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-Purpose:A new series of thiazolyl-2,4-thiazolidinedione / rhodanine compounds T1-T23 was synthesized and tested for their anticancer activities. Hepatocellular carcinoma cell lines were chosen due to their strong drug resistance to test the new compounds. Methods: All compounds were synthesized via Knoevenagel Condensation reaction and thiazolidinedione ester compounds (T3,T9,T15,T20) were hydrolyzed for obtaining the acidic compounds (T6,T12,T17,T23). All compounds were firstly screened for their anticancer activity against two hepatocellular carcinoma (HCC) cell lines, Huh7 and Plc/Prf/5 (Plc) cell lines by sulforhodamine B assay. Further IC50 values were calculated for three candidates (T4, T15, T21) in five different HCC (Huh7, Plc, Snu449, HepG2, Hep3B) and one breast cancer (Mcf7) cell line. Results: Compounds T4, T15, T21 had very strong anticancer effects even though their 10 µM concentration in Huh7 cell line. According to IC50 values, T21 was the most effective compound with IC50 values in a range from 2 to 16 µM in 6 cancer cell lines. In terms of cytotoxicity T21 mostly affected Huh7 and interestingly it was less effective against Plc. Conclusions: Considering these results it can be suggested that compounds T4, T15 and T21 may lead to the development of more potent anticancer drugs in the future.

In diabetes, increased flux through the polyol pathway has been implicated in the development of diabetic complications such as cataract, retinopathy, neuropathy, and nephropathy. Aldose reductase (AR) appears to be the key factor in the reduction of glucose to sorbitol. Aldose reductase inhibitors have been found to prevent sorbitol accumulation in tissues. A series of thiazolyl-2,4-thiazolidinediones was prepared by Knoevenagel reaction of substituted benzyl-2,4-thiazolidinediones with chlorothiazolecarbaldehydes and were evaluated for their ability to inhibit rat kidney AR by an in vitro spectrophotometric assay. Results showed that compounds containing piperidine at the C-2 position of thiazole ring showed better inhibitory activity than thiazole compounds having 4-chlorobenzylsulfanyl at the same position.

In this study, a series of 2,4-dichlorothiazolyl thiazolidine-2,4-dione (Iaf) and 4-chloro-2-benzylsulfanylthiazolyl-thiazolidine-2,4-dione derivatives (IIa-f) were tested for their antioxidant properties by determining their effects on superoxide anion formation, and the 2,2-diphenyl-1-picrylhydrazyl (DPPH) stable free radical. Compound Ic showed the best superoxide anion scavenging activity at the 10 -3 M and 10 -4 M concentrations. The compounds (Ia-f and IIa-f) had the strong DPPH radical scavenger capacity at the 10 -3 M concentration. Compound Ib, Id, and Ie showed similar activity to butylated hydroxytoluene (BHT) at 10 -3 M and 10 -4 M concentrations.

Recent reviews evidence that the naturally occurring compounds containing the chromone skeleton exhibit antiradical activities, providing protection against oxidative stress. The antioxidant activities of 13 new synthesized chromonyl-2,4-thiazolidinediones, chromonyl-2,4-imidazolidinediones and chromonyl-2-thioxoimidzolidine-4-ones were evaluated using in vitro antioxidant assays, including superoxide anion radical (O2(-•)), hydroxyl radical (HO(•)), 2,2-diphenyl-1-picryl-hydrazyl free radical (DPPH(•)) scavenging capacity and total antioxidant capacity ferric ion reducing activity. Superoxide anion radical was produced using potassium superoxide/18-crown-6-ether dissolved in dimethylsulfoxide, and the Fenton-like reaction (Fe(II) + H2O2) was a generator of hydroxyl radicals. Chemiluminescence, spectrophotometry, electron paramagnetic resonance (EPR) and 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) as the spin trap were the measurement techniques. The results showed that the majority of the chromone derivatives tested showed a strong scavenging effect towards free radicals, similar to the chemiluminescence reaction with superoxide anion radical with a high activity, inhibition of the DMPO-OOH radical EPR signal (24-58%), the DMPO-OH radical EPR signal (4-75%) and DPPH radical EPR signal (6-100%) at 1 mmol/L. Several of the examined compounds exhibited the high reduction potentials. The results obtained show that the new synthesized chromone derivatives may directly scavenger reactive oxygen species and thus may play a protective role against oxidative damage.

In this study, a series of phenylefhylsul-fanyl-1,3-thiazolo-thiazolidine-2,4-dione derivatives (VII a ?f, VIII a?f) and 5-methyl-[1,2,4] triazolyl-sulfanyl-1,3-fhia-zolo-thiazolidine-2,4-dione derivatives (IXa?f, Xa?f) were synthesized and evaluated for their antibacterial and antifungal activities against S. aureus (ATCC 25923), methicillin resistant S. aureus (MRSA ATCC 43300), B. subtilis (ATCC 6633), E. coli (ATCC 23556) and C. albicans (ATCC10145). All the compounds were found active against used bacteria.

A series of flavonyl-2,4-thiazolidinedione, imidazolidinedione and rhodanine derivatives were tested for their antioxidant activity as scavengers of oxygen free radicals. Free radical scavenging activities, including superoxide anion radical O2•, hydroxyl radical (HO(•)) and 2,2'-diphenyl-1-picrylhydrazyl free radical have been evaluated using chemiluminescence, electron paramagnetic resonance and spin trapping with 5,5-dimethyl-1-pyrroline-1-oxide as a spin trap. Potassium superoxide in dimethylsulfoxide and 18-crown-6 ether were used for the production of O2•. Hydroxyl radical was generated using the Fenton reaction. Ten of the eleven examined compounds exhibited decrease in chemiluminescence, but there were large differences in the decrease, ranging from 16% to 89%; also, two of these compounds increased light emission by about 200%. On the contrary, all compounds tested exhibited 30-68% scavenging HO(•) and 25-96% scavenging the DPPH(•) radical respectively. Possible mechanisms are proposed to explain the results.

A series of chromonyl-2,4-thiazolidinediones (VIa-f) and chromonyl-2,4-imidazolidinediones (VIIa-f) was prepared by Knoevenagel reaction of substituted benzyl-2,4-thiazolidinediones (IVa-f) and substituted benzyl-2,4-imidazolidinediones (Va-f) with chromone-3-carboxaldehyde (I). The prepared compounds were tested for their insulinotropic activities in INS-1 cells. Compounds VIa, VIb, VId and VIIe (at lower concentration; 1 microg/ml) were able to increase insulin release in the presence of 5.6 mmol/l glucose; their effects were lower than that of glibenclamide (CAS 10238-21-8). The activity of the most potent compound (VId) was still 9% less than that of glibenclamide.