Open-chain carbocyclic analogs of adenosine with dihalovinyl unit as potential inhibitors of S-adenosyl-L-homocysteine hydrolase

Nucleosides Nucleotides Nucleic Acids. 2003 Sep;22(9):1747-55. doi: 10.1081/NCN-120023270.

Abstract

Vinylogously extended deoxyeritadenine derivatives were synthesized as acyclic/ carbocyclic analogues of the 6'-halo(homovinyl)adenosines, which are known to be potent inhibitors of S-adenosyl-L-homocysteine hydrolase. Swern oxidation of 9-[3-(t-butyldimethylsilyloxy)-4-hydroxybutyl]adenine (4) followed by Wittig olefination and desilylation gave access to ethyl 6-(adenin-9-yl)-4-hydroxy-2(E)-hexenoate (7) and 5-(adenin-9-yl)-1,1-dibromo-1-penten-3-ol (9). No inhibition of AdoHcy Hydrolase was observed with 7 and 9.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemistry
  • Adenosylhomocysteinase / antagonists & inhibitors*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Humans
  • Models, Chemical
  • Molecular Structure
  • Vinyl Compounds / chemistry

Substances

  • Enzyme Inhibitors
  • Vinyl Compounds
  • Adenosylhomocysteinase
  • Adenosine