstructural changes in cardiac tissues as compared to the ISO-treated group. The groups treated by 6c groups showed dose-dependent significant reduction of cell count in TUNEL analysis. In Western blot analysis, 6c causes significant modulation of Bcl2 family proteins and inhibition of phosphorylation of NF-κB and IκBα. It could be suggested that 6c exerts protective action against MI via modulation of apoptosis and oxidative stress, Bcl-2 genes, and NF-κB.

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“…The chemical used in the present study was procured from Sigma Aldrich (USA). The spectra of 1 H NMR and 13 C NMR were recorded on Bruker Avance 400 and…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design and Development of Novel Pyrazole-Thiadiazole Derivatives as NF-ĸB Inhibitor and Cardioprotective Effect against Isoproterenol Induced Myocardial Infarction in Sprague-Dawley Rats

Wang¹,

Guo²,

Wu³

et al. 2020

Pharmacology

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“…So, this is continuity in the path of a series of molecules already synthesized. At the same time, the selected 1,3,4-oxadiazole and 1,2,4-triazole derivatives are scaffolds that have a variety of biological importance widely reported in the literature (Othman et al, 2014). Thus, we propose to design and study theoretically twelve nucleoside analogues derived from D-glucaric acid (1), then to compare them to their precursor and its mono-lactones (2 and 3) taken as reference.…”

Section: Introductionmentioning

confidence: 99%

DFT Studies of New Class of Single-Headed Nucleosides Derived from the D-glucaric Acid

Amara¹

2020

SJKFU

Self Cite

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The nucleoside analogues can be conveniently classified into cyclic or acyclic analogues. The goal of this study is to anticipate the structural and electronic properties of new single-headed acyclo-C-nucleosides derived from the D-glucaric acid which are able to be in equilibrium with their corresponding cyclic forms by lactonization. The heterocyclic moieties selected for this study are: the 1,3,4-oxadiazole-2-thione, the 1,2,4-triazole-3-thiol and the 4-amino-1,2,4-triazole-3-thiol. Using density functional theory, the candidate nucleosides will be compared with the D-glucaric acid and its mono-lactones that are used as references. The results indicated that incorporating of the heterocycles significantly increase the reactivity of the new nucleosides. For the cyclic forms, a high reactivity of the molecules carrying the 6,3-lactone ring are observed in comparison with those carrying the 1,4-lactone ring. Whereas for the acyclic forms, the substitution of the carboxylic acid group by the heterocyclic moiety in position of carbon C6 gives a greater stability to the molecules compared with the same substitution in position C1. The results motivate theoretically the synthesis of this new class of nucleoside analogues, but it remains to find out the experimental conditions.

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“…1,3,4-Oxadiazole moieties display an inclusive variety of biological and pharmacological activities, for example, anti-cancer, anti-oxidant, anti-tubercular [4][5][6] . Besides anti-bacterial and anti-fungal properties, they have other biological properties such as anticonvulsant, anti-inflammatory and anti-anxiety 7,8 . Sulfonamides, antimicrobial agents, are synthetically formed from sulfanilic acid [9][10][11] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral Analysis and Antibacterial Evaluation of 5-Substituted-1,3,4-Oxadiazol-2-Yl 4-(4-Methylpiperidin-1-Ylsulfonyl)benzyl Sulfides

Aziz-Ur-Rehman

Ahtzaz

Abbasi

et al. 2017

J. Chil. Chem. Soc.

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Owing to valuable biological activities of 1,3,4-oxadiazole, sulfamoyl and piperidine functionalities, some new 1-(4-{[(5-substituted-1,3,4-oxadiazol-2-yl) thio]methyl}benzene sulfonyl)-4-methylpiperidine (6a-o) derivatives have been introduced. The target molecules were synthesized from different aralkyl/aryl carboxylic acids, 1a-o, through a series of steps. First the compounds, 1a-o, were converted to heterocyclic 1,3,4-oxadiazole nucleophiles, 4a-o. Second an electrophile as 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine (5) was synthesized from 4-methylpiperidine. Finally the target compounds, 6a-o, were prepared by reacting 4a-o with 5 in DMF and LiH. The final compounds were structurally elucidated by spectral data of IR, 1 H-NMR and EI-MS. All the compounds were screened for their antibacterial evaluation and found to exhibit valuable results.

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1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents

Cited by 79 publications

References 46 publications

Design and Development of Novel Pyrazole-Thiadiazole Derivatives as NF-ĸB Inhibitor and Cardioprotective Effect against Isoproterenol Induced Myocardial Infarction in Sprague-Dawley Rats

Design and Development of Novel Pyrazole-Thiadiazole Derivatives as NF-ĸB Inhibitor and Cardioprotective Effect against Isoproterenol Induced Myocardial Infarction in Sprague-Dawley Rats

DFT Studies of New Class of Single-Headed Nucleosides Derived from the D-glucaric Acid

Synthesis, Spectral Analysis and Antibacterial Evaluation of 5-Substituted-1,3,4-Oxadiazol-2-Yl 4-(4-Methylpiperidin-1-Ylsulfonyl)benzyl Sulfides

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