methyl 6-(2,3-dihydroxypropyl)amino-3-nitropyrazinoate | 87885-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl 6-(2,3-dihydroxypropyl)amino-3-nitropyrazinoate
• 英文别名: Pyrazinecarboxylic acid, 6-[(2,3-dihydroxypropyl；methyl 6-(2,3-dihydroxypropylamino)-3-nitropyrazine-2-carboxylate
• CAS: 87885-53-8
• 化学式: C₉H₁₂N₄O₆
• 分子量: 272.217
• InChiKey: LQIAEAOIFUAQMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  107-109 °C
• 沸点：
  597.1±50.0 °C(Predicted)
• 密度：
  1.569±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  S,S-dimethyl-N-(5-chloro-3-carbomethoxypyrazin-2-yl)sulfilimine 在 臭氧 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 异丙醇 为溶剂， 反应 16.67h， 生成 methyl 6-(2,3-dihydroxypropyl)amino-3-nitropyrazinoate
  参考文献：
  名称：

  在硝基吡嗪和硝基喹喔啉中用3-氨基-1,2-丙二醇进行亲核取代

  摘要：

  用3-氨基-1，2-丙二醇处理2-氯-3-硝基吡嗪和2-氯-5-硝基吡嗪，得到的产物是氯化物的取代，而3-硝基吡嗪酸甲酯和2-氯-3-的类似反应硝基喹喔啉可提供干净的硝基取代基。6-氯-3-硝基吡嗪酸甲酯的类似反应提供了一种混合物，该混合物含有竞争性取代氯化物和亚硝酸盐的产物。

  DOI：

  10.1002/jhet.5570200419

文献信息

• 2,6-disubstituted derivatives of 3-nitropyrazines useful as adjuncts to
  申请人：Merck & Co., Inc.

  公开号：US04709035A1

  公开（公告）日：1987-11-24

  2,6-Disubstituted derivatives of 3-nitropyrazine are disclosed to have activity in increasing the sensitivity of tumor cells to radiation. Also disclosed are methods of preparing such compounds and pharmaceutical compositions including such compounds.

  公开了3-硝基吡嗪的2,6-二取代衍生物具有增加肿瘤细胞对辐射敏感性的活性。还公开了制备这种化合物的方法和包括这种化合物的制药组合物。
• Substituted nitropyrazine compounds, process for their preparation and pharmaceutical compositions containing them
  申请人：Merck & Co., Inc.

  公开号：EP0111151A1

  公开（公告）日：1984-06-20

  2 or 6 substituted and 2, 6-disubstituted derivatives of 3-nitropyrazine and processes for their preparation are disclosed. Said derivatives have an activity in increasing the sensitivity of tumor cells to radiation. Also disclosed are pharmaceutical compositions containing said derivatives as active ingredients.

  本研究公开了 3-硝基吡嗪的 2 或 6 取代和 2，6-二取代衍生物及其制备方法。所述衍生物具有增加肿瘤细胞对辐射敏感性的活性。还公开了含有上述衍生物作为活性成分的药物组合物。
• Synthesis and activity of novel nitropyrazines for use as hypoxic cell radiosensitizers
  作者：George D. Hartman、Richard D. Hartman、John E. Schwering、Nigel R. Jones、Peter Wardman、Margaret E. Watts、Michael Woodcock

  DOI：10.1021/jm00378a018

  日期：1984.12

  A series of eight novel nitropyrazines has been prepared by oxidation of sulfoximine intermediates. The partition coefficient, one-electron reduction potential, sensitizer enhancement ratio, and chronic and acute aerobic cytotoxicity have been measured for each. Two representatives of this series were tested in the Ames test and were not found to be mutagenic.
• HARTMAN, G. D.;SCHWERING, J. E., J. HETEROCYCL. CHEM., 1983, 20, N 4, 947-950
  作者：HARTMAN, G. D.、SCHWERING, J. E.

  DOI：——

  日期：——
• HARTMAN, G. D.;HARTMAN, R. D.;SCHWERING, J. E.;SAARI, W. S.;ENGELHARDT, E+, J. MED. CHEM., 1984, 27, N 12, 1634-1639
  作者：HARTMAN, G. D.、HARTMAN, R. D.、SCHWERING, J. E.、SAARI, W. S.、ENGELHARDT, E+

  DOI：——

  日期：——