255833-23-9Relevant academic research and scientific papers
Synthesis and structure-activity relationships of novel, potent, orally active hypoxia-inducible factor-1 inhibitors
Nagao, Satoshi,Yamane, Yoshinobu,Funasaka, Setsuo,Tanaka, Keigo,Miyazaki, Kazuki,Kotake, Yoshihiko,Kamata, Jun-Ichi,Watanabe-Miyano, Saori,Toyama, Osamu,Ozawa, Yoichi,Mizui, Yoshiharu,Okamoto, Kiyoshi,Ito, Daisuke
, p. 5513 - 5529 (2014/12/10)
Hypoxia-inducible factor-1 (HIF-1) is the chief transcription factor regulating hypoxia-driven gene expression. HIF-1 overexpression is associated with poor prognosis in several cancers and therefore represents an attractive target for novel antitumor agents. We explored small molecule inhibitors of the HIF-1 pathway. Using high-throughput-screening, we identified benzanilide compound 1 (IC50= 560 nM) as a seed. Subsequent extensive derivatization led to the discovery of compounds 43a and 51d, with anti-HIF-1 activities in vitro (IC50= 21 and 0.47 nM, respectively), and in vivo. Additionally, 43a (12.5-100 mg/kg) also displayed in vivo anti-tumor efficacy, without influencing body weight.
Synthesis and photoluminescent properties of conjugated aryl-vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives
Bosiak, Mariusz J.,Rakowiecki, Marcin,Or?owska, Katarzyna J.,K?dziera, Dariusz,Adams, J?rg
, p. 803 - 811 (2013/09/12)
The synthesis of highly fluorescent conjugated benzodifuran aryl-vinyl systems, containing four double bonds and at least four phenyl rings, is described. The ethyl groups of diethyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7- dicarboxylate, obtained by the Michael type condensation of p-benzoquinone and ethyl acetoacetate, were replaced by octyl groups via the transesterification reaction to improve the desired product solubility in common organic solvents. The dioctyl ester was brominated and used for the Wittig reaction with stilbene aldehydes, obtained by the Heck reaction of 4-bromobenzaldehyde and an appropriate styrene. The products, obtained in 48-92% yield, exhibit the UV-Vis fluorescence with high quantum yields, 58-69%.
Identification of 5-arylidene-4-thiazolidinone derivatives endowed with dual activity as aldose reductase inhibitors and antioxidant agents for the treatment of diabetic complications
Ottanà, Rosaria,MacCari, Rosanna,Giglio, Marco,Del Corso, Antonella,Cappiello, Mario,Mura, Umberto,Cosconati, Sandro,Marinelli, Luciana,Novellino, Ettore,Sartini, Stefania,La Motta, Concettina,Da Settimo, Federico
experimental part, p. 2797 - 2806 (2011/07/08)
In continuing the search for more effective 5-arylidene-4-thiazolidinones as aldose reductase inhibitors, a new set of suitably substituted compounds (4, 5 and 8) was explored. Acetic acids 5, particularly 5a and 5h, proved to be interesting inhibitors of the enzyme as well as excellent antioxidant agents that are potentially able to counteract the oxidative stress associated with both diabetic complications as well as other pathologies. Molecular docking experiments supported SAR studies.
Electrocatalytic oxidative cleavage of electron-deficient substituted stilbenes in acetonitrile-water employing a new high oxidation potential electrocatalyst. An electrochemical equivalent of ozonolysis
Wu, Xin,Davis, Anthony P.,Fry, Albert J.
, p. 5632 - 5636 (2008/09/18)
A series of symmetrical and unsymmetrical stilbenes bearing two or more strong electron-withdrawing groups were oxidatively cleaved to the corresponding aldehydes in high yield by electrocatalytic anodic oxidation in aqueous acetonitrile employing a new high oxidation potential triphenylamine electrocatalyst. The oxidations apparently involve the corresponding 1,2-diols, which are also converted to aldehydes in high yield under the same conditions.
