1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(5-methyl-1,3-thiazol-2-yl)pyrimidine-2,4-dione

• 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-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(5-methyl-1,3-thiazol-2-yl)pyrimidine-2,4-dione
• 化学式: C₁₃H₁₅N₃O₅S
• 分子量: 325.345
• InChiKey: QOPSYYBMTNSLHJ-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3',5'-双乙酰基-5-碘-脱氧尿苷 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(5-methyl-1,3-thiazol-2-yl)pyrimidine-2,4-dione
  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

文献信息

• Synthesis and in vitro antileishmanial activity of 5-substituted-2′-deoxyuridine derivatives
  作者：Corinne Peyron、Rachid Benhida、Christian Bories、Philippe M. Loiseau

  DOI：10.1016/j.bioorg.2005.07.001

  日期：2005.12

  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.