四氢-1-亚硝基-2(1H)-嘧啶酮 | 62641-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 四氢-1-亚硝基-2(1H)-嘧啶酮
• 英文名称: N-nitrosotetrahydro-2(1H)-pyrimidone
• 英文别名: N-nitrosotetrahydro-2-pyrimidone；1-nitroso-tetrahydro-pyrimidin-2-one；2(1H)-Pyrimidinone, tetrahydro-1-nitroso-；1-nitroso-1,3-diazinan-2-one
• CAS: 62641-66-1
• 化学式: C₄H₇N₃O₂
• mdl: MFCD01688978
• 分子量: 129.118
• InChiKey: UQKPGXYENGNTCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  239.15°C (rough estimate)
• 密度：
  1.3936 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四氢-1-亚硝基-2(1H)-嘧啶酮 在 水 作用下， 生成
  参考文献：
  名称：

  Kawazoe, Yutaka; Kato, Masanari, Heterocycles, 1981, vol. 15, # 2, p. 899 - 904

  摘要：

  DOI：
• 作为产物：
  描述：

  丙烯脲 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 四氢-1-亚硝基-2(1H)-嘧啶酮
  参考文献：
  名称：

  Synthesis of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase

  摘要：

  A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 mu M. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with K-I values ranging between 2 and 11 mu M. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.011

文献信息

• A Novel Route to an Aza Analog of the Marine Natural Product Damirone B
  作者：Oladapo Bakare、Leon H. Zalkow、Edward M. Burgess

  DOI：10.1080/00397919708006095

  日期：1997.5

  Abstract 3-(N-carboalkoxyamino)-1-diazopropane has been used as a difunctional synthon for a three step synthesis of pyrazolo[5,4,3-de]-1,2,3,6,7-pentahydroquinolin-6,7-dione, a tricyclic aza analog of the marine natural product Damirone B.

  摘要 3-(N-carboalkoxyamino)-1-diazopropane 已被用作双功能合成子，用于三步合成吡唑并[5,4,3-de]-1,2,3,6,7-pentahydroquinolin-6， 7-dione，一种海洋天然产物 Damirone B 的三环氮杂类似物。
• Aza-analogues of the marine pyrroloquinoline alkaloids wakayin and tsitsikammamines: Synthesis and topoisomerase inhibition
  作者：Laurent Legentil、Brigitte Lesur、Evelyne Delfourne

  DOI：10.1016/j.bmcl.2005.09.063

  日期：2006.1

  Two aza-analogues of the marine pyrroloquinoline alkaloids wakayin and tsitsikammamines A and B have been synthesized. The strategy used was based on a 1,3-dipolar cycloaddition reaction between indole 4,7-dione and a diazo-aminopropane derivative. One of the two analogues partially inhibits human topoisomerase 1, whereas synthetic intermediates inhibit the enzyme DNA cleavage activity at a concentration comparable to that of the control drug camptothecin. (c) 2005 Elsevier Ltd. All rights reserved.
• Kawazoe, Yutaka; Kato, Masanari, Heterocycles, 1981, vol. 15, # 2, p. 899 - 904
  作者：Kawazoe, Yutaka、Kato, Masanari

  DOI：——

  日期：——
• Synthesis of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase
  作者：Solomon Berhe、Andrew Slupe、Choice Luster、Henry A. Charlier、Don L. Warner、Leon H. Zalkow、Edward M. Burgess、Nkechi M. Enwerem、Oladapo Bakare

  DOI：10.1016/j.bmc.2009.11.011

  日期：2010.1

  A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 mu M. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with K-I values ranging between 2 and 11 mu M. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme. (C) 2009 Elsevier Ltd. All rights reserved.