1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl-4-carboxymethyl)thymine | 1030384-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl-4-carboxymethyl)thymine
• 英文别名: methyl (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-carboxylate；methyl (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-2-carboxylate
• CAS: 1030384-66-7
• 化学式: C₁₁H₁₃N₅O₅
• 分子量: 295.255
• InChiKey: GNMODFGGJMZGRW-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl-4-carboxymethyl)thymine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以95%的产率得到methyl (2S,3S,5R)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-2-carboxylate
  参考文献：
  名称：

  Nucleoside derived amino acids (NDA) in foldamer chemistry: synthesis and conformational studies of homooligomers of modified AZT

  摘要：

  Homo short-oligomers of a novel trans-beta-amino acid derived from AZT were synthesized and characterized. These adopt right-handed helical turns with their bases positioned systematically along the helix axis. These studies open up new possibilities for synthesizing nucleoside derived functional foldamers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.001
• 作为产物：
  描述：

  甲醇 、 3'-azido-3'-deoxy-thymidine-5'-carboxylic acid 在 硫酸 作用下， 反应 5.0h， 以61%的产率得到1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl-4-carboxymethyl)thymine
  参考文献：
  名称：

  4′-Substituted pyrimidine nucleosides lacking 5′-hydroxyl function as potential anti-HCV agents

  摘要：

  Hepatitis C virus (HCV) infection is one of the major health problems worldwide. If left untreated, it leads to liver cirrhosis, liver cancer and death. Herein, we report synthesis and anti-HCV activity of a new class of pyrimidine nucleosides possessing a 4'-carboxymethyl (9-16, 21 and 23) or 4'-carboxamide function (17-19 and 24). Among these, 10-12 (EC50 = 33.1-42.4 mu M), 14 and 21 (EC50 = 43.4-59.5 mu M) exhibited potent activity in HCV-1a replicon cells without any toxicity to parent Huh-7 cells (CC50 = > 829-1055 mu M). The anti-HCV activities demonstrated by this unusual class of compounds were superior to that of ribavirin (EC50 = 81.9 lM). Further, the most active analog, 12, was found to interact synergistically with ribavirin to inhibit HCV RNA replication. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.024

文献信息

• Nucleoside derived amino acids (NDA) in foldamer chemistry: synthesis and conformational studies of homooligomers of modified AZT
  作者：S. Chandrasekhar、G. Pavan Kumar Reddy、M. Udaya Kiran、Ch. Nagesh、B. Jagadeesh

  DOI：10.1016/j.tetlet.2008.03.001

  日期：2008.4

  Homo short-oligomers of a novel trans-beta-amino acid derived from AZT were synthesized and characterized. These adopt right-handed helical turns with their bases positioned systematically along the helix axis. These studies open up new possibilities for synthesizing nucleoside derived functional foldamers. (C) 2008 Elsevier Ltd. All rights reserved.
• 4′-Substituted pyrimidine nucleosides lacking 5′-hydroxyl function as potential anti-HCV agents
  作者：Neeraj Shakya、Satish Vedi、Chao Liang、Fang Yang、Babita Agrawal、Rakesh Kumar

  DOI：10.1016/j.bmcl.2014.01.024

  日期：2014.3

  Hepatitis C virus (HCV) infection is one of the major health problems worldwide. If left untreated, it leads to liver cirrhosis, liver cancer and death. Herein, we report synthesis and anti-HCV activity of a new class of pyrimidine nucleosides possessing a 4'-carboxymethyl (9-16, 21 and 23) or 4'-carboxamide function (17-19 and 24). Among these, 10-12 (EC50 = 33.1-42.4 mu M), 14 and 21 (EC50 = 43.4-59.5 mu M) exhibited potent activity in HCV-1a replicon cells without any toxicity to parent Huh-7 cells (CC50 = > 829-1055 mu M). The anti-HCV activities demonstrated by this unusual class of compounds were superior to that of ribavirin (EC50 = 81.9 lM). Further, the most active analog, 12, was found to interact synergistically with ribavirin to inhibit HCV RNA replication. (C) 2014 Published by Elsevier Ltd.