• Title/Summary/Keyword: 1'-Branched nucleoside

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Synthesis and Antiviral Activity of Novel 4',5'-Branched Pyrimidine Nucleosides (4',5'-측쇄를 가진 새로운 피리미딘 뉴크레오사이드의 합성 및 항바이러스 약효검색)

  • Kim Aihong;Kooh Dae-Ho;Ko Ok Hyun;Hong Joon Hee
    • YAKHAK HOEJI
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    • v.49 no.1
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    • pp.20-24
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    • 2005
  • The synthesis of 4',5'-doubly branched carbocyclic nucleosides was accomplished in this study. The selective methylation in the 5'-position was made by Felkin-Anh controlled Grignard addition. The construction of the required 4'-quaternary carbon was carried out by using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural pyrimidine bases (cytosine, uracil, thymine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited weak antiviral activity against the HCMV.

Stereoselective Synthesis and Antiviral Activity of Novel 4′(α)-Hydroxymethyl and 6′(α)-Methyl Dually Branched Carbocyclic Nucleosides

  • Kim, Jin-Woo;Choi, Bo-Gil;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.25 no.12
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    • pp.1812-1816
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    • 2004
  • The stereoselective synthesis 4′,6′-dually branched carbocyclic nucleosides was accomplished in this study. The introduction of a methyl group in the 6′$({\alpha})$-position was accomplished by Felkin-Anh controlled alkylation. The construction of the required 4′$({\alpha})$-quaternary carbon was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited good antiviral activity against the HCMV.

Synthesis and Antiviral Activity of Novel 2′-Methyl and 4′-Phenyl Branched Carbocyclic Nucleosides (2′-메칠 및 4′-페닐 측쇄를 가진 새로운 카보사이클릭 뉴크레오사이드의 합성 및 항바이러스 약효검색)

  • 양선화;홍준희
    • YAKHAK HOEJI
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    • v.48 no.1
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    • pp.88-92
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    • 2004
  • In this study; a series of 2',4'-doubly branched carbocyclic nucleosides (8,9,10) were synthesized from simple acyclic ketone derivative as starting material. The installation of the 4'-quaternary carbon needed was carried out using a 〔3,3〕-sigmatropic rearrangement. In addition, the introduction of a methyl group in the 2'-position was accomplished by Grig-nard reaction. Bis-vinyl was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine, uracil) were efficiently coupled with the use of a Pd(0) catalyst. Although all the synthesized compounds were assayed against several viruses, only cytosine analogue 9 showed weak antiviral viral activity (EC$_{50}$=45.4 $\mu$M) against CoxB3 virus.s.

Synthesis and Antiviral Activity of Novel C-Methyl Branched Cyclopropyl Nucleosides

  • Kwak, Eun-Yee;Hong, Joon-Hee;Park, Young-Jak;Choi, Bo-Gil
    • Archives of Pharmacal Research
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    • v.26 no.9
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    • pp.679-685
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    • 2003
  • A series of novel cyclopropyl nucleosides was synthesized using the highly stereoselective Simmons-Smith reaction starting from 1,2:5,6-di-Ο-isopropylidene-D-mannitol. The structural assignments of these nucleosides were determined by NMR studies and X-ray crystallography. All the synthesized nucleosides were assayed against several viruses.

Efficient Synthesis of Novel 4'-Trifluoromethyl-5'-norcarbocyclic Purine Phosphonic Acid Analogs by Using the Ruppert-Prakash Reaction

  • Kim, Seyeon;Kim, Eunae;Yoo, Jin Cheol;Hong, Joon Hee
    • Bulletin of the Korean Chemical Society
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    • v.35 no.9
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    • pp.2743-2748
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    • 2014
  • Novel 4'-trifluoromethyl-5'-norcarbocyclic purine phosphonic acid analogs were efficiently synthesized from commercially available 1,3-dihydroxy cyclopentane (5). Trifluoromethylation was successfully performed by using the Ruppert-Prakash reaction. The purine nucleosidic bases were efficiently coupled by using the Mitsunobu reaction. The synthesized adenosine phosphonic acids analogs 13 and 16 were screened for antiviral activity against human immunodeficiency virus-1 (HIV-1). Adenine derivative 13 exhibited significant anti-HIV-1 activity.