3-Cyanopyridine(cas: 100-54-9) has been shown to have a number of pharmacological effects: it inhibits the production of prostaglandin E2 and nitric oxide in congestive heart failure patients; it prevents the formation of diazonium salt from benzene and nitrogen dioxide; it inhibits the growth of tumor cell lines; and it protects mice from radiation injury by scavenging reactive oxygen species. Category: pyridine-derivatives
Zhang, Xuan;Nottingham, Kyle G.;Patel, Chirag;Alegre-Requena, Juan V.;Levy, Jeffrey N.;Paton, Robert S.;McNally, Andrew published 《Phosphorus-mediated sp2-sp3 couplings for C-H fluoroalkylation of azines》. The research results were published in《Nature (London, United Kingdom)》 in 2021.Category: pyridine-derivatives The article conveys some information:
Fluoroalkyl groups profoundly affect the phys. properties of pharmaceuticals and influence almost all metrics associated with their pharmacokinetic and pharmacodynamic profile. Drug candidates increasingly contain trifluoromethyl (CF3) and difluoromethyl (CF2H) groups, and the same trend in agrochem. development shows that the effect of fluoroalkylation translates across human, insect and plant life. New fluoroalkylation reactions have undoubtedly stimulated this shift; however, methods that directly convert C-H bonds into C-CF2X groups (where X is F or H) in complex drug-like mols. are rare. Pyridines are the most common aromatic heterocycles in pharmaceuticals, but only one approach – via fluoroalkyl radicals – is viable for achieving pyridyl C-H fluoroalkylation in the elaborate structures encountered during drug development. Here we develop a set of bench-stable fluoroalkylphosphines that directly convert the C-H bonds in pyridine building blocks, drug-like fragments and pharmaceuticals into fluoroalkyl derivatives No preinstalled functional groups or directing groups are required. The reaction tolerates a variety of sterically and electronically distinct pyridines, and is exclusively selective for the 4-position in most cases. The reaction proceeds through initial formation of phosphonium salts followed by sp2-sp3 coupling of phosphorus ligands – an underdeveloped manifold for forming C-C bonds. Thus, e.g., treatment of 2-phenylpyridine with (fluoroalkyl)phosphine I, Tf2O and DBU afforded intermediate phosphonium salt (not isolated) which, upon treatment with TfOH, MeOH and water afforded II (89%). And 3-Cyanopyridine (cas: 100-54-9) was used in the research process.
3-Cyanopyridine(cas: 100-54-9) has been shown to have a number of pharmacological effects: it inhibits the production of prostaglandin E2 and nitric oxide in congestive heart failure patients; it prevents the formation of diazonium salt from benzene and nitrogen dioxide; it inhibits the growth of tumor cell lines; and it protects mice from radiation injury by scavenging reactive oxygen species. Category: pyridine-derivatives
Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem