Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds

Koppireddi, Satish; Komsani, Jayaram Reddy; Avula, Sreenivas; Sujitha, Pombala; Vasamsetti, Satishbabu; Kotamraju, Srigiridhar; Yadla, R.

doi:10.1016/j.ejmech.2013.06.005

Cited by 60 publications

(29 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thiazolidine-2,4-dione scaffold compounds are considered to be an important class of heterocycles due to their diverse biological activities. They have been reported to exhibit anti-cancer (Ashok & Vanaja, 2016;Wei et al, 2009;Xia et al, 2009), anti-plasmodial inhibitor (Sharma et al, 2015), anti-leishmanial (Leite et al, 2016), anti-inflammatory (Barros et al, 2010), anti-microbial (Liu et al, 2011), anti-oxidant and anti-hyperglycemic activities (Koppireddi et al, 2013;Oakes et al, 1994). In this context, we report herein the synthesis and crystal structure of the title compound.…”

Section: Structure Descriptionmentioning

confidence: 89%

(5Z)-3-(2-Oxopropyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione

et al. 2016

View full text Add to dashboard Cite

In the crystal of the title molecule, C16H17NO6S, there are three sets of intermolecular C—H...O hydrogen bonds, as well as two sets of intermolecular C—H...π(ring) interactions. In addition, the thiazolidene rings participate in offset π–π stacking interactions [centroid–centroid distance = 3.685 (1) Å]. These generate small channels running parallel to theaaxis with approximate cross-sections of 3.7 × 8.1 Å.

show abstract

Section: Structure Descriptionmentioning

confidence: 89%

(5Z)-3-(2-Oxopropyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The antioxidant evaluation of synthesized thiazolidine-2,4-dione derivatives was determined using stable 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging model [29]. The diluted solution of synthesized compounds in methanol of 25 μg/mL, 50 μg/mL, 75 μg/ mL and 100 μg/mL were prepared and equal amount of methanolic solution of DPPH (0.0039%) was added followed by vigorous shaking.…”

Section: In Vitro Antioxidant Assaymentioning

confidence: 99%

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

2020

View full text Add to dashboard Cite

Background: Looking at the extensive biological potential of thiazolidine-2,4-dione (TZD) moiety, a new series of thiazolidine-2,4-dione analogues was synthesized. Different spectral techniques (1 H-NMR, IR, MS etc.) were used to confirm the chemical structures of the synthesized analogues. These synthesized compounds were 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 IC 50 = 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 of DNA gyrase and therefore can be used as lead structure for further optimizing into potent antimicrobial molecule.

show abstract

“…), TMEDA (10 mol%), CuA C H T U N G T R E N N U N G (NO 3 ) 2 ·3 H 2 O (0.8 mol%) and H 2 O (1 mL) was stirred 4 h in air at ambient temperature. Then the reaction was stopped and the mixture was extracted with ethyl acetate (3 10 mL), the organic layer was washed with water (2 10 mL), then dried over anhydrous Na 2 SO 4 and evaporated under vacuum. The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate as an eluent to give the corresponding products 3a-3q.…”

Section: Typical Experimental Procedures For Copper/ Tmeda-catalyzed Tmentioning

confidence: 99%

Copper/N,N,N′,N′‐Tetramethylethylenediamine‐Catalyzed Synthesis of N‐Substituted Benzoheterocycles via CS Cross‐ Coupling at Ambient Temperature in Water

et al. 2014

View full text Add to dashboard Cite

Copper/N,N,N',N'-tetramethylethylenedi-A C H T U N G T R E N N U N G amine (Cu/TMEDA)-catalyzed ambient temperature tandem reactions of isothiocyanates with 2-iodophenols or 2-iodoanilines in water without the protection of an inert atmosphere are described, which provide a simple, rapid, environmental method for the synthesis of a variety of 2-iminobenzo-1, 3-oxathioles and 2-aminobenzothiazoles in good yields. More important, the present reaction process needs only low amounts of copper catalyst (< 1 mol%) and can yield the products on a gram scale.

show abstract

Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds

Cited by 60 publications

References 42 publications

(5Z)-3-(2-Oxopropyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione

(5Z)-3-(2-Oxopropyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione

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

Copper/N,N,N′,N′‐Tetramethylethylenediamine‐Catalyzed Synthesis of N‐Substituted Benzoheterocycles via CS Cross‐ Coupling at Ambient Temperature in Water

Contact Info

Product

Resources

About