Synthesis, anti-hyperglycaemic activity, and in-silico studies of N-substituted 5-(furan-2-ylmethylene)thiazolidine-2,4-dione derivatives

Mahapatra, Manoj Kumar; Saini, Rajnish; Kumar, Manoj

doi:10.1007/s11164-016-2592-x

Cited by 7 publications

(2 citation statements)

References 18 publications

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“…For example, by reacting thiazolidine-2,4-diones with furan-2-carbaldehyde and alkyl halides, a series of N-substituted 5-(furan-2-ylmethylene)thiazolidine-2,4diones was prepared, that have antihyperglycemic activity. 17 From a synthetic chemistry point of view, the 4-oxo-3aryl/alkyl-2-(arylimino)thiazolidin-5-ylidene moiety has three electrophilic sites, of which the exocyclic C=C double bond acts as a dipolarophile in 1,3-dipolar cycloaddition reactions. Accordingly, Singh and co-workers reported a multicomponent 1,3-dipolar cycloaddition reaction for the synthesis of dispiro-thiazolidinoneoxindoles using (2Z)-methyl-2-((Z)-4-oxo-3-aryl-2-(arylimino)thiazolidin-5ylidene)acetates, substituted isatins and an -amino acid.…”

Section: Paper Synthesismentioning

confidence: 99%

Efficient Synthesis of (2Z,5Z)-3-Benzyl/alkyl-5-(2-oxo-5-aryl-3 (2H)-furanylidene)-2-(phenylimino)-1,3-thiazolidin-4-ones via a One-Pot Three-Component Reaction

Alizadeh,

Moterassed

2024

Synthesis

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A simple and efficient strategy for the chemoselective synthesis of (2Z,5Z)-3-benzyl/alkyl-5-(2-oxo-5-arylfuran-3(2H)-ylidene)-2-(phenylimino)thiazolidin-4-one derivatives is developed via a sequential three-component reaction of readily available phenacyl bromides, pyridine and methyl 2-(3-benzyl/alkyl-4-oxo-2-(phenylimino)thiazolidin-5-ylidene)acetates in acetonitrile at room temperature. The advantages of this one-pot sequential Michael addition/1,2-H shift/elimination of pyridine/intramolecular cyclization are highlighted by its low energy requirements (short reaction times at room temperature), excellent yields, the absence of a metal catalyst, and mild conditions. The product structures are characterized by spectroscopic techniques and single-crystal X-ray analysis.

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Section: Paper Synthesismentioning

confidence: 99%

Efficient Synthesis of (2Z,5Z)-3-Benzyl/alkyl-5-(2-oxo-5-aryl-3 (2H)-furanylidene)-2-(phenylimino)-1,3-thiazolidin-4-ones via a One-Pot Three-Component Reaction

Alizadeh,

Moterassed

2024

Synthesis

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“…10,11 Reports of anti-hyperglycaemic potential of various 5-arylidene TZD derivatives have been published from various laboratories. 10,[12][13][14][15][16][17][18] Various TZD containing PTP 1B inhibitors incorporated with weakly polar sulfonyl moiety (hydrogen bond acceptor) have revealed interactions with many binding site residues (Ala 217, Ile 221, Gln 262, Arg 254, Tyr 20, Arg 24, Arg 47, Asp 48 and Phe 182) of both catalytic as well as non-catalytic sites of PTP 1B enzyme. [19][20][21][22] Many substituted TZD derivatives have also been reported as aldose reductase inhibitors which have potential to treat type 2 diabetes and the related secondary complications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-hyperglycaemic Study of Aryl Sulfonate Ester Conjugated 5-arylidene-thiazolidine-2,4-diones

Mehta¹,

Mahapatra²

2021

IJPER

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Background: Diabetes mellitus, a lifestyle related global health crisis has rapidly engulfed the entire world. In the past, various thiazolidinedione derivatives have been successfully developed for management of diabetes. Materials and Methods: Herein, we report synthesis, characterization ( 1 H-NMR, 13 C-NMR and mass spectroscopy methods) of novel aryl sulfonyloxy-5-arylidene thiazolidine-2,4-dione analogues. Anti-hyperglycaemic action (Alloxan-induced method) was performed for evaluating the antidiabetic potential of the synthesized compounds. Docking analysis of the final compounds were carried out to reveal interactions with the active site pocket of enzymes like protein tyrosine phosphatase 1B, aldose reductase and peroxisome proliferator activated-γ. The synthesized compounds were further subjected to ADME (Absorption, Distribution, Metabolism, Elimination) prediction studies to prove their drug-like potential. Results: Compound 10 and 12 showed comparable reduction in blood sugar as that with pioglitazone. Docking studies helped in understanding the probable binding mode inside the binding cavity of the concerned receptors. Conclusion: Aryl sulfonate esters with phenyl and chloro phenyl substituents were found to have superior anti-hyperglycaemic activity.

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Syntheses, biological evaluation of some novel substituted benzoic acid derivatives bearing hydrazone as linker

et al. 2021

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Synthesis, anti-hyperglycaemic activity, and in-silico studies of N-substituted 5-(furan-2-ylmethylene)thiazolidine-2,4-dione derivatives

Cited by 7 publications

References 18 publications

Efficient Synthesis of (2Z,5Z)-3-Benzyl/alkyl-5-(2-oxo-5-aryl-3 (2H)-furanylidene)-2-(phenylimino)-1,3-thiazolidin-4-ones via a One-Pot Three-Component Reaction

Efficient Synthesis of (2Z,5Z)-3-Benzyl/alkyl-5-(2-oxo-5-aryl-3 (2H)-furanylidene)-2-(phenylimino)-1,3-thiazolidin-4-ones via a One-Pot Three-Component Reaction

Synthesis and Anti-hyperglycaemic Study of Aryl Sulfonate Ester Conjugated 5-arylidene-thiazolidine-2,4-diones

Syntheses, biological evaluation of some novel substituted benzoic acid derivatives bearing hydrazone as linker

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