Synthesis of C-5'-nor-dideoxycarbanucleosides structurally related to neplanocin C.
Purine carbanucleosides built on a 6-oxabicyclo[3.1.0]hexane template were synthesized from readily available 2-cyclopentenone employing a Mitsunobu reaction to incorporate the base onto the carbocyclic ring. Both adenosine and guanosine analogues exhibited moderate antiviral activity.
Comin
M J
MJ
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
Pujol
C A
CA
Damonte
E B
EB
Rodriguez
J B
JB
D000241:Adenosine / Q000031:analogs & derivatives / Q000737:chemistry; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002522:Chlorocebus aethiops; D002850:Chromatography, Gel; D003517:Cyclopentanes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects; D014709:Vero Cells
D000998:Antiviral Agents; D003517:Cyclopentanes; D009705:Nucleosides; D011687:Purines; C016329:cyclopentylamine; C031098:neplanocin C; D000241:Adenosine