Synthesis and biological evaluation of diastereoisomerically pure N,O-nucleosides.
Several N,O-nucleosides have been synthesized in good yields by direct 1,3-dipolar cyclization methodology, in the absence of solvent. A remarkable cis stereoselectivity (de 98%) was observed by tuning the substituents on the nitrone moiety. A good number of these N,O-nucleosides have been evaluated for cytotoxic activity against selected cellular lines. Some of the tested compounds have proven to be potential antiproliferative drugs.
Bortolini
Olga
O
Dipartimento di Chimica, Università della Calabria, Via Bucci 12 C, 87036 Rende (CS), Italy. o.bortolini@unical.it
De Nino
Antonio
A
Eliseo
Tommaso
T
Gavioli
Riccardo
R
Maiuolo
Loredana
L
Russo
Beatrice
B
Sforza
Fabio
F
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D001402:B-Lymphocytes / Q000187:drug effects; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D003500:Cyclization; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D019169:Jurkat Cells / Q000187:drug effects; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D009705:Nucleosides