Green synthesis, antibacterial and antifungal evaluation of new thiazolidine-2,4-dione derivatives: molecular dynamic simulation, POM study and identification of antitumor pharmacophore sites

Ahmed, Sumeer; Bhat, Ajmal R.; Rahiman, Aziz Kalilur; Dongre, Rajendra S.; Hasan, Aso Hameed; Niranjan, Vidya; C, Lavanya; Sheikh, S. A.; Jamalis, Joazaizulfazli; Berredjem, Malika; Kawsar, Sarkar M. A.

doi:10.1080/07391102.2023.2258404

Cited by 9 publications

(1 citation statement)

References 76 publications

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“…5 TZDs reduce both fasting and postprandial hyperglycemia by reducing insulin resistance and enhancing the efficiency of endogenous insulin. TZDs possess a proven range of diversified therapeutic potentials, such as antidiabetic, 6 analgesic, anti-inflammatory, 7,8 wound healing, 9 antimalarial, 10 hypolipidemic, 11 antiproliferative, 12-14 antitubercular, 15,16 antimicrobial, 17 antiviral, 18 antifungal, [19][20][21] anticonvulsant, 22 and antioxidant 23,24 activities. Owing to the significant biological activity of thiazolidine-2,4-dione derivatives, much attention has been paid to the modification of the thiazole ring, which leads to the N-arylation of 2,4-thiazolidinediones with aryl halides, as a new synthetic procedure.…”

Section: Introductionmentioning

confidence: 99%

A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K₂CO₃ in DMF

Patil,

Khiratkar,

Ahmed

et al. 2024

React. Chem. Eng.

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Section: Introductionmentioning

confidence: 99%

A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K₂CO₃ in DMF

Patil,

Khiratkar,

Ahmed

et al. 2024

React. Chem. Eng.

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Synthesis, Characterization, Bioactivity Evaluation, and POM/DFT/Docking Analysis of Novel Thiazolidine Derivatives as Potent Anticancer and Antifungal Agents

Majed,

Abdalzahra,

Al‐Hujaj

et al. 2024

ChemistrySelect

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A series of 2,2′‐(1,4‐phenylene)bis(N‐substituted phenylthiazolidine‐4‐amide) derivatives, denoted as (A3–9), were synthesized, and characterized for their potential applications against prostate cancer cells (PC3), and Candida albicans fungi. These compounds incorporate various substituents on the phenyl ring such as 4‐NO2, 3‐NO2, 4‐COCH3, 4‐H, 4‐OCH3, 4‐OCH2CH3, and 4‐Cl. The chemical structures of these derivatives were confirmed by NMR, FTIR, and mass spectroscopy. Biological assays, utilizing the MTT assay for prostate cancer cells (PC3) and the disk diffusion assay for Candida albicans fungi, were conducted to evaluate the bioactivity of these compounds. The results revealed promising cytotoxic and antifungal activities. Specifically, compounds A3 (IC50=69.74±0.96), A4 (IC50=63.64±0.950), and A9 (IC50=57.14±0.88 μg/mL) exhibited notable potency against PC3 cells, while A7 and A8 exhibited considerable antifungal efficacy against Candida albicans with MIC of 312 μg/mL. Moreover, density functional theory (DFT) simulations were used to study electronic properties and reactivity descriptors such as energy gap (Eg), ionization potential (IP), electron affinity (EA), chemical potential (μ), chemical hardness (η), global softness (σ), electronegativity (χ), and electrophilicity (ω) to gain a better understanding of the Structure‐Activity Relationship (SAR). Molecular docking analysis against DNA Gyrase and EGFR tyrosine kinase enzymes revealed strong binding interactions of the investigated molecules within their active sites, making them valuable candidates for further development as therapeutic agents against prostate cancer and fungal infections. POM analysis indicates the presence of two antifungal pharmacophore sites (O1δ−, O2δ−) and (O3δ−, O4δ−), as well as two antitumor pharmacophore sites (O1δ−, NH1δ+) and (O4δ−, NH2δ+).

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Larvicidal activity, molecular docking, and molecular dynamics studies of 7-(trifluoromethyl)indolizine derivatives against Anopheles arabiensis

Singh,

Tiwari,

Deb

et al. 2024

Mol Divers

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Green synthesis, antibacterial and antifungal evaluation of new thiazolidine-2,4-dione derivatives: molecular dynamic simulation, POM study and identification of antitumor pharmacophore sites

Cited by 9 publications

References 76 publications

A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K₂CO₃ in DMF

A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K₂CO₃ in DMF

Synthesis, Characterization, Bioactivity Evaluation, and POM/DFT/Docking Analysis of Novel Thiazolidine Derivatives as Potent Anticancer and Antifungal Agents

Larvicidal activity, molecular docking, and molecular dynamics studies of 7-(trifluoromethyl)indolizine derivatives against Anopheles arabiensis

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Green synthesis, antibacterial and antifungal evaluation of new thiazolidine-2,4-dione derivatives: molecular dynamic simulation, POM study and identification of antitumor pharmacophore sites

Cited by 9 publications

References 76 publications

A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K2CO3 in DMF

A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K2CO3 in DMF

Synthesis, Characterization, Bioactivity Evaluation, and POM/DFT/Docking Analysis of Novel Thiazolidine Derivatives as Potent Anticancer and Antifungal Agents

Larvicidal activity, molecular docking, and molecular dynamics studies of 7-(trifluoromethyl)indolizine derivatives against Anopheles arabiensis

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A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K₂CO₃ in DMF

A safe and new strategy for N-arylation of 2,4-thiazolidinediones via microwave irradiation using base catalyst K₂CO₃ in DMF