1-(3-C-azidomethyl-β-D-ribofuranosyl)cytosine | 1239479-29-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3-C-azidomethyl-β-D-ribofuranosyl)cytosine
• 英文别名: 4-amino-1-[(2R,3R,4S,5R)-4-(azidomethyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 1239479-29-8
• 化学式: C₁₀H₁₄N₆O₅
• 分子量: 298.258
• InChiKey: PKXNQBUCYDEQBI-AMCGLFBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(3-C-azidomethyl-2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-N4-benzoylcytosine 在 甲醇 、 氨 作用下， 以77%的产率得到1-(3-C-azidomethyl-β-D-ribofuranosyl)cytosine
  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.