• 제목/요약/키워드: SATE prodrug

검색결과 3건 처리시간 0.016초

Synthesis of SATE Prodrug of 6'-Fluoro-6'-methyl-5'-noradenosine Nucleoside Phosphonic Acid as a New Class of Anti-HIV Agent

  • Li, Hua;Yoo, Jin-Cheol;Baik, Young-Chan;Lee, Won-Jae;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • 제31권9호
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    • pp.2514-2518
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    • 2010
  • A very simple synthetic route of a novel SATE prodrug type of 6'-fluoro-6'-methyl-5'-noradeonosine carbocyclic nucleoside phosphonic acid is described. The key fluorinated alcohol intermediate 7 was prepared from the epoxide intermediate 6a via selective ring-opening of epoxide. Coupling of 7 with $N^6$-bis-Boc-adenine under a Mitsunobu reaction followed by phosphonation and deprotection afforded the carbocyclic phosphonic acid. The chemical stability of the bis(SATE) derivative 13 was measured at neutral (pH 7.2) and slightly acidic (Milli-Q water, pH 5.5) pH. The antiviral activity test of the SATE prodrug 13 and its parent nucleoside phosphonic acid 11 were evaluated against HIV-1.

Antiviral Activity Enhancement through the SATE Prodrug of a 2'-Modified 5'-Norcarbocyclic Adenine Analogue

  • Li, Hua;Kim, Si-Wouk;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • 제31권8호
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    • pp.2180-2184
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    • 2010
  • We synthesized and tested the anti-HIV activity of the SATE prodrug of a 2'-methyl 5'-norcarbocyclic adenine analogue. The introduction of a methyl group in the 2'-position was performed by the addition of a carbonyl using isopropenyl magnesium bromide. The adenine base was efficiently coupled using the Mitsunobu reaction. The chemical stability study of the bis(SATE) derivative 18 was measured at neutral (pH 7.2) and slightly acid (milli-Q water, pH 5.5) pH, and compounds 16 and 18 were evaluated as potential anti-HIV-1 agents.

Synthesis and Anti-HCV Activity of 3',5'-cyclic SATE Phosphonodiester Nucleoside as a Novel Prodrug

  • Liu, Lian Jin;Seo, Rac-Seok;Yoo, Seung-Won;Choi, Jin;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • 제31권4호
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    • pp.915-920
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    • 2010
  • A novel 2',4'-dimethyl carbocyclic adenosine 5'-phosphonic acid analogue (20) was prepared using acyclic stereoselective route from commercially available 4-hydroxybutan-2-one (4). To improve cellular permeability and enhance the anti-HCV activity of this phosphonic acid, a 3',5'-cyclic SATE phosphonodiester nucleoside prodrug (22) was prepared. The synthesized phosphonic nucleoside analogues, (20) and (22), were assayed for their ability to inhibit HCV RNA replication in a subgenomic replicon Huh7 cell line.