5-carbamimodoyl-1-(β-D-ribofuranosyl)-1H-imidazole-4-carbohydrazide | 1007353-31-2

• 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: 5-carbamimodoyl-1-(β-D-ribofuranosyl)-1H-imidazole-4-carbohydrazide
• 英文别名: Carbohydrazonamide derivative, 11；N'-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydrazinecarbonyl)imidazole-4-carboximidamide
• CAS: 1007353-31-2
• 化学式: C₁₀H₁₇N₇O₅
• 分子量: 315.289
• InChiKey: KPJFGMVACWBPRG-KAFVXXCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  207
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 5-cyano-1-(β-D-ribofuranosyl)imidazole-4-carboxylate 在 sodium methylate 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 75.5h， 以54%的产率得到5-carbamimodoyl-1-(β-D-ribofuranosyl)-1H-imidazole-4-carbohydrazide
  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.