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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 IC 50 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 IC 50 values, T21 was the most effective compound with IC 50 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. This article is open to POST-PUBLICATION REVIEW . Registered readers (see “For Readers”) may comment by clicking on ABSTRACT on the issue’s contents page.

The antioxidant properties of 11 new synthesized chromonyl-2,4-thiazolidinediones and chromonyl-2,4-imidazolidinediones (CBs) were investigated. The antioxidant activities and mechanisms of the CBs interaction with reactive oxygen species (ROS) were clarified using various in vitro antioxidant assay methods including superoxide anion radical (O2(•-)), hydroxyl radical (HO(•)), 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH(•)) scavenging activity and the iron (II)-ferrozine complex formation. The potassium superoxide/18-crown-6 ether dissolved in dimethylsulfoxide (DMSO) was applied as a source of superoxide anion radical. Hydroxyl radicals were produced in the Fenton-like reaction Fe(II)+H2O2. Chemiluminescence, spectrophotometry, and electron paramagnetic resonance (EPR) spectroscopy using 5,5-dimethyl-1-pyrroline-1-oxide (DMPO) as spin trap were applied as the measurement techniques. The CBs examined that exhibited good free radical scavenging activity also showed strong total antioxidant power capacity. Possible mechanisms of antioxidation are proposed to explain the differences in the experimental results between the chromone derivatives with imidazolidine-2,4-dione ring and those with thiazolidine-2,4-dione ring. In conclusion, some of the new CBs are promising to be applied as inhibitors of free radicals.

A series of chromonyl-2,4-thiazolidinediones/imidazolidinediones/2-thioxo-imidazolidine-4-ones (IIIa-i, IVa-i) was prepared by Knoevenagel reaction of 2,4-thiazolidinedione/2,4-imidazolidinedione/2-thioxo-imidazolidine-4- one (IIa-c) with 2/3-formyl chromone (Ia-b) and then alkylation with methyl/ethyl iodide. The prepared compounds were tested for their insulinotropic activities in INS-1 cells. Compounds iVb and iVc (at lower concentration, 1 mu g/mL) were able to increase insulin release in the presence of 5.6 mmol/L glucose." should be written as "Compounds IVb and IVc (at lower concentration, 1 mu g/mL) and also IIId and IIIg (at higher concentration) were able to increase insulin release in the presence of 5.6 mmol/L glucose. Compounds iVb and iVc (at lower concentration, 1 mu g/mL) were able to increase insulin release in the presence of 5.6 mmol/L glucose.

Kazak, Canan/0000-0003-2475-8775; Bozdag Dundar, Oya/0000-0002-2240-8854; UNLUSOY, Meltem CEYLAN/0000-0002-7070-8181 WOS: 000326745800010 PubMed: 23057864 Numerous compounds have been prepared in order to improve the pharmacological profile of insulinotropic activities. In the present paper, we report the synthesis and the in vitro insulin releasing activity of the 6-methyl-chromonyl-2,4-thiazolidinediones (IIIa-c, IVa-c, Va-c). Compounds IIIb, IIIc, IVa-c, Va and Vc (at lower concentration; 0.001 mg/mL) were able to increase insulin release in the presence of 5.6 mmol/L glucose. In this series, the most potent compound is IVa having methyl group at N3 position of TZD ring. Research Organization of Ankara University, TurkeyAnkara University [09B3336003] This work was supported by Research Organization of Ankara University, Turkey (No: 09B3336003).

The scavenging effects of eighteen thiazolyl thiazolidine-2,4-dione compounds (TTCs) on superoxide radical , hydroxyl radical HO•, and 1,1-diphenyl-2-picrylhydrazyl (DPPH•) radical were evaluated by the chemiluminescence technique, electron spin resonance spectrometry (ESR) and visible spectrophotometry, respectively. The examined compounds were shown to have 27–59% scavenging ability, 19–69% HO• scavenging activity and 2–32% DPPH• scavenging ability. This property of the tested compound seems to be important in the prevention of various diseases of free radicals etiology. Copyright © 2009 John Wiley & Sons, Ltd.

A series of thiazolyl-2,4-thiazolidine-diones (Ia-f, IIa-f and IIIa-f) was prepared by Knoevenagel reaction of substituted benzyl-2,4-thiazolidinediones (4a-f) with chlorothiazolecarbaldehydes (2, 3a-b). The prepared compounds were tested for their insulinotropic activities in INS-1 cells.. A significant insulinotropic effect was seen with compounds If and IIa.

A new series of furochromone-2,4-thiazolidinedione derivatives (VIIa-h) was prepared by Knoevenagel reaction of substituted-2,4-thiazolidinediones (VIa-h) with Khellin-2-carboxaldehyde (IV). The prepared compounds were tested for their insulinotropic activities in INS-1 cells. Compounds VIId and VIIf (at lower concentration; 1 microgram/ml) were able to increase insulin release in the presence of 5.6 mmol/l glucose. Both these compounds (VIId and VIIf) and VIIg increased glucose uptake in NIH-3T3 cells. Thus these 3 compounds should be tested for antidiabetic effects in vivo.

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.