Synthesis of novel acyclic nucleoside analogues with anti-retroviral activity.
A series of novel acyclic thymine nucleoside analogues were prepared by the Mitsunobu reaction from appropriately protected chiral triols. The enantiomeric triols were obtained from substituted gamma-lactone acids, prepared by asymmetric oxidation of 3-substituted-1,2-cyclopentanediones. The cytotoxic activity of new analogues was evaluated on MCF-7 human breast cancer and HeLa cells, and antiviral activities on human immunodeficiency virus type 1 and hepatitis C virus models. The synthesized compounds revealed specific anti-retroviral activity and no cytotoxic side effects.
Paju
A
A
Department of Chemistry, Tallinn University of Technology, Tallinn, Estonia.
Päri
M
M
Selyutina
A
A
Zusinaite
E
E
Merits
A
A
Pehk
T
T
Siirde
K
K
Müürisepp
A-M
AM
Kailas
T
T
Lopp
M
M
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004583:Electrons; D006678:HIV / Q000187:drug effects; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D007783:Lactones / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012995:Solubility; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D007783:Lactones; D009705:Nucleosides