1374765-38-4Relevant academic research and scientific papers
The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement
Szczes?niak, Piotr,Pieczykolan, Micha?,Stecko, Sebastian
, p. 1057 - 1074 (2016)
An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.
Flow synthesis and biological studies of an analgesic adamantane derivative that inhibits P2X7-evoked glutamate release
Battilocchio, Claudio,Guetzoyan, Lucie,Cervetto, Chiara,Di Cesare Mannelli, Lorenzo,Frattaroli, Daniela,Baxendale, Ian R.,Maura, Guido,Rossi, Antonietta,Sautebin, Lidia,Biava, Mariangela,Ghelardini, Carla,Marcoli, Manuela,Ley, Steven V.
supporting information, p. 704 - 709 (2013/09/02)
We report the biological evaluation of a class of adamantane derivatives, which were achieved via modified telescoped machine-assisted flow procedure. Among the series of compounds tested in this work, 5 demonstrated outstanding analgesic properties. This compound showed that its action was not mediated through direct interaction with opioid and/or cannabinoid receptors. Moreover, it did not display any significant anti-inflammatory properties. Experiments carried out on rat cerebrocortical purified synaptosomes indicated that 5 inhibits the P2X7-evoked glutamate release, which may contribute to its antinociceptive properties. Nevertheless, further experiments are ongoing to characterize the pharmacological properties and mechanism of action of this molecule.
A flow-based synthesis of 2-aminoadamantane-2-carboxylic acid
Battilocchio, Claudio,Baxendale, Ian R.,Biava, Mariangela,Kitching, Matthew O.,Ley, Steven V.
supporting information; experimental part, p. 798 - 810 (2012/08/27)
The development of a new, high-yielding, scalable and safe process for the preparation of 2-aminoadamantane-2-carboxylic acid (1) is described. This geminal, functionalized achiral amino acid has been reported to possess interesting biological activity as
