Synthesis and in vitro cytotoxic and antiviral activities of 1-(2,5,6-trideoxy-6-halogenohept-5-enofuranurononitrile)thymine and derivatives.
All 1-(2,5,6-trideoxy-6-halogenohept-5-enofuranurononitrile)thymine and their 3'-O-TBDMS derivatives have been prepared and their configuration established. Some of these compounds are endowed with a cytotoxic or cytostatic activity in cell culture. The single most important factor affecting the cytotoxicity of these compounds is the presence on the molecule of a soft (electrofugal) halogen atom.
Tronchet
Jean M J
JM
Department of Organic Pharmaceutical Chemistry, University of Geneva, Sciences II, Switzerland.
Chalard
Frederic
F
Rivara-Minten
Elisabeth
E
Seman
Michel
M
De Clercq
Erik
E
Balzarini
Jan
J
Dilda
Pierre
P
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D017646:Organosilicon Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D013941:Thymine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000998:Antiviral Agents; D017646:Organosilicon Compounds; C009660:t-butyldimethylsilyl compounds; D013941:Thymine