5-Amino-4-iminoallantoin | 133364-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 5-Amino-4-iminoallantoin
• 英文别名: (4-amino-5-imino-2-oxo-imidazolidin-4-yl)-urea；(4-Amino-5-imino-2-oxo-imidazolidin-4-yl)-harnstoff；(4,5-Diamino-2,5-dihydro-2-oxo-1H-imidazol-5-yl)urea；(4-amino-5-imino-2-oxoimidazolidin-4-yl)urea
• CAS: 133364-42-8
• 化学式: C₄H₈N₆O₂
• 分子量: 172.147
• InChiKey: GYWFAACISAKPMW-UHFFFAOYSA-N

物化性质

• 熔点：
  295 °C (decomp)
• 密度：
  2.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Amino-4-iminoallantoin 在 ammonium hydroxide 作用下， 反应 5.0h， 以80%的产率得到cis-1,5-diamino-2,4,6,8-tetraazabicyclo-<3.3.0>octane-3,7-dione
  参考文献：
  名称：

  脱氢-4-亚氨基丙氨酸及其共价加合物的合成与结构

  摘要：

  显示两个连续的Denicke反应产物的表示是不正确的。铁氰化物在氨水中氧化尿酸（1a）得到5-氨基-4-亚氨基丙氨酸（4）和1,5-二氨基-3,7-二氧代-2,4,6,8-四氮杂双环[3.3.0]辛烷（5a），而甲基化尿酸1b-g仅提供相应的终产物5。当初级加合物4暴露于稀乙酸中时，产生关键的脱氢-4-亚氨基丙氨酸（6）。通过用碘氧化1-亚氨基丙氨酸（2）提供了一条通往6的直接途径。脱氢丙氨酸（8）及其4-亚氨基类似物6在5位形成共价加合物（例如与MeOH）。简要介绍了反应的逐步性质和区域化学过程的基本原理。

  DOI：

  10.1016/s0040-4020(01)80927-3
• 作为产物：
  描述：

  Diaminooxalyldiureid 在 ammonium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 生成 5-Amino-4-iminoallantoin
  参考文献：
  名称：

  脱氢-4-亚氨基丙氨酸及其共价加合物的合成与结构

  摘要：

  显示两个连续的Denicke反应产物的表示是不正确的。铁氰化物在氨水中氧化尿酸（1a）得到5-氨基-4-亚氨基丙氨酸（4）和1,5-二氨基-3,7-二氧代-2,4,6,8-四氮杂双环[3.3.0]辛烷（5a），而甲基化尿酸1b-g仅提供相应的终产物5。当初级加合物4暴露于稀乙酸中时，产生关键的脱氢-4-亚氨基丙氨酸（6）。通过用碘氧化1-亚氨基丙氨酸（2）提供了一条通往6的直接途径。脱氢丙氨酸（8）及其4-亚氨基类似物6在5位形成共价加合物（例如与MeOH）。简要介绍了反应的逐步性质和区域化学过程的基本原理。

  DOI：

  10.1016/s0040-4020(01)80927-3

文献信息

• Aging Lowers Steady-State Antioxidant Enzyme and Stress Protein Expression in Primary Hepatocytes
  作者：D. M. Hall、G. L. Sattler、C. A. Sattler、H. J. Zhang、L. W. Oberley、H. C. Pitot、K. C. Kregel

  DOI：10.1093/gerona/56.6.b259

  日期：2001.6.1

  It has been reported that the isolation and culture of primary hepatocytes can compromise cellular ability to constituitively express antioxidant enzyme (AE) genes, making it difficult to study their regulation ex vivo. In the present study, the steady-state expression of manganese-containing superoxide dismutase, copper- and zinc-containing superoxide dismutase, catalase, and glutathione peroxidase was assessed in primary hepatocytes isolated from young and senescent rats and cultured in Matrigel. There was no change in steady-state superoxide dismutase protein or activity levels in cells collected from young animals and cultured for 7 days. Catalase expression was initially increased, and then it declined 30%. In contrast, superoxide dismutase expression declined 60% and catalase expression declined 50% in cells from senescent animals. Constitutive and inducible 70-kDa heat shock protein expression increased coincident with declining AE levels in the young cells but not senescent cells. For both age groups, electron micrographs showed rounded hepatocytes with abundant rough endoplasmic reticulum, mitochondria, and peroxisomes. Hepatocytes were organized into clusters of 6-12 cells surrounding a large central lumen devoid of microvilli. Each cluster also contained smaller microvilli-lined lumens between adjacent hepatocytes that resembled canniculi. The plasma membranes of these lumens were sealed from the extracellular space by junctional complexes. Gap junctions in the plasma membrane suggest that hepatocytes were capable of intercellular communication. We conclude that the Matrigel system can be used to study AE regulation in primary hepatocytes from young and senescent animals, provided that experiments can be conducted within a time frame of 5-7 days in culture. These data also support the hypothesis that aging compromises hepatocellular ability to maintain AE status and upregulate stress protein expression.
• POPOVIC, T.;SOKOLIC, LEA;MODRIC, NEVENKA;PALKOVIC, A.;POJE, M., TETRAHEDRON, 47,(1991) N, C. 317-322
  作者：POPOVIC, T.、SOKOLIC, LEA、MODRIC, NEVENKA、PALKOVIC, A.、POJE, M.

  DOI：——

  日期：——
• Synthesis and structure of dehydro-4-iminoallantoin and its covalent adducts
  作者：T. Popović、Lea Sokolić、Nevenka Modrić、A. Palković、M. Poje

  DOI：10.1016/s0040-4020(01)80927-3

  日期：1991.1

  (6) arose on exposure of the primary adduct 4 to dilute acetic acid; a direct route to 6 was provided by oxidation of 1-iminoallantoin (2) with iodine. Both dehydro-allantoin (8) and its 4-imino analogue 6 form covalent adducts (e.g. with MeOH) at the 5-position. A brief rationale which focusses upon the stepwise nature and regiochemical course of the reaction is presented.

  显示两个连续的Denicke反应产物的表示是不正确的。铁氰化物在氨水中氧化尿酸（1a）得到5-氨基-4-亚氨基丙氨酸（4）和1,5-二氨基-3,7-二氧代-2,4,6,8-四氮杂双环[3.3.0]辛烷（5a），而甲基化尿酸1b-g仅提供相应的终产物5。当初级加合物4暴露于稀乙酸中时，产生关键的脱氢-4-亚氨基丙氨酸（6）。通过用碘氧化1-亚氨基丙氨酸（2）提供了一条通往6的直接途径。脱氢丙氨酸（8）及其4-亚氨基类似物6在5位形成共价加合物（例如与MeOH）。简要介绍了反应的逐步性质和区域化学过程的基本原理。