1-butyl-2,5-dimethylpyrrole-3,4-dicarboxyimide | 158576-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-butyl-2,5-dimethylpyrrole-3,4-dicarboxyimide
• 英文别名: 5-Butyl-4,6-dimethylpyrrolo[3,4-c]pyrrole-1,3-dione
• CAS: 158576-88-6
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: IEUUBRUFWZPGMZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-butyl-2,5-dimethylpyrrole-3,4-dicarboxyimide 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2-Butyl-5-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1,3-dimethylpyrrolo[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  Malinka; Sieklucka-Dziuba; Rajtar, Pharmazie, 2000, vol. 55, # 1, p. 9 - 16

  摘要：

  DOI：
• 作为产物：
  描述：

  在 磺酰氯 作用下， 以 苯 为溶剂， 反应 1.0h， 以90%的产率得到1-butyl-2,5-dimethylpyrrole-3,4-dicarboxyimide
  参考文献：
  名称：

  Malinka, W.; Bodalski, T., Polish Journal of Chemistry, 1994, vol. 68, # 2, p. 297 - 308

  摘要：

  DOI：

文献信息

• COX-1/COX-2 inhibition activities and molecular docking study of newly designed and synthesized pyrrolo[3,4-c]pyrrole Mannich bases
  作者：Aleksandra Redzicka、Łukasz Szczukowski、Andrzej Kochel、Benita Wiatrak、Katarzyna Gębczak、Żaneta Czyżnikowska

  DOI：10.1016/j.bmc.2019.07.033

  日期：2019.9

  In the present paper we describe the biological activity of newly designed and synthesized series of pyrrolo[3,4-c]pyrrole Mannich bases (7a-n). The Mannich bases were obtained in good yields by one-pot, three-component condensation of pyrrolo[3,4-c]pyrrole scaffold (6a-c) with secondary amines and an excess of formaldehyde solution in C2H5OH. The chemical structures of the compounds were characterized

  在本文中，我们描述了新设计和合成的吡咯并[3,4-c]吡咯曼尼希碱（7a-n）系列的生物活性。曼尼希碱是通过吡咯并[3,4-c]吡咯支架（6a-c）与仲胺和过量的甲醛在C2H5OH中的溶液一锅，三组分缩合获得的。化合物的化学结构通过1 H NMR，13 C NMR，FT-IR和元素分析进行​​表征。此外，已经记录了化合物7l的单晶X射线衍射。通过比色抑制剂筛选试验研究了所有合成的衍生物抑制COX-1和COX-2酶的能力。为了分析配体与环氧合酶之间的分子间相互作用，分子对接模拟的结果为实验数据提供了支持。
• Design, Synthesis, Biological Evaluation, and Molecular Docking Study of 4,6-Dimethyl-5-aryl/alkyl-2-[2-hydroxy-3-(4-substituted-1-piperazinyl)propyl]pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-diones as Anti-Inflammatory Agents with Dual Inhibition of COX and LOX
  作者：Aleksandra Redzicka、Benita Wiatrak、Izabela Jęśkowiak-Kossakowska、Andrzej Kochel、Remigiusz Płaczek、Żaneta Czyżnikowska

  DOI：10.3390/ph16060804

  日期：——

  In the present study, we characterize the biological activity of a newly designed and synthesized series of 15 compounds 2-[2-hydroxy-3-(4-substituted-1-piperazinyl)propyl] derivatives of pyrrolo[3,4-c]pyrrole 3a–3o. The compounds were obtained with good yields of pyrrolo[3,4-c]pyrrole scaffold 2a–2c with secondary amines in C2H5OH. The chemical structures of the compounds were characterized by 1H-NMR

  在本研究中，我们表征了新设计和合成的一系列 15 种吡咯并[3,4-c]化合物 2-[2-羟基-3-(4-取代-1-哌嗪基)丙基]衍生物的生物活性吡咯3a-3o。这些化合物在 C2H5OH 中与仲胺一起获得了吡咯并[3,4-c]吡咯支架 2a-2c 的高产率。通过1H-NMR、13C-NMR、FT-IR和MS对化合物的化学结构进行了表征。通过比色抑制剂筛选试验，研究了所有新化合物抑制三种酶（即 COX-1、COX-2 和 LOX）活性的效力。为了分析配体与环加氧酶/脂加氧酶之间相互作用的结构基础，实验数据得到了分子对接模拟结果的支持。
• Malinka; Tatarczynska, Il Farmaco, 1993, vol. 48, # 7, p. 933 - 947
  作者：Malinka、Tatarczynska

  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.
• 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.