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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 8
BKCSDE 32(8)
August 20, 2011 

Racemic Synthesis of Novel 6'-Methylene-5'-norcarbocyclic Purine Phosphonic Acid Analogues via Mitsunobu Reaction
Eunae Kim, Lian Jin Liu, Joon Hee Hong *
anti-HIV agents, 6'-Methylene-5'-norcarbocyclic nucleoside, Mitsunobu reaction
Novel 5'-norcarbocyclic adenine and guanine phosphonic acid analogues with 6'-electronegative moiety such as unsaturated C-C bond were designed and synthesized from commercially available 2-methylene-propane- 1,3-diol (4). Regioselective Mitsunobu reaction successfully proceeded from an allylic functional group (±)- 12b at low reaction temperature in polar cosolvent (DMF/1,4-dioxane) to give purine phosphonate analogues (±)-13 and (±)-20. The purine nucleoside phosphonate and phosphonic acid analogues were subjected to antiviral screening against HIV-1. Guanine analogue (±)-23 shows significant anti-HIV activity in PBM cell lines (EC50 = 8.1 μM).
2689 - 2694
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