S-allylthio-6-mercaptopurine riboside

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: S-allylthio-6-mercaptopurine riboside
• 英文别名: S-allylthio-6-mercaptopurine 9-riboside；(2S,3R,4S,5S)-2-(hydroxymethyl)-5-[6-(prop-2-enyldisulfanyl)purin-9-yl]oxolane-3,4-diol
• 化学式: C₁₃H₁₆N₄O₄S₂
• 分子量: 356.426
• InChiKey: UPMVDGSUFKTPMZ-PYSAPBNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  大蒜素 、 6-mercaptopurine riboside 以 乙醇 为溶剂， 反应 4.0h， 以85%的产率得到S-allylthio-6-mercaptopurine riboside
  参考文献：
  名称：

  Novel derivatives of 6-mercaptopurine: Synthesis, characterization and antiproliferative activities of S-allylthio-mercaptopurines

  摘要：

  Biologically active S-allylthio derivatives of 6-mercaptopurine (6-MP) and 6-mercaptopurine riboside (6-MPR) were synthesized. The products, S-allylthio-6-mercaptopurine (SA-6MP) and S-allylthio-6-mercaptopurine riboside (SA-6MPR) were characterized. The antiproliferative activity of the new prodrugs was tested on human leukemia and monolayer cell lines, and compared to that of their parent reactants. The new prodrugs acted by a concentration-dependent mechanism. They inhibited cell proliferation and induced-apoptosis more efficiently than the parent molecules. Leukemia cell lines were more sensitive to the new prodrugs than monolayer cell lines. Higher hydrophobicity of the derivatives improves their penetration into cells, where upon reaction with glutathione, S-allylthioglutathione (GSSA) is formed, and 6-MP or 6-MPR is released for further processing. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.027

文献信息

• WO2008/107873
  申请人：——

  公开号：——

  公开（公告）日：——
• Mercaptopurine derivatives and uses thereof
  申请人：Miron Talia

  公开号：US20100069319A1

  公开（公告）日：2010-03-18

  The invention provides novel mercaptopurine derivatives, e.g., S-allylthio-6-mercaptopurine and S-allylthio-6-mercaptopurine 9-riboside, as well as pharmaceutical compositions thereof. These compounds are highly efficient anti-proliferative agents, thus can be useful for treatment of various diseases or disorders, in particular, proliferative, inflammatory, skin and immune diseases or disorders.
• Novel derivatives of 6-mercaptopurine: Synthesis, characterization and antiproliferative activities of S-allylthio-mercaptopurines
  作者：T. Miron、F. Arditti、L. Konstantinovski、A. Rabinkov、D. Mirelman、A. Berrebi、M. Wilchek

  DOI：10.1016/j.ejmech.2008.03.027

  日期：2009.2

  Biologically active S-allylthio derivatives of 6-mercaptopurine (6-MP) and 6-mercaptopurine riboside (6-MPR) were synthesized. The products, S-allylthio-6-mercaptopurine (SA-6MP) and S-allylthio-6-mercaptopurine riboside (SA-6MPR) were characterized. The antiproliferative activity of the new prodrugs was tested on human leukemia and monolayer cell lines, and compared to that of their parent reactants. The new prodrugs acted by a concentration-dependent mechanism. They inhibited cell proliferation and induced-apoptosis more efficiently than the parent molecules. Leukemia cell lines were more sensitive to the new prodrugs than monolayer cell lines. Higher hydrophobicity of the derivatives improves their penetration into cells, where upon reaction with glutathione, S-allylthioglutathione (GSSA) is formed, and 6-MP or 6-MPR is released for further processing. (C) 2008 Elsevier Masson SAS. All rights reserved.