5-[3-(4-benzoylphenoxy)prop-1-ynyl]-2'-deoxyuridine | 877643-17-9

• 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: 5-[3-(4-benzoylphenoxy)prop-1-ynyl]-2'-deoxyuridine
• 英文别名: 5-[3-(4-benzoylphenoxy)prop-1-ynyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione；5-[3-(4-benzoylphenoxy)prop-1-ynyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 877643-17-9
• 化学式: C₂₅H₂₂N₂O₇
• 分子量: 462.459
• InChiKey: YOLVKRHGFUVIHM-BHDDXSALSA-N

物化性质

• 熔点：
  98-100 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-羟基-二苯甲酮 在 四(三苯基膦)钯 copper(l) iodide 、 triethylamine trihydrofluoride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 28.0h， 生成 5-[3-(4-benzoylphenoxy)prop-1-ynyl]-2'-deoxyuridine
  参考文献：
  名称：

  5-Alkynyl-2′-deoxyuridines, containing bulky aryl groups: evaluation of structure–anti-HSV-1 activity relationship

  摘要：

  Four 5-alkynyl-2-deoxyuridines containing different bulky substituents and flexible linkers between the triple bond and the aromatic residue have been prepared and tested against HSV-1 in Vero cells. Two nucleosides containing carbonyl groups, 5-(4-benzoylphenoxypropyn-1-yl)-2'-deoxyutidine (19a) and 5-(estron-3-yloxypropyn-1-yl)-2'-deoxyuridine (19c), showed low cytotoxicity and moderate antiviral activity. The flexible linker appears not to be favorable for antiviral properties of 5-alkynyl-2'deoxyuridines: 5-[(perylen-3-yl)methoxypropyn-1-yl]-2'-deoxyuridine (19d) showed considerable cytotoxicity and no antiviral activity in contrast to the active and nontoxic 5-(perylen-3-ylethynyl)-2'-deoxyuridine (9), a nucleoside with a rigid triple-bond-connection of the aromatic system to the nucleobase. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.057

文献信息

• SYNTHESIS AND EVALUATION OF ANTI-HSV ACTIVITY OF NEW 5-ALKYNYL-2′-DEOXYURIDINES
  作者：A. A. Pchelintseva、M. V. Skorobogatyj、A. L. Petrunina、V. L. Andronova、G. A. Galegov、I. V. Astakhova、A. V. Ustinov、A. D. Malakhov、Vladimir A. Korshun

  DOI：10.1081/ncn-200059280

  日期：2005.4.1

  Eight 5-alkynyl-2'deoxyuridines containing different bulky substituents have been prepared and tested against HSV-1 in Vero cells. The compounds show positive antiviral activity. There is no obvious correlation between activity and substituent size. The nature of the linker between uracil and a substituent appears to be more important for antiviral properties: nucleosides containing arylethynyl groups show higher activity.
• 5-Alkynyl-2′-deoxyuridines, containing bulky aryl groups: evaluation of structure–anti-HSV-1 activity relationship
  作者：Mikhail V. Skorobogatyi、Anna A. Pchelintseva、Anna L. Petrunina、Irina A. Stepanova、Valeriya L. Andronova、Georgi A. Galegov、Andrei D. Malakhov、Vladimir A. Korshun

  DOI：10.1016/j.tet.2005.10.057

  日期：2006.2

  Four 5-alkynyl-2-deoxyuridines containing different bulky substituents and flexible linkers between the triple bond and the aromatic residue have been prepared and tested against HSV-1 in Vero cells. Two nucleosides containing carbonyl groups, 5-(4-benzoylphenoxypropyn-1-yl)-2'-deoxyutidine (19a) and 5-(estron-3-yloxypropyn-1-yl)-2'-deoxyuridine (19c), showed low cytotoxicity and moderate antiviral activity. The flexible linker appears not to be favorable for antiviral properties of 5-alkynyl-2'deoxyuridines: 5-[(perylen-3-yl)methoxypropyn-1-yl]-2'-deoxyuridine (19d) showed considerable cytotoxicity and no antiviral activity in contrast to the active and nontoxic 5-(perylen-3-ylethynyl)-2'-deoxyuridine (9), a nucleoside with a rigid triple-bond-connection of the aromatic system to the nucleobase. (c) 2005 Elsevier Ltd. All rights reserved.