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Synthesis of novel phosphorylated peptidomimetics which contain ω-haloalkyl and ω-thiocyanoethyl residues

The interaction of (2-aryl-5-(hydroxyalkylamino)-1,3-oxazol-4-yl)phosphonates with hydrogen chloride, hydrogen iodide and hydrogen thiocyanate in anhydrous medium led to formation of new phosphorylated peptidomimetics containing C-terminal ω-haloalkyl and ω-thiocyanoethyl residues. | Synthesis of novel phosphorylated peptidomimetics which contain ω-haloalkyl and ω-thiocyanoethyl residues Current Chemistry Letters 9 2020 131 142 Contents lists available at GrowingScience Current Chemistry Letters homepage www.GrowingScience.com Synthesis of novel phosphorylated peptidomimetics which contain ω-haloalkyl and ω-thiocyanoethyl residues Oleksandr V. Golovchenkoa Esma R. Abdurakhmanovaa Mykhailo Y. Brusnakova Serhii O. Vladimirovb Yulia O. Shyshatskab Olga V. Khilyab Yulian M. Volovenkob and Volodymyr S. Brovaretsa a V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of National Academy of Sciences of Ukraine Ukraine b Taras Shevchenko National University of Kyiv Ukraine CHRONICLE ABSTRACT Article history The interaction of 2-aryl-5- hydroxyalkylamino -1 3-oxazol-4-yl phosphonates with Received July 19 2019 hydrogen chloride hydrogen iodide and hydrogen thiocyanate in anhydrous medium led to Received in revised form formation of new phosphorylated peptidomimetics containing C-terminal ω-haloalkyl and ω- December 19 2019 thiocyanoethyl residues. Accepted December 19 2019 Available online December 19 2019 Keywords 1 3-Oxazoles Phosphonates Phosphorylated peptidomimetics Hydrogen halogenides Hydrogen thiocyanate 2020 Growing Science Ltd. All rights reserved. 1. Introduction It is known that 1 3-oxazole derivatives are reactive compounds and can be converted to other five- and six-membered rings.1-10 In addition 1 3-oxazoles are unstable in an acidic medium and are cleaved by a water molecule to form acyclic products.11 12 In the case of 4-functionalized 5-amino-1 3-oxazoles this leads to formation of compounds of peptide nature. Particular attention is drawn to the derivatives of 5-amino-1 3-oxazol-4-ylphosphonic acids which under conditions of acidic cleavage form peptidomimetics containing the residues of phosphorylated glycine.13-19 High biological activity of phosphorus-containing peptides is known. For example selective inhibitors of