475294-53-2Relevant academic research and scientific papers
Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction
Carlet, Federica,Bertarini, Greta,Broggini, Gianluigi,Pradal, Alexandre,Poli, Giovanni
, p. 2162 - 2168 (2021/04/02)
A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.
A concise synthesis of Pawhuskin A
Neighbors, Jeffrey D.,Buller, Matthew J.,Boss, Kelly D.,Wiemer, David F.
scheme or table, p. 1949 - 1952 (2009/09/06)
Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.
Synthesis and 11c-labelling of (E,E)-1-(3′,4′-dihydroxystyryl)-4-(3′-methoxy-4 ′-hydroxystyryl) benzene for PET imaging of amyloid deposits
Wang, Yanming,Mathis, Chester A.,Huang, Guo-Feng,Holt, Daniel P.,Debnath, Manik L.,Klunk, William E.
, p. 647 - 664 (2007/10/03)
Carboxylic acid derivatives of the amyloid-binding dye Congo red do not enter the brain well and are thus unable to serve as in vivo amyloid-imaging agents. A neutral amyloid probe, (E,E)-1-(3′,4′-dihydroxystyryl)-4-(3′-methoxy-4 ′-hydroxystyryl)benzene (3), devoid of any carboxylate groups has been designed and synthesized via a 12-step reaction sequence with a total yield of 30%. The unsymmetric compound 3 has also been labelled with C-11 via [11C]methyl iodide ([11C]CH3I) methylation of a symmetric 4,4′-dimesyl protected precursor followed by deprotection. Preliminary evaluation indicated that compound 3 selectively stained plaques and neurofibrillary tangles in post-mortem AD brain, and exhibited good binding affinity (Ki = 38 ± 8 nM) for Aβ(1-40) fibrils in vitro. In vivo pharmacokinetic studies indicated that [11C]3 exhibited higher brain uptake than its carboxylic acid analogs and good clearance from normal control mouse brain. [11C]3 also exhibited specific in vivo binding to pancreatic amyloid deposits in the NOR-beta transgenic mouse model. These results justify further investigation of 3 and similar derivatives as surrogate markers for in vivo quantitation of amyloid deposits. Copyright
