7-Imino-1,3,6,8-tetraaza-spiro[4.4]nonane-2,4,9-trione | 480996-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 7-Imino-1,3,6,8-tetraaza-spiro[4.4]nonane-2,4,9-trione
• 英文别名: Spiroiminodihydantoin；2-amino-1,3,6,8-tetrazaspiro[4.4]non-1-ene-4,7,9-trione
• CAS: 480996-13-2
• 化学式: C₅H₅N₅O₃
• 分子量: 183.126
• InChiKey: HJWQNCPSKFANJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2-Amino-4-hydroxy-5-oxo-4,5-dihydro-3H-imidazole-4-carbonyl)-urea 在 三氟乙酸酐 作用下， 反应 5.0h， 生成 7-Imino-1,3,6,8-tetraaza-spiro[4.4]nonane-2,4,9-trione
  参考文献：
  名称：

  Characterization of Spiroiminodihydantoin as a Product of One-Electron Oxidation of 8-Oxo-7,8-dihydroguanosine

  摘要：

  [GRAPHICS]Further oxidation of the common DNA lesion 8-oxo-7,8-dihydroguanosine by one-electron oxidants such as IrCl62-, Fe(CN)(6)(3-), or SO4- leads to two major products, depending upon reaction conditions. In nucleosides at pH 7, 22 degrees C, the principal product is shown herein to be a spiroiminodihydantoin nucleoside, as a diastereomeric mixture, that can be characterized by NMR, ESI-MS/MS, and independent synthesis.

  DOI：

  10.1021/ol9913643

文献信息

• Spirodihydantoin Is a Minor Product of 5-Hydroxyisourate in Urate Oxidation
  作者：Hongbin Yu、Jacquin C. Niles、John S. Wishnok、Steven R. Tannenbaum

  DOI：10.1021/ol048547w

  日期：2004.9.1

  Spirodihydantoin is a minor product from oxidation of uric acid (similar to0.15% yield), while spiroiminodihydantoin is a major product from oxidation of 8-oxo-7,8-dihydroguanine (37% yield, pH 10.2). High pH and temperature favor the formation of both spiro compounds. O-18 labeling experiments and in situ generation and decomposition of 5-hydroxy-N7-methylisouric acid indicate that spirodihydantoin and allantoin and spiroiminodihydantoin and guanidinohydantoin are products of 5-hydroxyisourate and 5-hydroxy-8-oxo-7,8-dihydroguanine intermediates, respectively.
• Characterization of Spiroiminodihydantoin as a Product of One-Electron Oxidation of 8-Oxo-7,8-dihydroguanosine
  作者：Wenchen Luo、James G. Muller、Elliot M. Rachlin、Cynthia J. Burrows

  DOI：10.1021/ol9913643

  日期：2000.3.1

  [GRAPHICS]Further oxidation of the common DNA lesion 8-oxo-7,8-dihydroguanosine by one-electron oxidants such as IrCl62-, Fe(CN)(6)(3-), or SO4- leads to two major products, depending upon reaction conditions. In nucleosides at pH 7, 22 degrees C, the principal product is shown herein to be a spiroiminodihydantoin nucleoside, as a diastereomeric mixture, that can be characterized by NMR, ESI-MS/MS, and independent synthesis.