methyl 5-cyano-1-(β-D-ribofuranosyl)imidazole-4-carboxylate | 1007353-29-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: methyl 5-cyano-1-(β-D-ribofuranosyl)imidazole-4-carboxylate
• 英文别名: methyl 5-cyano-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxylate
• CAS: 1007353-29-8
• 化学式: C₁₁H₁₃N₃O₆
• 分子量: 283.241
• InChiKey: OXDURTKHGLRBLY-PEBGCTIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 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：
  138
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 5-cyano-1-(β-D-ribofuranosyl)imidazole-4-carboxylate 在 肼 作用下， 以 乙醇 为溶剂， 反应 28.0h， 以38%的产率得到7-amino-1-(β-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazin-4-(5H)-one
  参考文献：
  名称：

  Inhibition of Adenosine Deaminase by Analogues of Adenosine and Inosine, Incorporating a Common Heterocyclic Base, 4(7)-Amino-6(5)H-imidazo[4,5-d]pyridazin-7(4)one

  摘要：

  Four nucleoside analogues (1-4) containing a common heterocyclic base, 4(7)-ammo-6(5)H-imidazo[4,5-d]pyridazin-7(4)one, were screened against calf-intestine adenosine deaminase. Compounds I and 3 with K-i values of 10-12 mu M are more than four times as potent inhibitors of ADA compared with 2 and 4, with K-i values of 51-52 mu M. Also, 3 is not a substrate of ADA. Nucleosides 3 and 4 also exhibit moderate in vitro activity against breast cancer cell lines, while all four are only minimally or nontoxic to the normal cells.

  DOI：

  10.1021/jm700931t
• 作为产物：
  描述：

  甲醇 、 ethyl 5-cyano-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate 在 叔丁胺 作用下， 反应 48.0h， 以92%的产率得到methyl 5-cyano-1-(β-D-ribofuranosyl)imidazole-4-carboxylate
  参考文献：
  名称：

  Inhibition of Adenosine Deaminase by Analogues of Adenosine and Inosine, Incorporating a Common Heterocyclic Base, 4(7)-Amino-6(5)H-imidazo[4,5-d]pyridazin-7(4)one

  摘要：

  Four nucleoside analogues (1-4) containing a common heterocyclic base, 4(7)-ammo-6(5)H-imidazo[4,5-d]pyridazin-7(4)one, were screened against calf-intestine adenosine deaminase. Compounds I and 3 with K-i values of 10-12 mu M are more than four times as potent inhibitors of ADA compared with 2 and 4, with K-i values of 51-52 mu M. Also, 3 is not a substrate of ADA. Nucleosides 3 and 4 also exhibit moderate in vitro activity against breast cancer cell lines, while all four are only minimally or nontoxic to the normal cells.

  DOI：

  10.1021/jm700931t

文献信息

• Inhibition of Adenosine Deaminase by Analogues of Adenosine and Inosine, Incorporating a Common Heterocyclic Base, 4(7)-Amino-6(5)<i>H</i>-imidazo[4,5-<i>d</i>]pyridazin-7(4)one
  作者：Ravi K. Ujjinamatada、Pornima Phatak、Angelika M. Burger、Ramachandra S. Hosmane

  DOI：10.1021/jm700931t

  日期：2008.2.1

  Four nucleoside analogues (1-4) containing a common heterocyclic base, 4(7)-ammo-6(5)H-imidazo[4,5-d]pyridazin-7(4)one, were screened against calf-intestine adenosine deaminase. Compounds I and 3 with K-i values of 10-12 mu M are more than four times as potent inhibitors of ADA compared with 2 and 4, with K-i values of 51-52 mu M. Also, 3 is not a substrate of ADA. Nucleosides 3 and 4 also exhibit moderate in vitro activity against breast cancer cell lines, while all four are only minimally or nontoxic to the normal cells.