A new class of acyclic nucleoside phosphonates: synthesis and biological activity of 9-[[(phosphonomethyl)aziridin-1-yl]methyl]guanine (PMAMG) and analogues.
A new class of acyclic nucleoside phosphonates PMAMG, PMAMA, PMAMC, and PMAMT (compounds 1, 2, 3 and 4) have been synthesized and tested in vitro against a wide variety of viruses, fungi and bacteria. PMAMG (1) was synthesized by the alkylation reaction of acetylguanine with the phosphonate side-chain, diisopropyl [[2-(bromomethyl)aziridin-1-yl]]methylphosphonate (9), followed by deesterification reaction in the presence of TMSBr. In similar way, PMAMA, PMAMC, and PMAMT were prepared.
Abu Sheikha
Ghassan
G
Department of Pharmaceutical Chemistry and Pharmacognosy, Applied Sciences University, 11931 Amman, Jordan. abusheikha@yahoo.com
La Colla
Paolo
P
Loi
Anna Giulia
AG
D000478:Alkylation; D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001388:Aziridines / Q000138:chemical synthesis* / Q000494:pharmacology*; D002460:Cell Line; D004951:Esterification; D006147:Guanine / Q000031:analogs & derivatives; D006801:Humans; D008826:Microbial Sensitivity Tests; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000494:pharmacology*; D012760:Shigella / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013289:Streptococcaceae / Q000145:classification / Q000187:drug effects; D013329:Structure-Activity Relationship; D014780:Viruses / Q000187:drug effects; D015003:Yeasts / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000998:Antiviral Agents; D001388:Aziridines; D009705:Nucleosides; D063065:Organophosphonates; D006147:Guanine