7515-46-0Relevant articles and documents
Studies on the mechanism, selectivity, and synthetic utility of lactone reduction using SmI2 and H2O
Parmar, Dixit,Duffy, Lorna A.,Sadasivam, Dhandapani V.,Matsubara, Hiroshi,Bradley, Paul A.,Flowers II, Robert A.,Procter, David J.
supporting information; experimental part, p. 15467 - 15473 (2010/02/16)
Although simple aliphatic esters and lactones have long been thought to lie outside the reducing range of SmI2, activation of the lanthanide reagent by H2O allows some of these substrates to be manipulated in an unprecedented fashion. For example, the SmI2-H2O reducing system shows complete selectivity for the reduction of 6-membered lactones over other classes of lactones and esters. The kinetics of reduction has been studied using stopped-flow spectrophotometry. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron-transfer to the lactone carbonyl. The radical intermediates formed during lactone reduction with SmI2-H2O can be exploited in cyclizations to give cyclic ketone (or ketal) products with high diastereoselectivity. The cyclizations constitute the first examples of ester-alkene radical cyclizations in which the ester carbonyl acts as an acyl radical equivalent.
Synthesis and pharmacological characterization of novel inverse agonists acting on the viral-encoded chemokine receptor US28
Hulshof, Janneke W.,Vischer, Henry F.,Verheij, Mark H.P.,Fratantoni, Silvina A.,Smit, Martine J.,de Esch, Iwan J.P.,Leurs, Rob
, p. 7213 - 7230 (2007/10/03)
G-protein coupled receptors encoded by viruses represent an unexplored class of potential drug targets. In this study, we describe the synthesis and pharmacological characterization of the first class of inverse agonists acting on the HCMV-encoded receptor US28. It is shown that replacement of the 4-hydroxy group of lead compound 1 with a methylamine group results in a significant 6-fold increase in affinity. Interestingly, increasing the rigidity of the spacer by the introduction of a double bond also leads to a significant increase in binding affinity compared to 1. These novel inverse agonists serve as valuable tools to elucidate the role of constitutive signaling in the pathogenesis of viral infection and may have therapeutic potential as leads for new antiviral drugs.
Amination of arenes through electron-deficient reaction cascades of aryl epoxyazides
Lang, Stuart,Kennedy, Alan R.,Murphy, John A.,Payne, Andrew H.
, p. 3655 - 3658 (2007/10/03)
(Matrix presented) Aryl epoxyazides undergo efficient electron-deficient reaction cascades mediated by Lewis acids, leading to regiospecific amination of the aromatic ring.
