3-(2'-deoxy-β-D-rybofuranosyl)-6-(3-hydroxy-4-iodophenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 3-(2'-deoxy-β-D-rybofuranosyl)-6-(3-hydroxy-4-iodophenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
• 英文别名: 6-(3-hydroxy-4-iodophenyl)-3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)furo[2,3-d]pyrimidin-2(3H)-one；3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(3-hydroxy-4-iodophenyl)furo[2,3-d]pyrimidin-2-one
• 化学式: C₁₇H₁₅IN₂O₆
• 分子量: 470.22
• InChiKey: NGNSMZWUMDNDPL-NWANDNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  碘苷 在 sodium hydroxide 、 四(三苯基膦)钯 过氧乙酸 、 copper(l) iodide 、 磷酸 、 TEA 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-(2'-deoxy-β-D-rybofuranosyl)-6-(3-hydroxy-4-iodophenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of an 123I-labeled bicyclic nucleoside analogue (BCNA) as potential SPECT tracer for VZV-tk reporter gene imaging

  摘要：

  An iodine-123 labeled bicyclic nucleoside analogue ([I-123]-4) has been synthesized and evaluated as a potential single photon emission tomography (SPECT) reporter probe for the non-invasive imaging of expression of the varicella zoster virus thymidine kinase (VZV-tk) reporter gene. In vitro enzymatic assays revealed that the non-radioactive mono-iodo derivative 4 has good affinity for VZV-TK (IC50: 4.2 mu M). Biodistribution of [I-123]-4 was examined in normal mice. Evaluation of [I-123]-4 in HEK-293T cells showed 1.74-fold higher accumulation in VZV-TK-expressing cells compared to control cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.081

文献信息

• Synthesis and biological evaluation of an 123I-labeled bicyclic nucleoside analogue (BCNA) as potential SPECT tracer for VZV-tk reporter gene imaging
  作者：Satish K. Chitneni、Christophe M. Deroose、Humphrey Fonge、Rik Gijsbers、Natalia Dyubankova、Jan Balzarini、Zeger Debyser、Luc Mortelmans、Alfons M. Verbruggen、Guy M. Bormans

  DOI：10.1016/j.bmcl.2007.03.081

  日期：2007.6

  An iodine-123 labeled bicyclic nucleoside analogue ([I-123]-4) has been synthesized and evaluated as a potential single photon emission tomography (SPECT) reporter probe for the non-invasive imaging of expression of the varicella zoster virus thymidine kinase (VZV-tk) reporter gene. In vitro enzymatic assays revealed that the non-radioactive mono-iodo derivative 4 has good affinity for VZV-TK (IC50: 4.2 mu M). Biodistribution of [I-123]-4 was examined in normal mice. Evaluation of [I-123]-4 in HEK-293T cells showed 1.74-fold higher accumulation in VZV-TK-expressing cells compared to control cells. (c) 2007 Elsevier Ltd. All rights reserved.