64379-96-0Relevant articles and documents
Palladium-Catalyzed Regioselective Hydroaminocarbonylation of Alkynes to α,β-Unsaturated Primary Amides with Ammonium Chloride
Ji, Xiaolei,Gao, Bao,Zhou, Xibing,Liu, Zongjian,Huang, Hanmin
, p. 10134 - 10141 (2018/07/09)
α,β-Unsaturated primary amides have found numerous applications in drug development, organic materials, and polymer sciences. However, the catalytic synthesis of α,β-unsaturated primary amides via carbonylation of alkynes has long been an elusive endeavor. Here, we report a novel palladium-catalyzed hydroaminocarbonylation of alkynes with NH4Cl as the amine source, enabling the highly chemo- and regioselective synthesis of α,β-unsaturated primary amides. A variety of alkynes, including aromatic alkynes, aliphatic alkynes, terminal alkynes, internal alkynes, as well as diynes with various functional groups, react well. The method turns the parasitic noncoordination ability of ammonium salts into a strategic advantage, enabling the gram-scale reaction to be performed in the presence of 0.05 mol % of catalyst with excellent selectivity.
A σ1 receptor pharmacophore derived from a series of N-substituted 4-azahexacyclo[5.4.1.02,6.03,10.0 5,9.08,11]dodecan-3-ols (AHDs)
Banister, Samuel D.,Manoli, Miral,Doddareddy, Munikumar Reddy,Hibbs, David E.,Kassiou, Michael
supporting information, p. 6053 - 6058 (2012/10/30)
A library of N-substituted 4-azahexacyclo[5.4.1.02,6.0 3,10.05,9.08,11]dodecan-3-ols (AHDs) was synthesized and subjected to competition binding assays at σ1 and σ2 receptors, as well as off-target screening of representative members at 44 other common central nervous system (CNS) receptors, transporters, and ion channels. Excluding 3 low affinity analogs, 31 ligands demonstrated nanomolar Ki values for either σ receptor subtype. Several selective σ1 and σ2 ligands were discovered, with selectivities of up to 29.6 times for σ1 and 52.4 times for σ2, as well as several high affinity, subtype non-selective ligands. The diversity of structures and σ1 affinities of the ligands allowed the generation of a σ1 receptor pharmacophore that will enable the rational design of increasingly selective and potent σ1 ligands for probing σ1 receptor function.