79233-64-0Relevant academic research and scientific papers
Ureido-based peptidomimetic inhibitors of herpes simplex virus ribonucleotide reductase: An investigation of inhibitor bioactive conformation
Moss, Neil,Beaulieu, Pierre,Duceppe, Jean-Simon,Ferland, Jean-Marie,Gauthier, Jean,Ghiro, Elise,Goulet, Sylvie,Guse, Ingrid,Llinàs-Brunet, Montse,Plante, Raymond,Plamondon, Louis,Wernic, Dominik,Déziel, Robert
, p. 2178 - 2187 (2007/10/03)
We have been investigating peptidomimetic inhibitors of herpes simplex virus (HSV) ribonucleotide reductase (RR). These inhibitors bind to the HSV RR large subunit and consequently prevent subunit association and subsequent enzymatic activity. This report
Iminium Salts from α-Amino Acid Decarbonylation. Application to the Synthesis of Octahydroindoloquinolizines
Johansen, Jon E.,Christie, Bradley D.,Rapoport, Henry
, p. 4914 - 4920 (2007/10/02)
Iminium salts, formed regiospecifically by the decarbonylation of tertiary α-amino acids, have been applied to the synthesis of substituted tetrahydro-β-carbolines.In this manner the octahydroindoloquinolizines 5-8 were prepared.Several useful methods for the synthesis of the requisite tertiary pipecolic acids 1-4 were developed.These include alkylation of secondary α-amino esters with tryptophyl bromide and alkylation of tryptophan methyl ester with α,ω-dibromo esters.Following deprotection, the resulting tertiary α-amino acids were heated in phenylphosphonic dichloride to give the cyclized products in good yield.The presence of other substituents α or β to the basic nitrogen induces stereoselectivity in the ring closure.When this substituent is an α-carboxylic acid, it can be replaced by hydrogen through decarbonaylation followed by reduction of the resulting iminium salt.
