156832-31-4Relevant academic research and scientific papers
Altering the Stereochemistry of Allylation Reactions of Cyclic α-Sulfinyl Radicals with Diarylureas
Curran, Dennis P.,Kuo, Lung Huang
, p. 3259 - 3261 (1994)
Radical allylations of 2-(phenylseleno)tetrahydrothiophene oxide and 2-benzyl-5-(phenylseleno)-3-isothiazolidone 1-oxide with allyltributylstannane in the presence of N,N-bis urea have been investigated.This urea was shown to be about as selective as promoting formation of trans-2-allyltetrahydrothiophene oxide and trans-5-allyl-2-benzyl-3-isothiazolidone 1-oxide as hydrogen bonding solvents and Lewis acids.
Activation of Electron-Deficient Quinones through Hydrogen-Bond-Donor-Coupled Electron Transfer
Turek, Amanda K.,Hardee, David J.,Ullman, Andrew M.,Nocera, Daniel G.,Jacobsen, Eric N.
supporting information, p. 539 - 544 (2016/02/27)
Quinones are important organic oxidants in a variety of synthetic and biological contexts, and they are susceptible to activation towards electron transfer through hydrogen bonding. Whereas this effect of hydrogen bond donors (HBDs) has been observed for Lewis basic, weakly oxidizing quinones, comparable activation is not readily achieved when more reactive and synthetically useful electron-deficient quinones are used. We have successfully employed HBD-coupled electron transfer as a strategy to activate electron-deficient quinones. A systematic investigation of HBDs has led to the discovery that certain dicationic HBDs have an exceptionally large effect on the rate and thermodynamics of electron transfer. We further demonstrate that these HBDs can be used as catalysts in a quinone-mediated model synthetic transformation.
2-Chloro-4-(trifluoromethyl)pyrimidine-5-N-(3',5'- bis(trifluoromethyl)phenyl)carboxamide: A potent inhibitor of NF-κB- and AP- 1-mediated gene expression identified using solution-phase combinatorial chemistry
Sullivan, Robert W.,Bigam, Colin G.,Erdman, Paul E.,Palanki, Moorthy S. S.,Anderson, David W.,Goldman, Mark E.,Ransone, Lynn J.,Suto, Mark J.
, p. 413 - 419 (2007/10/03)
Described is the identification of a novel series of compounds that blocks the activation of two key transcription factors, AP-1 and NF-κB. These transcription factors regulate the expression of several critical proinflammatory proteins and cytokines and represent attractive targets for drug discovery. Through the use of high throughput screening and solution- phase parallel synthesis, inhibitors of both NF-κB and AP-1 were identified. In subsequent testing, these compounds were also shown to block both IL-2 and IL-8 levels in the same cells. One of the most potent compounds in this series, 28, was active in several animal models of inflammation and immunosuppression, thus validating the importance of AP-1 and NF-κB as potential therapeutic targets. The synthesis and preliminary structure- activity relationships of these compounds is addressed.
