9-(3-C-fluoromethyl-β-D-ribofuranosyl)-N6-methyladenine | 1239479-23-2

• 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: 9-(3-C-fluoromethyl-β-D-ribofuranosyl)-N6-methyladenine
• 英文别名: (2R,3S,4R,5R)-3-(fluoromethyl)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]tetrahydrofuran-3,4-diol；(2R,3S,4R,5R)-3-(fluoromethyl)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolane-3,4-diol
• CAS: 1239479-23-2
• 化学式: C₁₂H₁₆FN₅O₄
• 分子量: 313.289
• InChiKey: JRRNCPGXIRKXGQ-WHNOBIIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  9-(3-C-fluoromethyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-N6-methyladenine 在 甲酸 、 钯 作用下， 以 甲醇 为溶剂， 以79%的产率得到9-(3-C-fluoromethyl-β-D-ribofuranosyl)-N6-methyladenine
  参考文献：
  名称：

  Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C-substituted-methyl pyrimidine and purine nucleosides

  摘要：

  On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N-3, or F) at the 3'-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.002

文献信息

• Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C-substituted-methyl pyrimidine and purine nucleosides
  作者：Won Jun Choi、Yu Min Kim、Hea Ok Kim、Hyuk Woo Lee、Dong-Eun Kim、Kwang-su Park、Youhoon Chong、Lak Shin Jeong

  DOI：10.1016/j.bmc.2010.05.002

  日期：2010.7

  On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N-3, or F) at the 3'-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.