Prodrugs of Ara-CMP and Ara-AMP with a S-acyl-2-thioethyl (SATE) biolabile phosphate protecting group: synthesis and biological evaluation.
The bis(S-pivaloyl-2-thioethyl) phosphotriesters of Ara-C and Ara-A were synthesized as potential bioreversible mononucleotide prodrugs. Some N- and O-acylated derivatives were also prepared with the aim to modify the lipophilicity of the title pronucleotides. Compounds were tested for their antitumor/antiviral activity against a variety of tumor cells and viruses.
Bazzanini
R
R
Consiglio Nazionale delle Ricerche, I.Co.C.E.A., Bologna, Italy. r_bazzanini@area.bo.cnr.it
Manfredini
S
S
Durini
E
E
Gröschel
B
B
Cinatl
J
J
Balzarini
J
J
De Clercq
E
E
Imbach
J L
JL
Périgaud
C
C
Gosselin
G
G
D000249:Adenosine Monophosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D002460:Cell Line; D003568:Cytidine Monophosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D008826:Microbial Sensitivity Tests; D011355:Prodrugs / Q000138:chemical synthesis* / Q000494:pharmacology*
D011355:Prodrugs; D000249:Adenosine Monophosphate; D003568:Cytidine Monophosphate