Open-chain carbocyclic analogs of adenosine with dihalovinyl unit as potential inhibitors of S-adenosyl-L-homocysteine hydrolase.
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.
Lewandowska
Elzbieta
E
Department of Chemistry, Florida International University, Miami, Florida 33199, USA.
Lalama
Jennifer
J
Yuan
Chong-Sheng
CS
Wnuk
Stanislaw F
SF
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry; D043383:Adenosylhomocysteinase / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D008956:Models, Chemical; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry
D004791:Enzyme Inhibitors; D014753:Vinyl Compounds; D043383:Adenosylhomocysteinase; D000241:Adenosine