Thiazole-Based Thiazolidinones as Potent Antimicrobial Agents. Design, Synthesis and Biological Evaluation

Haroun, Michelyne; Tratrat, Christophe; Tsolaki, Evangelia; Geronikaki, Athina

doi:10.2174/1386207319666151203002348

Cited by 33 publications

(12 citation statements)

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“…Several other studies concluded that C-2 substitution with aryl ring is an important part of designing effective antibacterial compounds [83]. Furthermore, the presence of a substituted arylidine ring at the C-5 position always produces better inhibitors [88]. Certain effective steroidal based thiazolidinone derivatives have also been reported [89].…”

Section: -Thiazolidinones As Type III Secretion System Inhibitormentioning

confidence: 99%

Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications

Nirwan

Chahal

Kakkar

2019

Journal of Heterocyclic Chem

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Thiazolidinone is a biologically important five‐membered heterocyclic ring having almost all types of biological activities. This review covers various types of thiazolidinones, such as 2‐thiazolidinones, 4‐thiazolidinones, 5‐thiazolidinones, 2‐thioxo‐4‐thiazolidinones, and thiazolidiene‐2,4‐dione. The literature related to the physical properties, chemical reactions, and synthesis for these derivatives has been included. Recent advances in the biological activities reported for 4‐thiazolidinone derivatives, such as peroxisome proliferator‐activated receptor γ binders, follicle‐stimulating hormone agonists, cystic fibrosis transmembrane conductance regulator inhibitors, and antioxidants, have been covered in this review. Thus, this study may help in further optimizing these thiazolidinone derivatives as more effective drug agents.

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Section: -Thiazolidinones As Type III Secretion System Inhibitormentioning

confidence: 99%

Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications

Nirwan

Chahal

Kakkar

2019

Journal of Heterocyclic Chem

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“…The syntheses as well as the elemental and spectroscopic analyses of the titled compounds were performed according to previously published processes [ 17 – 19 ].…”

Section: Methodsmentioning

confidence: 99%

“…In our previous papers, we mentioned the synthesis [ 17 – 19 ] and the biological evaluation [ 18 ] of 5-arylidene-2-(6-methoxybenzothiazol-2-ylimino)-4-thiazolidinones. It has been established that these benzothiazole-based thiazolidinones significantly inhibited the growth of a broad spectrum of Gram-positive and Gram-negative bacteria as well as fungi.…”

Section: Introductionmentioning

confidence: 99%

Non-acidic bifunctional benzothiazole-based thiazolidinones with antimicrobial and aldose reductase inhibitory activity as a promising therapeutic strategy for sepsis

et al. 2021

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Sepsis is a life-threatening disease that affects millions of people worldwide. Microbial infections that lead to sepsis syndrome are associated with an increased production of inflammatory molecules. Aldose reductase has recently emerged as a molecular target that is involved in various inflammatory diseases, including sepsis. Herein, a series of previously synthesized benzothiazole-based thiazolidinones that exhibited strong antibacterial and antifungal activities has been evaluated for inhibition efficacy against aldose reductase and selectivity toward aldehyde reductase under in vitro conditions. The most promising inhibitor 5 was characterized with IC 50 value of 3.99 μM and a moderate selectivity. Molecular docking simulations revealed the binding mode of compounds at the active site of human aldose reductase. Moreover, owning to the absence of an acidic pharmacophore, good membrane permeation of the novel aldose reductase inhibitors was predicted. Excellent “drug-likeness” was assessed for most of the compounds by applying the criteria of Lipinski’s “rule of five”.

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“…Thiazole derivatives display a wide range of biological activities such as antimicrobial, anticancer and antidiabetic agents …”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Three Component One‐pot Synthesis of Bis(aminoazolo[1,5‐a]pyrimidines) and Bis(aminoazino[1,2‐a]benzimidazoles) Bearing Thiazole Moiety

2019

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Novel bis[(thiazol‐2‐yl)acetonitrile] derivatives were prepared in good yields by the cyclocondensation of bis(bromoacetyl) derivatives with two equivalents of 2‐cyanothioacetamide in dioxane at reflux. The bis[(thiazol‐2‐yl)acetonitrile] derivatives were taken as synthetic precursors for the synthesis of novel bis(aminoazolo[1,5‐a]pyrimidines), bearing thiazole moiety. The target molecules were prepared by the three component one pot reaction of bis[(thiazol‐2‐yl)acetonitrile] derivatives, dimethylformamide‐dimethylacetal and several of 3‐aminopyrazoles in pyridine under microwave irradiation at 140 °C for 2 h. Using the same protocol, novel bis(aminotriazolo[1,5‐a]pyrimidines), bis(aminopyrimido[1,2‐a]benzimidazoles) and bis(aminopyrido[1,2‐a]benzimidazoles), incorporating thiazole moieties, were prepared by using the appropriate heterocyclic amine or 2‐(1H‐benzoimidazol‐2‐yl)acetonitrile instead of 3‐aminopyrazoles. The structure of the newly prepared thiazoles was confirmed via considering their elemental analyses and spectral data.

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Thiazole-Based Thiazolidinones as Potent Antimicrobial Agents. Design, Synthesis and Biological Evaluation

Cited by 33 publications

References 0 publications

Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications

Thiazolidinones: Synthesis, Reactivity, and Their Biological Applications

Non-acidic bifunctional benzothiazole-based thiazolidinones with antimicrobial and aldose reductase inhibitory activity as a promising therapeutic strategy for sepsis

Microwave Assisted Three Component One‐pot Synthesis of Bis(aminoazolo[1,5‐a]pyrimidines) and Bis(aminoazino[1,2‐a]benzimidazoles) Bearing Thiazole Moiety

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