92105-39-0Relevant academic research and scientific papers
Aniline-Based Inhibitors of Influenza H1N1 Virus Acting on Hemagglutinin-Mediated Fusion
Leiva, Rosana,Barniol-Xicota, Marta,Codony, Sandra,Ginex, Tiziana,Vanderlinden, Evelien,Montes, Marta,Caffrey, Michael,Luque, F. Javier,Naesens, Lieve,Vázquez, Santiago
, p. 98 - 118 (2018/02/10)
Two series of easily accessible anilines were identified as inhibitors of influenza A virus subtype H1N1, and extensive chemical synthesis and analysis of the structure-activity relationship were performed. The compounds were shown to interfere with low pH-induced membrane fusion mediated by the H1 and H5 (group 1) hemagglutinin (HA) subtypes. A combination of virus resistance, HA interaction, and molecular dynamics simulation studies elucidated the binding site of these aniline-based influenza fusion inhibitors, which significantly overlaps with the pocket occupied by some H3 HA-specific inhibitors, indicating the high relevance of this cavity for drug design.
Topologically Controlled Coulombic Interactions, a New Tool in the Developing of Novel Reactivity. Photochemical and Electrochemical Cleavage of Phenyl Alkyl Ethers
Marquet, Jorge,Cayon, Eduard,Martin, Xavier,Casado, Francisco,Gallardo, Iluminada,et al.
, p. 3814 - 3825 (2007/10/02)
The hypothesis that a specific placement of a positive charge would dramatically alter the behavior of a charged intermediate has been tested.Phenyl ethers substituted by electron-attracting groups do not undergo reductive fragmentation.However, related α-piperidino-ω-(4-substituted-phenoxy)alkanes give alkyl ether photocleavage when the linker between the redox centers is short, or the usual substitution-reduction photochemistry when it is long.Mechanistic experiments suggest that the photofragmentation process operates through space intramolecular electron transfer to the triplet aromatic chromophore and that a coplanar relative orientation of the alkyl ether bond and the phenyl ring is compulsory for the photofragmentation to be observed.Configuration interaction AM1 calculations justify the described facts, indicating that the fragmentation process is only operative when a Coulombic stabilization of a ?* intramolecular electron transfer excited state is produced.Electrochemical studies carried out with the corresponding quaternary salts (intermolecular generation of the phenyl ether radical anion) confirm the conclusions derived from the photochemical experiments.
