111697-04-2Relevant 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 (2016/02/19)
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.
The synthesis of neurotensin antagonist SR 48692 for prostate cancer research
Baxendale,Cheung,Kitching,Ley,Shearman
, p. 4378 - 4387 (2013/07/27)
An improved synthesis of the molecule SR 48692 is presented and its use as a neurotensin antagonist biological probe for use in cancer research is described. The preparation includes an number of enhanced chemical conversions and strategies to overcome some of the limiting synthetic transformations in the original chemical route.
A flow-based synthesis of 2-aminoadamantane-2-carboxylic acid
Battilocchio, Claudio,Baxendale, Ian R.,Biava, Mariangela,Kitching, Matthew O.,Ley, Steven V.
body text, 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
Assisted hydrolysis of the nitrile group of 2-aminoadamantane-2-carbonitrile
Paventi, Martino,Chubb, Francis L.,Edward, John T.
, p. 2114 - 2117 (2007/10/02)
Attempts to hydrolyse the nitrile group of 2-aminoadamantane-2-carbonitrile by mineral acid or alkali have been unsuccessful.However, treatment of the aminonitrile with benzaldehyde in alkaline solution gives the benzal derivative of the α-aminoamide, redily hydrolysed to the α-aminoamide.Alternatively, benzoylation of the amino group followed by acid hydrolysis gives successively the α-benzamido acid and the α-amino acid.Possible mechanisms for these facilitated hydrolyses are advanced.
