Synthesis of 5-alkenylated D4T analogues via the Pd-catalyzed cross-coupling reaction.
The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2',3'-didehydro-2',3'-dideoxy-uridine (12) and 5-[N-[5-(methoxycarbonyl)-pentyl]-acrylamide]-2',3'-didehydro-2',3'- dideoxy-uridine (15) were prepared by the palladium acetate-triphenylphosphine-catalyzed reaction of the 5'-O-acetyl-5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screened for their anti-HIV activity. The biological data demonstrated that none of them were active against HIV-1.
Ciurea
A
A
Centre d'Etudes et de Recherche sur le Médicament de Normandie UFR des Sciences Pharmaceutiques, Caen, France.
Fossey
C
C
Benzaria
S
S
Gavriliu
D
D
Delbederi
Z
Z
Lelong
B
B
Ladurée
D
D
Aubertin
A M
AM
Kirn
A
A
D002384:Catalysis / Q000187:drug effects; D002460:Cell Line; D002855:Chromatography, Thin Layer; D015497:HIV-1 / Q000187:drug effects / Q000201:enzymology / Q000502:physiology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry* / Q000494:pharmacology; D012194:RNA-Directed DNA Polymerase / Q000378:metabolism; D017550:Spectroscopy, Fourier Transform Infrared; D018119:Stavudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015215:Zidovudine / Q000494:pharmacology
D015215:Zidovudine; D010165:Palladium; D018119:Stavudine; D012194:RNA-Directed DNA Polymerase; D014529:Uridine