N-(5,6-dichloro-3-nitropyrazinyl)acetamide | 87155-52-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5,6-dichloro-3-nitropyrazinyl)acetamide
• 英文别名: N-(5,6-dichloro-3-nitropyrazin-2-yl)acetamide
• CAS: 87155-52-0
• 化学式: C₆H₄Cl₂N₄O₃
• 分子量: 251.029
• InChiKey: MUBLVGCVHFUEOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(5,6-dichloro-3-nitropyrazinyl)acetamide 、 3-氨基巴豆酸乙酯 在 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以42%的产率得到
  参考文献：
  名称：

  Nucleophilic aromatic substitution by 3-amino-2-butenoates

  摘要：

  DOI：

  10.1021/jo00170a053
• 作为产物：
  描述：

  5,6-dichloro-3-nitropyrazinamine 在 碳酸氢钠 作用下， 以 乙酰氯 为溶剂， 生成 N-(5,6-dichloro-3-nitropyrazinyl)acetamide
  参考文献：
  名称：

  N-Acyl derivatives of 6-alkylamino 5-chloro-3-nitropyrazinamines for

  摘要：

  本文披露了6-(烷基氨基)-5-氯-3-硝基吡嗪胺的N-酰基衍生物具有增加肿瘤细胞对辐射敏感性的活性。还披露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。

  公开号：

  US04414215A1

文献信息

• Amino and alkylaminoalkenoate ester derivatives of
  申请人：Merck & Co., Inc.

  公开号：US04435400A1

  公开（公告）日：1984-03-06

  The present invention relates to aminoalkenoate ester derivatives of 2-amino-5-chloro-3-nitropyrazine useful as sensitizers of hypoxic tumor cells to therapeutic radiation. It also relates to the process of preparing such compounds by reaction of 2-amino-5,6-dichloro-3-nitro-pyrazine with an amino or alkylamino substituted .alpha.,.beta.-unsaturated alkenoate ester. In addition the application relates to pharmaceutical compositions containing such compounds and to methods of treatment comprising administering such compounds to patients undergoing radiation treatment to enhance the effectiveness of such treatment by sensitizing hypoxic tumor cells to therapeutic radiation.

  本发明涉及2-氨基-5-氯-3-硝基吡嗪的氨基烯酸酯衍生物，其可作为低氧肿瘤细胞对治疗放射线的敏感剂。还涉及通过将2-氨基-5,6-二氯-3-硝基吡嗪与氨基或烷基氨基取代的α，β-不饱和烯酸酯反应制备这种化合物的方法。此外，本申请还涉及含有这种化合物的制药组合物和治疗方法，包括将这种化合物用于接受放射治疗的患者，以增强这种治疗的有效性，通过使低氧肿瘤细胞对治疗放射线敏感。
• Amino and amido derivatives of chloro nitro amino and alkylamino pyrazines useful as adjuncts to radiation therapy
  申请人：Merck & Co., Inc.

  公开号：EP0096125A1

  公开（公告）日：1983-12-21

  2-Substituted amino derivatives of 6-amino-3-chloro-5-nitropyrazin-2-yl are prepared by converting 3-amino-5,6-dichloropyrazinecarboxylic acid to 5,6-dichloro-3-nitropyrazinamine and treating said compound with an amine to produce the corresponding 2-substituted amino compound. 2,6-Di(alkylamino) derivatives of chloronitropyrazines are prepared from dichloronitropyrazinamine by diazotization of the amine followed by halogen exchange to produce an intermediate dichloro-halo nitropyrazine followed by reaction with one or two motes of an alkyl amine to effect replacement of one or two of the pyrazine halogens. N-acyl derivatives of 6-lalkylamino)-5-chloro-3-nitro- pyrazinamines are prepared by treatment of 5,6-dichloro-3-nitropyrazinamine with an acylating agent to produce the corresponding acylated pyrazinamine followed by treatment of said acylate dpyrazinamine with a lower alkylamine to replace one of the chloro substituents and produce a 2-acylamino-6-(alkylamino)-5-chloro-3-nitro pyrazinamine.

  通过将 3-氨基-5,6-二氯吡嗪羧酸转化为 5,6-二氯-3-硝基吡嗪胺，并用胺处理上述化合物以生成相应的 2-取代氨基化合物，制备 6-氨基-3-氯-5-硝基吡嗪-2-基的 2-取代氨基衍生物。 2,6-二(烷基氨基)氯代硝基吡嗪衍生物是由二氯硝基吡嗪胺制备的，方法是将胺重氮化，然后进行卤素交换，生成中间体二氯卤代硝基吡嗪，再与一或两个烷基胺反应，以实现吡嗪卤素的一或两个置换。 6-烷基氨基）-5-氯-3-硝基吡嗪胺的 N-酰基衍生物的制备方法是用酰化剂处理 5,6-二氯-3-硝基吡嗪胺，生成相应的酰化吡嗪胺，然后用低级烷基胺处理所述酰化吡嗪胺，以取代其中一个氯取代基，生成 2-酰氨基-6-（烷基氨基）-5-氯-3-硝基吡嗪胺。
• Hartman, George D.; Hartman, Richard D., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1089 - 1092
  作者：Hartman, George D.、Hartman, Richard D.

  DOI：——

  日期：——
• 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.;HARTMAN, R. D., J. HETEROCYCL. CHEM., 1983, 20, N 4, 1089-1091
  作者：HARTMAN, G. D.、HARTMAN, R. D.

  DOI：——

  日期：——