2-chloro-4'-thio-2'-O-<1-imidazolyl(thiocarbonyl)>-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine | 169514-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-chloro-4'-thio-2'-O-<1-imidazolyl(thiocarbonyl)>-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine
• CAS: 169514-83-4
• 化学式: C₂₆H₄₀ClN₇O₄S₂Si₂
• 分子量: 670.404
• InChiKey: RGYLGYIQLKEKAD-UMCMBGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  42.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  124.36
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2-chloro-4'-thio-2'-O-<1-imidazolyl(thiocarbonyl)>-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 在 偶氮二异丁腈 、 三正丁基氢锡 、 四乙基氟化铵水合物 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 1.05h， 生成 2-chloro-2'-deoxy-4'-thioadenosine
  参考文献：
  名称：

  Synthesis and Biological Activity of 4′-Thionucleosides of 2-Chloroadenine¹

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-D-ribofuranose,prepared from 2,3,5-tri-O-benzyl-D-ribofuranose in four steps, was converted to the corresponding 2-chloroadenine nucleoside (8), which was deoxygenated to obtain 2-chloro-2'-deoxy-4'-thioadenosine (12). This is the first report of a 2'-deoxy-4'-thioribonucleoside of a purine rather than a pyrimidine. These novel nucleosides (8 and 12) were cytotoxic to several human tumor cell lines in culture.

  DOI：

  10.1080/15257779408009484
• 作为产物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 以 吡啶 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-chloro-4'-thio-2'-O-<1-imidazolyl(thiocarbonyl)>-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine
  参考文献：
  名称：

  Synthesis and Biological Activity of 4′-Thionucleosides of 2-Chloroadenine¹

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-D-ribofuranose,prepared from 2,3,5-tri-O-benzyl-D-ribofuranose in four steps, was converted to the corresponding 2-chloroadenine nucleoside (8), which was deoxygenated to obtain 2-chloro-2'-deoxy-4'-thioadenosine (12). This is the first report of a 2'-deoxy-4'-thioribonucleoside of a purine rather than a pyrimidine. These novel nucleosides (8 and 12) were cytotoxic to several human tumor cell lines in culture.

  DOI：

  10.1080/15257779408009484

文献信息

• The Synthesis and Biological Activity of Certain 4'-Thionucleosides
  作者：John Secrist、William Parker、Kamal Tiwari、Lea Messini、Sue Shaddix、Lucy Rose、L. Lee Bennett、John Montgomery

  DOI：10.1080/15257779508012449

  日期：1995.5.1

  Abstract Results are presented on the synthesis and biological activity of several types of 4′-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4′-thiothymidine are also presented.

  摘要介绍了几种类型的4'-硫代核苷作为潜在抗癌剂的合成和生物学活性。还介绍了有关4'-硫代胸苷的作用机理的详细研究。