1-(4-thio-α-D-ribofuranosyl)-cytosine | 161424-58-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(4-thio-α-D-ribofuranosyl)-cytosine
• 英文别名: 4'-α-thiocytidine；4-amino-1-(α-D-4-thio-ribofuranosyl)-1H-pyrimidin-2-one；1-<4-Thio-α-D-ribofuranosyl>-cytosin
• CAS: 161424-58-4
• 化学式: C₉H₁₃N₃O₄S
• 分子量: 259.286
• InChiKey: GAKJJSAXUFZQTL-JBBNEOJLSA-N

物化性质

• 沸点：
  535.0±60.0 °C(predicted)
• 密度：
  1.90±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.85
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  121.6
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1-(4-thio-α-D-ribofuranosyl)-N4-benzoyl-cytosine 在 甲醇 、 氨 作用下， 反应 24.0h， 以72%的产率得到1-(4-thio-α-D-ribofuranosyl)-cytosine
  参考文献：
  名称：

  A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation

  摘要：

  A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor ($) under bar 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the a and beta anomers of 4'-thioadenosine and 4'-thiocytidine, respectively. 4'-thio-beta-($) under bar D-adenosine, ($) under bar 12 beta, is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.

  DOI：

  10.1080/15257779408013205

文献信息

• Nucleosides and Nucleotides. 232. Synthesis of 2′-<i>C</i>-Methyl-4′-thiocytidine: Unexpected Anomerization of the 2′-Keto-4′-thionucleoside Precursor
  作者：Daisuke Kaga、Noriaki Minakawa、Akira Matsuda

  DOI：10.1080/15257770500267204

  日期：2005.9.1

  The synthesis of 2′-C-methyl-4′-thiocytidine (16) is described. Since the 2′-keto-4′-thiocytidine derivative 2β unexpectedly isomerized to 2α and the methylation of 2β proceeded predominantly from the less hindered α-face to give 7, the desired product 16 was synthesized via the Pummerer reaction of the sulfoxide 14 and N 4 -benzoylcytosine.

  描述了 2'-C-甲基-4'-硫胞苷 (16) 的合成。由于 2'-酮基-4'-硫胞苷衍生物 2β 出乎意料地异构化为 2α 并且 2β 的甲基化主要从受阻较小的 α 面进行得到 7，因此通过亚砜 14 和N 4 -苯甲酰胞嘧啶。