• Title/Summary/Keyword: Antiviral

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Synthesis and Antiviral Activity of Novel Exomethylene Cyclopropyl Pyrimidine Nucleosides

  • Kook, Min-Chul;Kim, Gu;Kwak, Eun-Yee;Hong, Joon-Hee;Lee, Chong-Kyo;Choi, Bo-Gil
    • Archives of Pharmacal Research
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    • v.25 no.6
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    • pp.790-794
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    • 2002
  • A series of novel exomethylene cyclopropyl nucleosides have been synthesized starting from Feist's acid. Classical nucleophilic substitution conditions ($K_2CO_3$, 18-crown-6) of the tosylate 2 as well as Mitsunobu reaction (DEAD, $PPh_3$) of alcohol 1 with pyrimidine bases afforded a series of novel cyclopropyl nucleosides. Compound 4b displayed moderate anti-HBV activity without any cytotoxicity up to $100{\;}{\mu}M$.

Synthesis and Biological Evaluation of 9-[2-Fluoro-4-hydroxy-3-hydroxymethyl-2-butenyl]adenine and its Related Compounds as Open-chain Analogues of Neplanocin A

  • Choi, Myung-Hee;Kim, Hee-Doo
    • Archives of Pharmacal Research
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    • v.20 no.5
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    • pp.501-506
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    • 1997
  • Novel 9-[2-fluoro-4-hydroxy-3-hydroxymethyl-2-butenyl]adenine and its related compounds were designed and synthesized as open-chain analogues of neplanocin A. Alkylation of adenine or pyrimidine bases with the mesylate 4 was chosen as a simple approach to the synthesis of 2-fluoro-2-butenylated nucleosides. Mesylate 4 was prepared from dihydroxyacetone dimer via four steps in 58% overall yield. The synthesized compounds were evaluated their antiviral activity against HSV, HIV and Polio viruses.

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Synthesis and Some Properties of 4'-Phenyl-5'-Norcarbocyclic Adenosine Phosphonic Acid Analogues

  • Liu, Lian Jin;Kim, Eun-Ae;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1662-1668
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    • 2011
  • Steric and electronic parameters of 4'-substituents play significant roles in steering the conformation of nucleoside analogues. In order to investigate the relationship of 4'-substituent with antiviral enhancement, novel 4'-phenyl-5'-norcarbocyclic adenosine phosphonic acid analogues were racemically synthesized via de novo acyclic stereoselective route from propionaldehyde 5. The phenyl substituted cyclopentenols 15a and 15b as key intermediates were successfully constructed via reiterative carbonyl addition of Grignard reagents and ring-closing metathesis of corresponding divinyl 14. The synthesized nucleoside phosphonic acids analogues 19, 20, 21, and 23 were subjected to antiviral screening against HIV-1.

Host Innate Immunity against Hepatitis E Virus and Viral Evasion Mechanisms

  • Kang, Sangmin;Myoung, Jinjong
    • Journal of Microbiology and Biotechnology
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    • v.27 no.10
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    • pp.1727-1735
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    • 2017
  • Hepatitis E virus (HEV) infections cause epidemic or sporadic acute hepatitis, which are mostly self-limiting. However, viral infection in immunocompromised patients and pregnant women may result in serious consequences, such as chronic hepatitis and liver damage, mortality of the latter of which reaches up to 20-30%. Type I interferon (IFN)-induced antiviral immunity is known to be the first-line defense against virus infection. Upon HEV infection in the cell, the virus genome is recognized by pathogen recognition receptors, leading to rapid activation of intracellular signaling cascades. Expression of type I IFN triggers induction of a barrage of IFN-stimulated genes, helping the cells cope with viral infection. Interestingly, some of the HEV-encoded genes seem to be involved in disrupting signaling cascades for antiviral immune responses, and thus crippling cytokine/chemokine production. Antagonistic mechanisms of type I IFN responses by HEV have only recently begun to emerge, and in this review, we summarize known HEV evasion strategies and compare them with those of other hepatitis viruses.

Synthesis of Novel 2'(β)-Methyl-5'-deoxyapiose Nucleoside Phosphonic Acid Analogues as Antiviral Agents

  • Hong, Joon Hee
    • Journal of Integrative Natural Science
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    • v.8 no.1
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    • pp.48-55
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    • 2015
  • Novel 2'(${\beta}$)-methyl-5'-deoxyapiose purine phosphonic acid analogues were designed and synthesized from 2-propanone-1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbr${\ddot{u}}$ggen conditions. Condensation of aldehyde 14 with Wittig reagent [(diethoxyphosphinyl)methylidene] triphenylphosphorane gave the desired nucleoside phosphonate analogues 15. Ammonolysis and hydrolysis of phosphonates gave the nucleoside phosphonic acid analogue 17 and 19. The synthesized nucleoside analogues were subjected to antiviral screening against HIV-1. The adenine analogue 19 exhibited weak in vitro activities against HIV-1.