1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil | 1321580-93-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil
• 英文别名: [(2R,3R,5R)-3-benzoyloxy-4,4-difluoro-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 1321580-93-1
• 化学式: C₂₃H₁₇F₂IN₂O₇
• 分子量: 598.298
• InChiKey: WYCNMXGVVXSJRM-CBGDNZLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以92%的产率得到1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 2′-deoxy-2′,2′-difluoro-5-halouridine phosphoramidate ProTides

  摘要：

  We report the synthesis of a series of novel 2'-deoxy-2',2'-difluoro-5-halouridines and their corresponding phosphoramidate ProTides. All compounds were evaluated for antiviral activity and for cellular toxicity. Interestingly, 2'-deoxy-2',2'-difluoro-5-iodo- and -5-bromo-uridines showed selective activity against feline herpes virus replication in cell culture due to a specific recognition (activation) by the virus-encoded thymidine kinase. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.037
• 作为产物：
  描述：

  2-脱氧-2,2-二氟戊呋喃糖-1-酮 3,5-二安息香酸盐 在 三氟甲磺酸三甲基硅酯 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 1,1-二氯乙烷 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil 、 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranos-1-yl)-5-iodouracil
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 2′-deoxy-2′,2′-difluoro-5-halouridine phosphoramidate ProTides

  摘要：

  We report the synthesis of a series of novel 2'-deoxy-2',2'-difluoro-5-halouridines and their corresponding phosphoramidate ProTides. All compounds were evaluated for antiviral activity and for cellular toxicity. Interestingly, 2'-deoxy-2',2'-difluoro-5-iodo- and -5-bromo-uridines showed selective activity against feline herpes virus replication in cell culture due to a specific recognition (activation) by the virus-encoded thymidine kinase. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.037