Thiazolidine-2,4-dione derivatives: Programmed chemical weapons for key protein targets of various pathological conditions

Chadha, Navriti; Bahia, Malkeet Singh; Kaur, Maninder

doi:10.1016/j.bmc.2015.03.071

Cited by 90 publications

(55 citation statements)

References 142 publications

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“…Heterocyclic compounds containing nitrogen, oxygen, and sulfur atoms are known for exhibiting a wide spectrum of pharmacological activities. [1][2][3][4][5] Since the anticonvulsant, antimicrobial, and antihyperglycemic potential of several thiazolidine-2,4-dione-bearing compounds was reported, this moiety has been intensively studied in the last decades. 3 Thiazolidine-2,4-dione derivatives have been also identified as potential inhibitors of lanosterol 14α-demethylase.…”

Section: Introductionmentioning

confidence: 99%

3,5-Disubstituted Thiazolidine-2,4-Diones: Design, Microwave-Assisted Synthesis, Antifungal Activity, and ADMET Screening

et al. 2018

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A series of 12 new thiazolidine-2,4-dione derivatives were obtained by microwave-assisted synthesis. All compounds were physicochemically characterized by quantitative elemental C, H, N, S analysis and spectral data (mass spectrometry [MS], infrared [IR], and nuclear magnetic resonance [NMR]), with the results being in agreement with the expected data. An in vitro screening performed on Candida albicans ATCC 10231 showed their moderate antifungal activity, which was further investigated by determining the minimum inhibitory concentration and minimum fungicidal concentration values for the most active compounds on four strains of Candida. The molecular docking studies, performed against a fungal lanosterol 14α-demethylase, emphasized the importance of different molecular fragments in the compounds' structures for their antifungal activity. The synthesized compounds were subjected to in silico screening for the prediction of their absorption, distribution, metabolism, excretion, and toxicity (ADMET) and molecular properties. The results of the antifungal activity assays, docking study, and ADMET predictions revealed that the synthesized compounds are potential anti- Candida agents that might act by interacting with the fungal lanosterol 14α-demethylase and could be further optimized and developed as antifungal agents.

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Section: Introductionmentioning

confidence: 99%

3,5-Disubstituted Thiazolidine-2,4-Diones: Design, Microwave-Assisted Synthesis, Antifungal Activity, and ADMET Screening

et al. 2018

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“…[8][9] Thiazolidine-2,4-dione are a class of heterocyclic ring system and plays an important role in different areas of medicinal chemistry. 10 As discussed earlier, TZDs act as PPARγ agonists by playing a role in insulin sensitization and also promoting glucose utilization in peripheral tissues. The history of TZDs came into the picture by the discovery of Ciglitazone in early 1982.…”

Section: Introductionmentioning

confidence: 93%

Comparative Design, In Silico Dockingand Predictive ADME/ TOX Properties of Some Novel 2, 4-hydroxy Derivatives of Thiazolidine-2, 4-diones as PPARÎ³ Modulator

et al. 2017

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Peroxisome proliferated receptors (PPARs) are important targets for drugs used in the treatment of various metabolic disorders. We have reported 4-hydroxy benzylidene derivatives of thiazolidine-2,4-diones with reversed orientation in the active site of PPARγin our earlier communication. With the reversed conformation of TZD, fitting the established pharmacophore was discussed. The current simulation studies revolves around the 2,4-dihydroxy benzylidene derivatives expecting H-bonding interactions similar to Rosiglitazone's acidic head. The docking protocol was validated by enrichment studies using decoys and actives from DUD. Designed compounds were showing interactions similar to the actives in the top 10%, 5% and 1%. They also exhibited H-bonding interactions similar to their monohydroxy counterparts without any additional H-bonding interactions due to introduction of additional hydroxy functional groups. Predicted ADMET report reveals that 5 molecules show favourable hERG-I and -II properties and nine compounds show best metabolic stability.

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“…The underlying goal for research into medicinal chemistry is to discover new products with greater biological activity, achieving a low number of by-products during the synthesis and low toxicity of both the intermediates and the final products. Accordingly, considerable attention has been devoted to thiazolidinedione derivatives (TZDs), both from a synthetic point of view and biological applications [1][2][3][4][5][6]. In this regard, TZDs have been used as the following: antibacterial and antifungal agents [7][8][9][10][11][12]; anti-inflammatory drugs [13][14][15][16]; aldose reductase inhibitors [17,18]; and anticancer [19][20][21][22][23][24][25], antiplasmodial inhibitors [26], and antidiabetic agents [27][28][29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of a New Series of Thiazolidine-2,4-diones Carboxamide and Amino Acid Derivatives

et al. 2019

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Novel thiazolidine-2,4-dione carboxamide and amino acid derivatives were synthesized in excellent yield using OxymaPure/N,N′-diisopropylcarbodimide coupling methodology and were characterized by chromatographic and spectrometric methods, and elemental analysis. The antimicrobial and antifungal activity of these derivatives was evaluated against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), two-Gram negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and one fungal isolate (Candida albicans). Interestingly, several samples demonstrated weak to moderate antibacterial activity against Gram-negative bacteria, as well as antifungal activity. However, only one compound namely, 2-(5-(3-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetic acid, showed antibacterial activity against Gram-positive bacteria, particularly S. aureus.

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Thiazolidine-2,4-dione derivatives: Programmed chemical weapons for key protein targets of various pathological conditions

Cited by 90 publications

References 142 publications

3,5-Disubstituted Thiazolidine-2,4-Diones: Design, Microwave-Assisted Synthesis, Antifungal Activity, and ADMET Screening

3,5-Disubstituted Thiazolidine-2,4-Diones: Design, Microwave-Assisted Synthesis, Antifungal Activity, and ADMET Screening

Comparative Design, In Silico Dockingand Predictive ADME/ TOX Properties of Some Novel 2, 4-hydroxy Derivatives of Thiazolidine-2, 4-diones as PPARÎ³ Modulator

Synthesis and Antimicrobial Activity of a New Series of Thiazolidine-2,4-diones Carboxamide and Amino Acid Derivatives

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