3',4-di-O-benzoyl-2'-deoxy-5-fluorouridine | 1071792-51-2

• 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: 3',4-di-O-benzoyl-2'-deoxy-5-fluorouridine
• 英文别名: 3'-4-di-O-benzoyl-5-fluoro-2'-deoxyuridine
• CAS: 1071792-51-2
• 化学式: C₂₃H₁₉FN₂O₇
• 分子量: 454.411
• InChiKey: HTWUCRCQOGCNJH-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  116.95
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3',4-di-O-benzoyl-2'-deoxy-5-fluorouridine 在 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  ETHYNYLATED HETERODINUCLEOSIDE PHOSPHATE ANALOGS, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF

  摘要：

  该发明涉及新颖的乙炔基杂二核苷酸磷酸盐类似物，其生产，含有至少一种该化合物的物质，以及将其用于治疗癌症和传染病。

  公开号：

  US20100151001A1
• 作为产物：
  描述：

  在 对甲苯磺酸 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.33h， 生成 3',4-di-O-benzoyl-2'-deoxy-5-fluorouridine
  参考文献：
  名称：

  ETHYNYLATED HETERODINUCLEOSIDE PHOSPHATE ANALOGS, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF

  摘要：

  该发明涉及新颖的乙炔基杂二核苷酸磷酸盐类似物，其生产，含有至少一种该化合物的物质，以及将其用于治疗癌症和传染病。

  公开号：

  US20100151001A1

文献信息

• Synthesis and in vitro activities of new anticancer duplex drugs linking 2′-deoxy-5-fluorouridine (5-FdU) with 3′-C-ethynylcytidine (ECyd) via a phosphodiester bonding
  作者：Herbert Schott、Sarah Schott、Reto A. Schwendener

  DOI：10.1016/j.bmc.2009.08.033

  日期：2009.10

  Two isomeric cytostatic duplex drugs 2'-deoxy-5-fluorouridylyl-(3'-> 5')-3'-C-ethynylcytidine [5-FdU(3'-> 5')ECyd] and 2'-deoxy-5-fluorouridylyl-(5'-> 5')-3'-C-ethynylcytidine [5-FdU(5'-> 5')ECyd] were designed and synthesized at gram scale according to the hydrogenphosphonate method in an overall yield of about 40%. The in vitro evaluation of the anticancer effects indicated highly varying sensibilities of the panel of 60 tested tumor cell lines against the duplex drugs. 5-FdU(3'-> 5')ECyd had a 50% growth inhibition (IC50 <= 10 (8) M) in 44/58 cell lines. However, only 25/53 of those cell lines showed corresponding IC50 values when the isomeric 5-FdU(5'-> 5')ECyd was tested. Total growth inhibition was achieved using micromolar concentrations of the duplex drugs. The 5-FdU residue of the duplex drug can cause very different effects like additive, synergistic, antagonistic as well as sequence-depending activities, which drastically changed efficiency as well as specificity of the anticancer activities of the duplex drugs, in comparison to those of the monomeric drugs. (C) 2009 Elsevier Ltd. All rights reserved.