Synthesis and Evaluation of N-Substituted Thiazolidine-2,4-dione Containing Pyrazole as a Potent Antimicrobial Agents

Desai, Nisheet C.; Satodiya, H. M.; Rajpara, K. M.; Joshi, V. V.; Bhatt, Kandarp; Vaghani, H. V.

doi:10.2174/22113525113119990117

Cited by 24 publications

(37 citation statements)

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“…The same findings are suitable for 2,4-thiazolidinedione derivatives e N3 modification provides to 5e40 folds increasing of the antimicrobial activity (72) [200,201].…”

Section: Antimicrobial Agentssupporting

confidence: 58%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

145

133

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The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

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“…The same findings are suitable for 2,4-thiazolidinedione derivatives e N3 modification provides to 5e40 folds increasing of the antimicrobial activity (72) [200,201].…”

Section: Antimicrobial Agentssupporting

confidence: 58%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

145

133

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“…Equimolar quantities of substituted pyrazole carbaldehydes ( 4a–o ) and TZD (earlier prepared from thiourea and chloroacetic acid) in absolute ethanol with few drops of glacial acetic acid and piperidine was refluxed for 2–3 h. The solvent was removed under reduced pressure; residue left behind was poured in crushed ice, filtered, washed with ice cold water, dried, and recrystallized from ethanol to yield the final derivatives (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Synthesis, docking, in vitro and in vivo antidiabetic activity of pyrazole‐based 2,4‐thiazolidinedione derivatives as PPAR‐γ modulators

Naim

Alam

et al. 2018

Archiv der Pharmazie

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The design, synthesis, structure-activity relationship, and biological activity of 2,4-thiazolidinedione derivatives as peroxisome proliferator-activated receptor-γ (PPAR-γ) modulators for antidiabetic activity are reported. Fifteen 2,4-thiazolidinedione derivatives clubbed with pyrazole moiety were docked into the ligand binding domain of PPAR-γ by the Glide XP module of Schrodinger. Eight derivatives (5a, 5b, 5d, 5f, 5i, 5l, 5n, 5o) having Glide XP scores > -8 as compared to the standard drug, rosiglitazone (Glide XP score = -9.165), showed almost similar interaction with the amino acids such as HIS 449, TYR 473, TYR 327, HIS 323, and SER 289 in the molecular docking studies. These eight derivatives were further screened for PPAR-γ transactivation and in vivo blood glucose lowering activity in the streptozotocin-induced diabetic rat model. Compounds 5o, 5n, 5a, 5i, and 5b showed 52.06, 51.30, 48.65, 43.13, and 40.36% PPAR-γ transactivation as compared to the reference drugs rosiglitazone and pioglitazone with 85.30 and 65.22% transactivation, respectively. The data analysis showed significant blood glucose lowering effects (hypoglycemia) of compounds 5o, 5n, and 5a (140.1 ± 4.36, 141.4 ± 6.15, and 150.7 ± 4.15, respectively), along with reference drugs pioglitazone (135.2 ± 4.91) and rosiglitazone (141.1 ± 5.88) as compared to the diabetic control. Furthermore, the most potent compound 5o also elevated the PPAR-γ gene expression by 2.35-fold as compared to rosiglitazone (1.27-fold) and pioglitazone (1.6-fold). It also significantly lowered the AST, ALT, and ALP levels and caused no damage to the liver.

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“…The synthesis of TZD derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were accomplished using the synthetic route depicted in Scheme 1. At first, 2-chloroacetic acid was treated with thiourea in conc.…”

Section: Chemistrymentioning

confidence: 99%

“…Further, the reaction of (I) with terephthalaldehyde yielded 4-((2,4-dioxothiazolidin-5-ylidene) methyl) benzaldehyde (II). Intermediate-II on further treatment with substituted anilines/amines yielded final 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). The physicochemical characterization and spectral analysis of the synthesized derivatives are given in Table 1.The molecular structures of the synthesized derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were established using elemental analysis and spectral studies [FT-IR (KBr, cm -1 ), 1…”

Section: Chemistrymentioning

confidence: 99%

“…Small heterocyclic rings having sulfur and nitrogen atoms like 4 thiazolidine-2,4-dione (TZD) have been under study for a long time due to their synthetic variety and therapeutic relevance [4]. The TZD moiety is reported to possess extensive biological potential such as antifungal [5], analgesic, anti-inflammatory [6], hypoglycemic [7], antimalarial [8], antiproliferative [9], antitubercular [10], antioxidant [11], antiviral [12], hypolipidemic [13] and antibacterial [14][15][16] etc. The biological potential of TZD moiety is displayed in Fig.…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives

Kumar

Deep

Marwaha

2020

Preprint

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Background: Looking at the extensive range of biological potential of thiazolidine-2,4-dione (TZD) moiety, a new series of thiazolidine-2,4-dione analogues was synthesized. Different spectral techniques (1H-NMR, IR, MS etc.) were used to confirm the chemical structures of the synthesized analogues. These synthesized compounds were then screened for their antioxidant and antimicrobial potential.Results and discussion: The antimicrobial screening was carried out against selected strains of fungi and bacteria using serial tube dilution method. The antioxidant potential was assessed using stable 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. Further, the interaction between synthesized thiazolidine-2,4-dione compounds and DNA gyrase was explored using molecular docking studies. Various ADME parameters were also studied to evaluate the drug likeness of the synthesized compounds. Conclusion: In antimicrobial evaluation, the compounds 4, 9, 11, 12, 13, 15 and 16 displayed promising activity against selected strains of microbes. Antioxidant evaluation found compound 6 having IC50 = 9.18 μg/mL to be the most potent compound in the series. The molecular docking study revealed compounds 4 (dock score = -4.73) and 7 (dock score = -4.61) with decent docking score possess good interaction inside the ATP binding pocket and therefore can be used as lead structure for further optimizing into potent antimicrobial molecule.

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Synthesis and Evaluation of N-Substituted Thiazolidine-2,4-dione Containing Pyrazole as a Potent Antimicrobial Agents

Cited by 24 publications

References 0 publications

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Synthesis, docking, in vitro and in vivo antidiabetic activity of pyrazole‐based 2,4‐thiazolidinedione derivatives as PPAR‐γ modulators

Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives

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