Stereospecific synthesis and biological evaluations of beta-L-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine.
In the search for new chemotherapeutic agents, we have focused our work on the synthesis and the study of several unnatural beta-L-nucleoside analogues. In this paper, we report on the synthesis of beta-L-pentofuranonucleosides (and their 2'-deoxy derivatives) of 5-fluorouracil and their inhibitory effects on the proliferation of several murine and human tumor cells. The corresponding 5-fluorocytosine derivatives were also synthesized and their anti-HIV and anti-HBV activities have been evaluated.
Griffon
J F
JF
Laboratoire de Chimie Organique Biomoléculaire de Synthèse, UMR 5625 CNRS-UM II, Université Montpellier II, case courrier 008, Place Eugène Bataillon, F-34095 Montpellier, France.
Mathé
C
C
Faraj
A
A
Aubertin
A M
AM
De Clercq
E
E
Balzarini
J
J
Sommadossi
J P
JP
Gosselin
G
G
D000818:Animals; D019380:Anti-HIV Agents / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D002455:Cell Division / Q000187:drug effects; D015195:Drug Design; D005437:Flucytosine / Q000031:analogs & derivatives*; D005472:Fluorouracil / Q000031:analogs & derivatives*; D006678:HIV / Q000187:drug effects; D006801:Humans; D051379:Mice; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013601:T-Lymphocytes / Q000166:cytology / Q000187:drug effects / Q000276:immunology; D014407:Tumor Cells, Cultured
D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D009705:Nucleosides; D005437:Flucytosine; D005472:Fluorouracil