23530-42-9Relevant articles and documents
Direct Synthesis of Allyl Amines with 2-Nitrosulfonamide Derivatives via the Tsuji-Trost Reaction
Bon, Corentin,Arimondo, Paola B.,Halby, Ludovic
, p. 1166 - 1169 (2021/08/17)
The Tsuji-Trost Reaction is a palladium-catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen-based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2-nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2-nitrosulfonyl groups are well-known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2-nitrosulfonamide derivatives are ideal substrates for the Tsuji-Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives.
Tweaking Subtype Selectivity and Agonist Efficacy at (S)-2-Amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propionic acid (AMPA) Receptors in a Small Series of BnTetAMPA Analogues
Wang, Shuang-Yan,Larsen, Younes,Navarrete, Cristina Vara,Jensen, Anders A.,Nielsen, Birgitte,Al-Musaed, Ali,Frydenvang, Karla,Kastrup, Jette Sandholm,Pickering, Darryl S.,Clausen, Rasmus Pr?torius
supporting information, p. 2244 - 2254 (2016/03/25)
A series of analogues of the (S)-2-Amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)propionic acid (AMPA) receptor agonist BnTetAMPA (5b) were synthesized and characterized pharmacologically in radioligand binding assays at native and cloned AMPA receptors and functionally by two-electrode voltage clamp electrophysiology at the four homomeric AMPA receptors expressed in Xenopus laevis oocytes. The analogues 6 and 7 exhibit very different pharmacological profiles with binding affinity preference for the subtypes GluA1 and GluA3, respectively. X-ray crystal structures of three ligands (6, 7, and 8) in complex with the agonist binding domain (ABD) of GluA2 show that they induce full domain closure despite their low agonist efficacies. Trp767 in GluA2 ABD could be an important determinant for partial agonism of this compound series at AMPA receptors, since agonist efficacy also correlated with the location of the Trp767 side chain.
Nickel-catalyzed regio- and enantioselective annulation reactions of 1,2,3,4-benzothiatriazine-1,1(2H)-dioxides with allenes
Miura, Tomoya,Yamauchi, Motoshi,Kosaka, Akira,Murakami, Masahiro
supporting information; experimental part, p. 4955 - 4957 (2010/10/02)
(Figure Presented) Extrusion of N2:1,2,3,4-Benzothiatriazine1,1 (2H)-dioxides reacted with alienes in the presence of a nickel (0)/(R)-quinap complex to produce a variety of substituted 3,4-dihydro-1,2-benzothiazine1,1 (2H)-dioxides in a regio- and enantioselective fashion. An intermediate nickelacycle was generated through denitrogenative activation of the triazo moiety which allowed the intermolecular incorporation of an aliene group. quinap = 1-(2diphenylphosphino-1-naphthyl)isoquinoline.