Design, synthesis, conformational analysis and biological activities of purine-based 1,2-di-substituted carbocyclic nucleosides.
New 1,2-di-substituted carbocyclic nucleosides with 6-chloropurine, adenine and hypoxanthine bases were synthesized by construction of purine on the primary amino group of (+/-)-trans-2-aminocyclopentylmethanol. AM1 calculations showed close correspondence between the positions of the heteroatoms in the adenine derivative and dideoxyadenosine. The most active of the new compounds in antiviral assays and antitumoral assays against L1210/0, MOLT4/C8 and CEM/0 cells was the 6-chloropurine derivative.
Teran
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C
Departamento de Química Física y Química Orgánica, Universidad de Vigo, Spain.
Santana
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L
Teijeira
M
M
Uriarte
E
E
De Clercq
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E
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000494:pharmacology; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured; D014780:Viruses / Q000187:drug effects
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D003517:Cyclopentanes; D011684:Purine Nucleosides