methyl 6-chloro-3-nitropyrazinoate | 89690-75-5

• 物质功能分类: 医药中间体
• 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-chloro-3-nitropyrazinoate
• 英文别名: Methyl-6-chloro-3-nitropyrazinoate；Methyl 6-chloro-3-nitropyrazine-2-carboxylate
• CAS: 89690-75-5
• 化学式: C₆H₄ClN₃O₄
• 分子量: 217.568
• InChiKey: NJSDJWJVROOPIK-UHFFFAOYSA-N

物化性质

• 沸点：
  343.2±37.0 °C(Predicted)
• 密度：
  1.581±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-氨基-1,2-丙二醇 、 methyl 6-chloro-3-nitropyrazinoate 在 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以60%的产率得到methyl 6-(2,3-dihydroxypropyl)amino-3-nitropyrazinoate
  参考文献：
  名称：

  Synthesis and activity of novel nitropyrazines for use as hypoxic cell radiosensitizers

  摘要：

  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.

  DOI：

  10.1021/jm00378a018
• 作为产物：
  描述：

  S,S-dimethyl-N-(5-chloro-3-carbomethoxypyrazin-2-yl)sulfilimine 在 臭氧 、 间氯过氧苯甲酸 作用下， 生成 methyl 6-chloro-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

• Novel pyrazine derivatives or salts thereof, pharmaceutical composition containing the same, and production intermediates thereof
  申请人：Toyama Chemical Co., Ltd.

  公开号：US20030130213A1

  公开（公告）日：2003-07-10

  Pyrazine derivatives represented by general formula [1]: 1 wherein the variables are as defined in the specification, or salts thereof have an excellent antiviral activity and are useful as a therapeutic agent for treating viral infections. Further, fluoropyrazine-carboxamide derivatives represented by general formula [2]: 2 wherein the variables are as defined in the specification, or salts thereof are useful as an intermediate for production of the compounds of general formula [1], and as an intermediate for production of the fluoropyrazine-carboxamide derivatives of which one typical example is 6-fluoro-3-hyroxy-2-pyrazine-carboxamide having an antiviral activity.

  具有通式[1]所示的吡嗪衍生物及其盐，其中变量如说明书中所定义，具有优异的抗病毒活性，可作为治疗病毒感染的治疗剂。此外，具有通式[2]所示的氟吡嗪-酰胺衍生物及其盐，其中变量如说明书中所定义，可作为制备通式[1]化合物的中介体，以及作为制备具有抗病毒活性的氟吡嗪-酰胺衍生物的中介体，其中一个典型例子是具有抗病毒活性的6-氟-3-羟基-2-吡嗪酰胺。
• Nucleophilic substitution by 3-amino-1,2-propanediol in nitropyrazines and nitroquinoxalines
  作者：George D. Hartman、John E. Schwering

  DOI：10.1002/jhet.5570200419

  日期：1983.7

  Treatment of 2-chloro-3-nitropyrazine and 2-chloro-5-nitropyrazine with 3-amino-1, 2-propanediol affords products derived from displacement of chloride, while similar reaction of methyl 3-nitropyrazinoate and 2-chloro-3-nitroquinoxaline gives clean nitro group replacement. Analogous reaction of methyl 6-chloro-3-nitropyrazinoate affords a mixture containing products derived from competitive displacement

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

  公开号：US04609659A1

  公开（公告）日：1986-09-02

  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.

  本发明揭示了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。还揭示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。
• Pyrazine derivatives or salts thereof, pharmaceutical composition containing the same, and production intermediates thereof
  申请人：Toyama Chemical Co., Ltd.

  公开号：US06800629B2

  公开（公告）日：2004-10-05

  Pyrazine derivatives represented by general formula [1]: wherein the variables are as defined in the specification, or salts thereof have an excellent antiviral activity and are useful as a therapeutic agent for treating viral infections. Further, fluoropyrazine-carboxamide derivatives represented by general formula [2]: wherein the variables are as defined in the specification, or salts thereof are useful as an intermediate for production of the compounds of general formula [1], and as an intermediate for production of the fluoropyrazine-carboxamide derivatives of which one typical example is 6-fluoro-3-hyroxy-2-pyrazine-carboxamide having an antiviral activity.

  一般式[1]所表示的吡嗪衍生物：其中变量如规范中所定义，或其盐具有优异的抗病毒活性，可用作治疗病毒感染的治疗剂。此外，一般式[2]所表示的氟吡嗪羧酰胺衍生物：其中变量如规范中所定义，或其盐，可用作一般式[1]化合物的生产中间体，以及用作生产氟吡嗪羧酰胺衍生物的中间体，其中一个典型例子是具有抗病毒活性的6-氟-3-羟基-2-吡嗪羧酰胺。
• 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。