2,2,5,5-Tetramethylcyclohexane-1,4-dione

Synthesis and fluorescence studies of nine 1,5-benzodiazepine-2,4-dione derivatives: Dual emission and excimer fluorescence.[Pubmed:27894000]

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Mar 5;174:164-170.

The photophysical properties of nine 1,5-benzodiazepine-2,4-dione (BZD) derivatives were investigated using absorption and fluorescence spectral techniques in dimethyl sulfoxide. The trend of red shifts caused by the substitutions had full compliance with the trend of decreasing the calculated band gap (DeltaELUMO-HOMO) by semi-empirical AM1 and DFT/B3LYP/6-311+G* computational methods. The positive solvatochromism of BZD a demonstrated the pi-pi* nature of the singlet excited state. Dual fluorescence was observed in the emission spectra of BZD f and g, while their spectrum in different concentration showed only one peak short wavelength (SW) in dilute solutions. The main peak in SW around 370nm was attributed to the monomer of BZD (f* or g*) and the broader emission shifted to the visible region around 400nm in middle wavelength (MW) to the intermolecular excimer emission of BZD ([f/f]*or [g/g]*). The observed phenomena, such as solvatochromism, dual fluorescence, some red shifts caused by substitution, and larger Stokes shift indicated the existence of intramolecular charge transfer (ICT) in the BZDs series. The phosphorescence emission of the BZDs demonstrated their intersystem crossing (ISC) process.

Synthesis, biological evaluation and in silico studies of 5-(3-methoxybenzylidene)thiazolidine-2,4-dione analogues as PTP1B inhibitors.[Pubmed:28126289]

Bioorg Chem. 2017 Apr;71:1-9.

PTP1B (protein tyrosine phosphatase 1B) dephosphorylates the insulin receptor substrate and thus acts as a negative regulator of the insulin and leptin signalling pathway. Recently, it has been considered as a new therapeutic target of intervention for the treatment of type2 diabetes. A series of aryl/alkylsulfonyloxy-5-(3-methoxybenzylidene)thiazolidine-2,4-dione derivatives were synthesized, screened in vitro for their PTP1B inhibitory activity and in vivo for anti-hyperglycaemic activity. Docking results further helped in understanding the nature of interactions governing the binding mode of ligands inside the active site of PTP1B. Among the synthesized compounds, 13 and 16 were found to be potent PTP1B inhibitors having IC50 of 7.31 and 8.73muM respectively. Significant lowering of blood glucose level was observed in some of the synthesized compounds in in vivo study.

Programmable self-assembly of water-soluble organo-heterometallic cages [M12M'4L12] using 3-(3,5-dimethyl-1H-pyrazol-4-yl)pentane-2,4-dione (H2L).[Pubmed:28361135]

Chem Commun (Camb). 2017 Apr 11;53(30):4238-4241.

A bifunctional ligand H2L featuring primary (pyrazole) and secondary (acetylacetone) coordination sites was preferentially reacted with dimetallic [M2(NO3)2](NO3)2 linkers at the pyrazolyl end of H2L, giving rise to dimetallic corners. Subsequently, the corners serve as the secondary site with M' to form water-soluble organo-heterometallic [M12M'4L12] cages in a stepwise mode.

Protective Effects of 2-Dodecyl-6-Methoxycyclohexa-2,5 -Diene-1,4-Dione Isolated from Averrhoa Carambola L. (Oxalidaceae) Roots on High-Fat Diet-Induced Obesity and Insulin Resistance in Mice.[Pubmed:27941348]

Cell Physiol Biochem. 2016;40(5):993-1004.

BACKGROUND/AIMS: The roots of Averrhoa carambola L. (Oxalidaceae) have long been used as a traditional Chinese medicine for the treatment of diabetes and diabetes-related diseases. 2-dodecyl-6-methoxycycyclohexa-2,5-1,4-dione (DMDD) has been isolated from A. carambola L. roots, and this study was carried out to investigate the potential beneficial effects of DMDD on obesity and insulin resistance induced by a high-fat diet (HFD) in mice. METHODS: C57BL/6J mice were fed a HFD for 16 weeks and orally administered DMDD (12.5, 25, or 50 mg/kg of body weight per day) and metformin (280 mg/kg of body weight per day) for the last 4 weeks. RESULTS: The body weights and adipose tissue weights as well as the serum levels of blood glucose, total cholesterol, triglycerides, free fatty acids, insulin, interleukin-6, and tumor necrosis factor-alpha were significantly decreased by DMDD, and the expression of Toll-like receptor 4 (TLR4) and myeloid differentiation factor (Myd88) in the epididymal adipose tissue was downregulated by DMDD. In contrast, insulin sensitivity was enhanced. The results of the glucose tolerance tests, insulin tolerance tests, and insulin release tests indicated that there was a marked improvement in insulin secretion, and the areas under the curve corresponding to the three tests were also significantly decreased by DMDD. The activities of superoxide dismutase and glutathione peroxidase were simultaneously enhanced, whereas the content of malondialdehyde was decreased by DMDD in the liver homogenates of the C57BL/6J mice. In addition, hepatic steatosis and adipocyte hypertrophy, as assessed by H&E staining of liver and adipose tissues, were significantly improved by DMDD. CONCLUSION: These data suggest that MDD has potential benefits for the treatment of HFD-induced obesity and insulin resistance, and its effects may be associated with improvements in lipid metabolism and inhibition of the expression of TLR4 in adipose tissues.