Synthesis and biological activities of cyclic ADP-carbocyclic-ribose and its analogs.
An efficient synthesis of cyclic ADP-carbocyclic-ribose (2), as a stable mimic for cyclic ADP-ribose, was achieved. Treatment of N1-carbocyclic-ribosyladenosine bisphosphate derivative 10 with AgNO3 in the presence of molecular sieves 3A in pyridine gave the desired cyclic product in 93% yield, which was deprotected to give the target cyclic ADP-carbocyclic-ribose (2).
Fukuoka
M
M
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Shuto
S
S
Minakawa
N
N
Ueno
Y
Y
Matsuda
A
A
D000246:Adenosine Diphosphate Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology / Q000502:physiology; D036563:Cyclic ADP-Ribose / Q000031:analogs & derivatives; D018716:Molecular Mimicry
C439996:cyclic ADP-carbocyclic-ribose; D036563:Cyclic ADP-Ribose; D000246:Adenosine Diphosphate Ribose