9-(3-C-azidomethyl-β-D-ribofuranosyl)adenine | 1239479-25-4

• 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-azidomethyl-β-D-ribofuranosyl)adenine
• 英文别名: (2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-(azidomethyl)-2-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-(azidomethyl)-2-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1239479-25-4
• 化学式: C₁₁H₁₄N₈O₄
• 分子量: 322.283
• InChiKey: XBICOYSFCXUKHR-ZGUVBZSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9-(3-C-azidomethyl-β-D-ribofuranosyl)adenine 在 水 、 溶剂黄146 、 sodium nitrite 作用下， 反应 2.5h， 以48%的产率得到9-(3-C-azidomethyl-β-D-ribofuranosyl)hypoxanthine
  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
• 作为产物：
  描述：

  9-(3-C-azidomethyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl)-6-chloropurine 在 sodium periodate 、 ruthenium(III) trichloride hydrate 、 甲醇 、 氨 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 48.0h， 以28 mg的产率得到9-(3-C-azidomethyl-β-D-ribofuranosyl)adenine
  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.