- Synthesis and biological evaluation of novel isothiazoloquinoline quinone analogues
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Natural quinones and their analogues have attracted growing attention because of their novel anticancer activities. A series of novel isothiazoloquinoline quinone analogues were synthesized and evaluated for antitumor activities against four different kind of cancer cells. Among them, isothiazoloquinolinoquinones inhibited cancer cells proliferation effectively with IC50 values in the nanomolar range, and isothiazoloquinolinoquinone 13a induced the cell apoptosis. Further exploration of possible mechanism of action indicates that 13a not only activates ROS production through NQO1-directed redox cycling but also inhibits the phosphorylation of STAT3. These findings indicate that 13a has potential use for the development of new skeleton drug candidate as an efficient substrate of NQO1 and STAT3 inhibitor.
- Chen, Ling,Gao, Jin-Lei,Hao, Ying,Kong, Fan-Rong,Liu, Hong-Dou,Liu, Li-Jun,Liu, Su-You,Luo, Zhi-Yong,Ma, Da-You,Wang, Liu-Liu,Xie, Yuan-Zhu,Zou, Zi-Zheng
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supporting information
(2020/06/22)
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- ISOTHIAZOLE-PYRIDINE DERIVATIVES AS MODULATORS OF HIF (HYPOXIA INDUCIBLE FACTOR) ACTIVITY
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The present invention relates to novel compounds according to Formula I or II, methods, and compositions capable of decreasing HIF hydroxylase enzyme activity, thereby increasing the stability and/or activity of hypoxia inducible factor (HIF). Formula (I) or (II).
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Page/Page column 66
(2009/09/04)
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- Structure and stability of small nitrile sulfides and their attempted generation from 1,2,5-thiadiazoles
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The gas-phase generation and spectroscopic identification of nitrile sulfides by thermolysis of 1,2,5-thiadiazole precursors was attempted, but in all cases the thiadiazoles were found to produce sulfur and the corresponding nitrile. This prompted an investigation by ab initio and density functional calculations for the equilibrium geometries, stabilities, and decomposition mechanisms of several nitrile sulfides (XCNS, where X = H, F, Cl, CN, CH3). Equilibrium geometries obtained from calculations at the B3LYP, MPn(n = 2-4), QCISD, QCISD(T), CCSD, and CCSD(T) levels with moderate to large basis sets indicate that the molecules have linear heavy atom geometries. The exception is the fluoro derivative, which is bent with a calculated barrier to linearity of 889 cm-1 (B3LYP/cc-pVTZ). The nitrile sulfides are predicted by the B3LYP method to be stable in the dilute gas phase, whereas in the condensed phase they are suggested to be very unstable due to bimolecular decomposition. The mechanism of this loss process is complicated by various sulfur transfer and cyclization reactions between decomposition intermediates, with the predicted stable products being sulfur, nitriles, and thiadiazoles. The first step of the bimolecular decomposition is either a cycloaddition to thiofuroxan or a sulfur transfer with simultaneous S2 loss to nitriles.
- Pasinszki, Tibor,Karpati, Tamas,Westwood, Nicholas P. C.
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p. 6258 - 6265
(2007/10/03)
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- Dithiazoles and Related Compounds. Part 3. Preparation of 5H-1,4,2-Dithiazoles via 1,3-Dipolar Cycloadditions between Nitrile Sulphides and Thiocarbonyl Compounds, and some Conversions into 3,5-Diaryl-1,4,2-dithiazolium Salts
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Thermolysis of 1,3,4-oxathiazol-2-ones 3 in the presence of thiocarbonyl compounds gives modest to good yields of the little-known 5H-1,4,2-dithiazoles 1, the reaction being successful with diaryl, aryl alkyl and dialkyl ketones, and thiono esters, but failing with dithio esters and tertiary thioamides.The influence of substituents is discussed.Solvolysis of 5-ethoxy-5H-1,4,2-dithiazoles, derived from thiono esters, with perchloric acid in acetic anhydride gives high yields of 3,5-diaryl-1,4,2-dithiazolium salts 9.
- Wai, Kwok-Fai,Sammes, Michael P.
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p. 183 - 187
(2007/10/02)
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