[(2S)-4-(2,4-dioxopyrimidin-1-yl)-1,3-dioxolan-2-yl]methyl benzoate | 232282-95-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: [(2S)-4-(2,4-dioxopyrimidin-1-yl)-1,3-dioxolan-2-yl]methyl benzoate
• CAS: 232282-95-0
• 化学式: C₁₅H₁₄N₂O₆
• 分子量: 318.286
• InChiKey: PZDBZBTZPWBLGV-ABLWVSNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S)-4-(2,4-dioxopyrimidin-1-yl)-1,3-dioxolan-2-yl]methyl benzoate 在 劳森试剂 、 羟胺 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  N ⁴-Hydroxycytosine Dioxolane Nucleosides and Their Activity Against Hepatitis B Virus

  摘要：

  Novel racemic, D- and L-beta-dioxolane N-4-hydroxycytosine nucleosides have been synthesized and evaluated for their activity against hepatitis B virus. None of the synthesized nucleosides demonstrated selective anti-HBV activity.

  DOI：

  10.1081/ncn-200067414
• 作为产物：
  描述：

  (2S)-4-acetoxy-2-(benzoyloxymethyl)-1,3-dioxolane 、 尿嘧啶 在 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S)-4-(2,4-dioxopyrimidin-1-yl)-1,3-dioxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  N ⁴-Hydroxycytosine Dioxolane Nucleosides and Their Activity Against Hepatitis B Virus

  摘要：

  Novel racemic, D- and L-beta-dioxolane N-4-hydroxycytosine nucleosides have been synthesized and evaluated for their activity against hepatitis B virus. None of the synthesized nucleosides demonstrated selective anti-HBV activity.

  DOI：

  10.1081/ncn-200067414

文献信息

• Structure−Activity Relationships of <scp>l</scp>-Dioxolane Uracil Nucleosides as Anti-Epstein Barr Virus Agents
  作者：Ju-Sheng Lin、Toshihiko Kira、Elizabeth Gullen、Yongseok Choi、Fucheng Qu、Chung K. Chu、Yung-Chi Cheng

  DOI：10.1021/jm9806749

  日期：1999.6.1

  A series of 1,3-dioxolanyluracil analogues was prepared from the dioxolane intermediates 2, and their anti-Epstein Barr virus (anti-EBV) activities were detemined. The potency of L-dioxolane uracil nucleosides against EBV replication is dependent bn the substituents at the 5-position in the following decreasing order: I > Br > Cl > CH3 > CF3 > F. The most active and selective analogue was the iodo derivative (L-I-OddU) with an EC50 value of 0.03 mu M and an EC90 value of 0.16 mu M. There was no cytotoxicity or depletion of mitochondrial DNA in cells after exposure to L-I-OddU at 50 mu M. The action against EBV replication. in H1 cells is time-dependent, and EBV DNA in cells treated with L-I-OddU could rebound to pretreatment levels once the drug was removed. In view of the potent antiviral activity plus favorable toxicity profiles, L-I-OddU may be potentially useful for the treatment of EBV-related infectious diseases as well as for delaying the onset or decreasing the incidence of EBV-associated cancers.
• <i>N</i> ⁴-Hydroxycytosine Dioxolane Nucleosides and Their Activity Against Hepatitis B Virus
  作者：Jinfa Du、Laurent Hollecker、Junxing Shi、Byoung-Kwon Chun、Kyoichi A. Watanabe、Raymond F. Schinazi、Tammy Y. Nachman、Stefania Lostia、Lieven J. Stuyver、Michael J. Otto

  DOI：10.1081/ncn-200067414

  日期：2005.7.1

  Novel racemic, D- and L-beta-dioxolane N-4-hydroxycytosine nucleosides have been synthesized and evaluated for their activity against hepatitis B virus. None of the synthesized nucleosides demonstrated selective anti-HBV activity.