Novel acyclic amide-conjugated nucleosides and their analogues.
An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.
Boncel
Slawomir
S
Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Gliwice, Poland. slawomir.boncel@polsl.pl
Walczak
Krzysztof
K
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D009025:Morpholines / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C467606:4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; D000577:Amides; D009025:Morpholines; D009705:Nucleosides; D014498:Uracil; C011166:5-aminouracil