Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[5-(5-bromo-thiophen-2-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester | 170453-11-9

• 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: Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[5-(5-bromo-thiophen-2-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester
• CAS: 170453-11-9
• 化学式: C₁₇H₁₇BrN₂O₇S
• 分子量: 473.301
• InChiKey: FJQDARUEVZHWLQ-YWPYICTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  116.69
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[5-(5-bromo-thiophen-2-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 5-(5-bromothien-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil
  参考文献：
  名称：

  Synthesis and in vitro antileishmanial activity of 5-substituted-2′-deoxyuridine derivatives

  摘要：

  We report herein the synthesis and the in vitro antileishmanial evaluation of 5-substituted-2'-deoxyuridine nucleosides. The most active compound against Leishmania donovani promastigotes was Thia-dU (3a) with an IC50 = 3 mu M. This compound exhibited the same activity as zidovudine (3'-azido-2'-deoxythymidine) used as nucleoside reference compound. Considering the cytotoxicity of synthetic compounds on peritoneal murine macrophages., the most toxic compound was MeThio-dU (3d) with a MTC at 10 mu M. Only Methia-dU (3b) was active against intramacrophagic amastigotes with an IC50 = 6.5 mu M. This latter can now be evaluated in vivo, for further investigations through structure-based drug design. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2005.07.001
• 作为产物：
  描述：

  5-iodo-3',5'-di-O-p-toluyl-2'-deoxyuridine 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 溴 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 氯仿 为溶剂， 反应 3.0h， 生成 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[5-(5-bromo-thiophen-2-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication

  摘要：

  2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.

  DOI：

  10.1021/jm00112a011