346689-79-0Relevant academic research and scientific papers
Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane
Clarke, Joshua J.,Maekawa, Yuuki,Nambo, Masakazu,Crudden, Cathleen M.
supporting information, p. 6617 - 6621 (2021/09/02)
Mesoionic carbene-stabilized borenium ions efficiently reduce substituted pyridines to piperidines in the presence of a hydrosilane and a hydrogen atmosphere. Control experiments and deuterium labeling studies demonstrate reversible hydrosilylation of the pyridine, enabling full reduction of the N-heterocycle under milder conditions. The silane is a critical reaction component to prevent adduct formation between the piperidine product and the borenium catalyst.
Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp3 C-Si Bonds
Gandhamsetty, Narasimhulu,Park, Sehoon,Chang, Sukbok
supporting information, p. 15176 - 15184 (2015/12/18)
Tris(pentafluorophenyl)borane-catalyzed silylative reduction of pyridines has been developed giving rise to the formation of sp3 C-Si bonds selectively beta to the nitrogen atom of azacyclic products. Depending on the position and nature of pyridine substituents, structurally diverse azacycles are obtained with high selectivity under the borane catalysis. Mechanistic studies elucidated the sequence of hydrosilylation in this multiple reduction cascade: 1,2- or 1,4-hydrosilylation as an initial step depending on the substituent position, followed by selective hydrosilylation of enamine double bonds eventually affording β-silylated azacyclic compounds.
Synthesis and structure-activity relationships for 1-(4-(piperidin-1- ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3
Heinrich, Daniel M.,Flanagan, Jack U.,Jamieson, Stephen M.F.,Silva, Shevan,Rigoreau, Laurent J.M.,Trivier, Elisabeth,Raynham, Tony,Turnbull, Andrew P.,Denny, William A.
supporting information, p. 738 - 744 (2013/05/09)
High expression of the aldo-keto reductase enzyme AKR1C3 in the human prostate and breast has implicated it in the development and progression of leukemias and of prostate and breast cancers. Inhibitors are thus of interest as potential drugs. Most inhibitors of AKR1C3 are carboxylic acids, whose transport into cells is likely dominated by carrier-mediated processes. We describe here a series of (piperidinosulfonamidophenyl)pyrrolidin-2-ones as potent (100 nM) and isoform-selective non-carboxylate inhibitors of AKR1C3. Structure-activity relationships identified the sulfonamide was critical, and a crystal structure showed the 2-pyrrolidinone does not interact directly with residues in the oxyanion hole. Variations in the position, co-planarity or electronic nature of the pyrrolidinone ring severely diminished activity, as did altering the size or polarity of the piperidino ring. There was a broad correlation between the enzyme potencies of the compounds and their effectiveness at inhibiting AKR1C3 activity in cells.
Potent non-nucleoside inhibitors of the measles virus RNA-dependent RNA polymerase complex
Sun, Aiming,Yoon, Jeong-Joong,Yin, Yan,Prussia, Andrew,Yang, Yutao,Min, Jaeki,Plemper, Richard K.,Snyder, James P.
scheme or table, p. 3731 - 3741 (2009/04/10)
Measles virus (MV) is one of the most infectious pathogens known. In spite of the existence of a vaccine, approximately 350000 deaths/year result from MV or associated complications. Antimeasles compounds could conceivably diminish these statistics and pr
