Microwave induced synthesis of the thiazolidine‐2,4‐dione motif and the efficient solvent free‐solid phase parallel syntheses of 5‐benzylidene‐thiazolidine‐2,4‐dione and 5‐benzylidene‐2‐thioxo‐thiazolidine‐4‐one compounds

Kumar, B. R. Prashantha; Nanjan, M. J.; Suresh, B.; Karvekar, M. D.; Adhikary, Laxmi

doi:10.1002/jhet.5570430413

Cited by 46 publications

(10 citation statements)

References 16 publications

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“…Next an S N Ar reaction on 2-fluoropyridine ( 1.66 ) followed by oxidation of the benzylic alcohol using immobilised chromium(VI) oxide yielded the aldehyde 1.67 required for the previously described Knoevenagel condensation. The five membered heterocycle 2,4-thiazolidinedione ( 1.68 ) is readily available commercially, but can be easily prepared at scale via a simple cyclocondensation between thiourea and chloroacetic acid [42]. Finally, hydrogenation of the double bond using Pearlmans catalyst furnishes rosiglitazone ( 1.40 ).…”

Section: Reviewmentioning

confidence: 99%

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

Baumann¹,

Baxendale²

2013

Beilstein J. Org. Chem.

699

336

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This review which is the second in this series summarises the most common synthetic routes as applied to the preparation of many modern pharmaceutical compounds categorised as containing a six-membered heterocyclic ring. The reported examples are based on the top retailing drug molecules combining synthetic information from both scientific journals and the wider patent literature. It is hoped that this compilation, in combination with the previously published review on five-membered rings, will form a comprehensive foundation and reference source for individuals interested in medicinal, synthetic and preparative chemistry. 2265

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Section: Reviewmentioning

confidence: 99%

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

Baumann¹,

Baxendale²

2013

Beilstein J. Org. Chem.

699

336

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“…2,4-Dioxothiazolidine acid derivatives were prepared in three steps following the reported method [35,40]. A solution of previously prepared TZD 1 was treated with various appropriate aldehydes via refluxing in ethanol for 24 h in the presence of piperidine as a catalyst.…”

Section: General Procedures For the Synthesis Of 24-dioxothiazolidinementioning

confidence: 99%

“…2-(5-Arylidene-2,4-dioxothiazolidine-3-yl)acetic acids 3a-g were synthesized as outlined in Scheme 1, where TZD 1 was prepared following the reported strategy [35] with minor modifications. TZD solution was treated with various appropriate aldehydes via refluxing in ethanol for 24 h in the presence of piperidine as a catalyst to afford compounds 2a-g.…”

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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“…Formed product was filtered and washed with water to remove the trace of HCl and kept for drying. Recrystallization was done using ethanol 19…”

Section: Synthesis Of 24-thiazolidinedione (3)mentioning

confidence: 99%

Microwave Assisted Synthesis, Qsar and Molecular Docking Studies of 2,4- Thiazolidinedione Derivatives

Geetha¹,

Swarnalatha²,

Reddy³

2019

RJC

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Synthetic organic chemistry involves selection and optimization of lead, synthesis and characterization of work for practical purposes. A series of new thiazolidinedione derivatives have been designed and synthesized through microwave-assisted technique. The synthesized compounds were screened by Insilco methods like molecular docking, QSAR studies in order to explore the anti-diabetic activity, synthetic assessability of compounds against the peroxisome proliferator-activated the receptor (PPARγ). Compounds which showed higher glide score than standard (Pioglitazone) were synthesized using the microwave. Compounds were characterized with the help of FT-Infrared spectroscopy, Proton NMR, C-13 NMR spectroscopic studies and Lc-Ms.

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Microwave induced synthesis of the thiazolidine‐2,4‐dione motif and the efficient solvent free‐solid phase parallel syntheses of 5‐benzylidene‐thiazolidine‐2,4‐dione and 5‐benzylidene‐2‐thioxo‐thiazolidine‐4‐one compounds

Cited by 46 publications

References 16 publications

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

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

Microwave Assisted Synthesis, Qsar and Molecular Docking Studies of 2,4- Thiazolidinedione Derivatives

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