2-(2-Bromo-ethyl)-5-butyl-4,6-dimethyl-5H-pyrrolo[3,4-c]pyrrole-1,3-dione | 151722-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(2-Bromo-ethyl)-5-butyl-4,6-dimethyl-5H-pyrrolo[3,4-c]pyrrole-1,3-dione
• 英文别名: 5-(2-Bromoethyl)-2-butyl-1,3-dimethylpyrrolo[3,4-c]pyrrole-4,6-dione
• CAS: 151722-62-2
• 化学式: C₁₄H₁₉BrN₂O₂
• 分子量: 327.221
• InChiKey: XGGVEPZWSFYWBX-UHFFFAOYSA-N

物化性质

• 沸点：
  439.9±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-苯基哌啶-4-甲腈 、 2-(2-Bromo-ethyl)-5-butyl-4,6-dimethyl-5H-pyrrolo[3,4-c]pyrrole-1,3-dione 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以49%的产率得到1-[2-(2-Butyl-1,3-dimethyl-4,6-dioxopyrrolo[3,4-c]pyrrol-5-yl)ethyl]-4-phenylpiperidine-4-carbonitrile
  参考文献：
  名称：

  Synthesis and analgesic action of N-(substituted-ethyl)pyrrole-3,4-dicarboximides

  摘要：

  We prepared a series of new N-[2-(4-substitutedpiperazin-1-yl)ethyl]-1-(n-butyl or phenyl)-2,5-dimethyl-3,4-pyrroledicarboximides 3 and the related products 4 and 5, nine representatives of which were evaluated as potential analgesic agents in an animal model (mice). The new pyrroledicarboximides were not toxic (LD50 > or = 1466 mg/kg) and eight of them displayed analgesic activity approximately 1.5-5 times superior to that of ASA in the writhing test. However, the compounds were found to be unstable in methanol solution and in dilute bases (methanol/NaOMe). The S-A relationship is discussed.

  DOI：

  10.1016/j.farmac.2004.10.002
• 作为产物：
  描述：

  1,2-二溴乙烷 、 1-butyl-2,5-dimethylpyrrole-3,4-dicarboxyimide 生成 2-(2-Bromo-ethyl)-5-butyl-4,6-dimethyl-5H-pyrrolo[3,4-c]pyrrole-1,3-dione
  参考文献：
  名称：

  Synthesis and analgesic action of N-(substituted-ethyl)pyrrole-3,4-dicarboximides

  摘要：

  We prepared a series of new N-[2-(4-substitutedpiperazin-1-yl)ethyl]-1-(n-butyl or phenyl)-2,5-dimethyl-3,4-pyrroledicarboximides 3 and the related products 4 and 5, nine representatives of which were evaluated as potential analgesic agents in an animal model (mice). The new pyrroledicarboximides were not toxic (LD50 > or = 1466 mg/kg) and eight of them displayed analgesic activity approximately 1.5-5 times superior to that of ASA in the writhing test. However, the compounds were found to be unstable in methanol solution and in dilute bases (methanol/NaOMe). The S-A relationship is discussed.

  DOI：

  10.1016/j.farmac.2004.10.002

文献信息

• Malinka; Tatarczynska, Il Farmaco, 1993, vol. 48, # 7, p. 933 - 947
  作者：Malinka、Tatarczynska

  DOI：——

  日期：——
• Synthesis and pharmacological screening of some N-(4-substituted-piperazin-1-ylalkyl)-3,4-pyrroledicarboximides
  作者：Wiesław Malinka、Maria Sieklucka-Dziuba、Grażyna Rajtar、Andrzej Rubaj、Zdzisław Kleinrok

  DOI：10.1016/s0014-827x(99)00045-2

  日期：1999.6

  As an extension of our previous work we describe the synthesis and pharmacological investigation of a new series of derivatives of pyrrole-3,4-dicarboximide possessing the 4-substitutecl-piperazin-1-ylalkyl group linked to the imide nitrogen. The products were-evaluated for acute toxicity, and effectiveness in a series of CNS and arterial blood pressure tests. The preliminary pharmacological screening was determined in animal models. Several compounds demonstrated moderate to high analgesic activity in the 'writhing syndrome' test (5f-1/640 LD50). Some of the structure-activity relationships are also discussed. (C) 1999 Elsevier Science S.A. All rights reserved.
• Malinka; Sieklucka-Dziuba; Robak, Il Farmaco, 1994, vol. 49, # 7-8, p. 481 - 487
  作者：Malinka、Sieklucka-Dziuba、Robak、Kleinrok

  DOI：——

  日期：——
• Synthesis and analgesic action of N-(substituted-ethyl)pyrrole-3,4-dicarboximides
  作者：W. Malinka、M. Kaczmarz、A. Redzicka、B. Filipek、J. Sapa

  DOI：10.1016/j.farmac.2004.10.002

  日期：2005.1

  We prepared a series of new N-[2-(4-substitutedpiperazin-1-yl)ethyl]-1-(n-butyl or phenyl)-2,5-dimethyl-3,4-pyrroledicarboximides 3 and the related products 4 and 5, nine representatives of which were evaluated as potential analgesic agents in an animal model (mice). The new pyrroledicarboximides were not toxic (LD50 > or = 1466 mg/kg) and eight of them displayed analgesic activity approximately 1.5-5 times superior to that of ASA in the writhing test. However, the compounds were found to be unstable in methanol solution and in dilute bases (methanol/NaOMe). The S-A relationship is discussed.