37529-27-4Relevant articles and documents
Design and synthesis of boronic acid inhibitors of endothelial lipase
O'Connell, Daniel P.,Leblanc, Daniel F.,Cromley, Debra,Billheimer, Jeffrey,Rader, Daniel J.,Bachovchin, William W.
, p. 1397 - 1401 (2012/03/26)
Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL.
Synthesis of Thiamacrocycles and Conformational Studies on Their Precursors
Abramovitch, Rudolph A.,Ye, Xiaocong,Pennington, William T.,Schimek, George,Bogdal, Dariuz
, p. 343 - 351 (2007/10/03)
1-(4-Nitrophenyl)-7-phenylthioheptane (1) and -9-phenylthiononane (2) have been synthesized and their conformations studied in solution and in the solid state. MMX calculations suggest that the global energy minimum structures are bent in the gas phase, probably owing to edge-to-face intramolecular attractive interaction between the electron rich and the electron poor terminal aryl groups. These conformations were confirmed in solution using 2D NOESY NMR. In the solid state, 1 and 2 exist in the staggered, linear conformation, stacked head-to-tail, with the plane of the nitro group being tilted above the plane of the benzene ring. It appears that the crystal lattice forces overcome the weak edge-to-face intramolecular aromatic interactions that dominate in the gas phase and in solution. The corresponding azides were treated with trifluoromethanesulfonic acid to generate the nitrenium ions, which underwent intramolecular ring-closure to give the corresponding 17- and 19-membered ring thiamacrocycles in modest yields. These results support the suggestion that MMX calculations on appropriate model compounds may be useful in predicting which precursors will lead to macrocycles and which will not.
Rates and Regioselectivities of the Palladium-Catalyzed Ethynylation of Substituted Bromo- and Dibromobenzenes
Singh, Rina,Just, George
, p. 4453 - 4457 (2007/10/02)
The Pd(0)/Cu2Br2-catalyzed ethynylation of 1,2-dibromo-4-nitro- and 1,2-dibromo-3-nitrobenzenes provide rapidly the product in which the bromine para or ortho to the nitro group is displaced, whereas the corresponding dibromoacetamidobenzenes provide the product of meta displacement slowly.Investigation of the rates of a series of para-substituted bromobenzenes indicates that the reaction is zero-order with respect to the heptyne and bromobenzene concentration, with a Hammett ρ value of 2.8.
