ethyl 2-cyano-3-(6-nitrobenzo-1,3-dioxol-5-yl)acrylate | 33657-15-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 2-cyano-3-(6-nitrobenzo-1,3-dioxol-5-yl)acrylate
• 英文别名: 2-cyano-3-(6-nitro-benzo[1,3]dioxol-5-yl)-acrylic acid ethyl ester；Ethyl 2-cyano-3-(6-nitro-1,3-benzodioxol-5-yl)prop-2-enoate
• CAS: 33657-15-7
• 化学式: C₁₃H₁₀N₂O₆
• mdl: MFCD00414388
• 分子量: 290.232
• InChiKey: BDZOKVLURQFWED-UHFFFAOYSA-N

物化性质

• 沸点：
  474.3±45.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-3-(6-nitrobenzo-1,3-dioxol-5-yl)acrylate 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 49.5h， 生成 LASSBio-947
  参考文献：
  名称：

  Docking, synthesis and pharmacological activity of novel urea-derivatives designed as p38 MAPK inhibitors

  摘要：

  p38 mitogen-activated protein kinase (p38 MAPK) is an important signal transducing enzyme involved in many cellular regulations, including signaling pathways, pain and inflammation. Several p38 MAPK inhibitors have been developed as drug candidates to treatment of autoimmune disorders, such as rheumatoid arthritis. In this paper we reported the docking, synthesis and pharmacological activity of novel urea-derivatives (4a-e) designed as p38 MAPK inhibitors. These derivatives presented good theoretical affinity to the target p38 MAPK, standing out compound 4e (LASSBio-998), which showed a better score value compared to the prototype GK-00687. This compound was able to reduce in vitro TNF-alpha production and was orally active in a hypernociceptive murine model sensible to p38 MAPK inhibitors. Otherwise, compound 4e presented a dose-dependent analgesic effect in a model of antigen (mBSA)-induced arthritis and anti-inflammatory profile in carrageenan induced paw edema, indicating its potential as a new antiarthritis prototype. (c) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.006
• 作为产物：
  描述：

  胡椒醛 在 aluminum oxide 、 potassium fluoride 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 ethyl 2-cyano-3-(6-nitrobenzo-1,3-dioxol-5-yl)acrylate
  参考文献：
  名称：

  Docking, synthesis and pharmacological activity of novel urea-derivatives designed as p38 MAPK inhibitors

  摘要：

  p38 mitogen-activated protein kinase (p38 MAPK) is an important signal transducing enzyme involved in many cellular regulations, including signaling pathways, pain and inflammation. Several p38 MAPK inhibitors have been developed as drug candidates to treatment of autoimmune disorders, such as rheumatoid arthritis. In this paper we reported the docking, synthesis and pharmacological activity of novel urea-derivatives (4a-e) designed as p38 MAPK inhibitors. These derivatives presented good theoretical affinity to the target p38 MAPK, standing out compound 4e (LASSBio-998), which showed a better score value compared to the prototype GK-00687. This compound was able to reduce in vitro TNF-alpha production and was orally active in a hypernociceptive murine model sensible to p38 MAPK inhibitors. Otherwise, compound 4e presented a dose-dependent analgesic effect in a model of antigen (mBSA)-induced arthritis and anti-inflammatory profile in carrageenan induced paw edema, indicating its potential as a new antiarthritis prototype. (c) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.006

文献信息

• Low-Valent Titanium Induced Reductive Coupling of Nitriles with Nitro Compounds
  作者：Longhu Zhou、Yongmin Zhang

  DOI：10.1080/00397919808004430

  日期：1998.9

  Abstract The intermolecular and intramolecular reductive coupling of a cyano group with a nitro group induced by a low-valent titanium reagent prepared from TiCl4/Sm was studied. Amidines and 2-aminoquinolines derivatives are preparied in good yields under mild conditions respectively.

  摘要 研究了由TiCl4/Sm 制备的低价钛试剂诱导氰基与硝基的分子间和分子内还原偶联。脒和 2-氨基喹啉衍生物分别在温和条件下以良好的收率制备。
• Facile and Efficient Synthesis of 2-Aminoquinoline-3-carboxylic Acid Derivatives via Reductive Cyclization of Nitro and Cyano Groups Induced by Low-valent Titanium
  作者：Longhu Zhou、Sujiang Tu、Daqin Shi、Guiyuan Dai

  DOI：10.1039/a800588e

  日期：——

  A short and facile synthesis of a series of 2-aminoquinoline-3-carboxylic acid derivatives was accomplished in good yields via the intramolecular reductive cyclization of nitrocyano olefins promoted by TiCl4/Zn.

  通过四氯化钛/锌促进的硝基氰基烯烃的分子内还原环化反应，成功实现了一系列2-氨基喹啉-3-羧酸衍生物的简便且高效的合成，产率良好。
• Expedious and practical synthesis of the bioactive alkaloids rutaecarpine, euxylophoricine A, deoxyvasicinone and their heterocyclic homologues
  作者：Abdulkareem Hamid、Abdelhakim Elomri、Adam Daïch

  DOI：10.1016/j.tetlet.2006.01.031

  日期：2006.3

  deoxyvasicinone (3), is reported from suitable aromatic amino acids 7 or corresponding aromatic amino esters 8 and imino-thioethers 5 or 6 in a one-step sequence in moderate to good yields. The key step of this methodology is based on an intramolecular aza-displacement of a methylthio group followed by spontaneous cyclodehydration. Furthermore, when aromatic amino esters 8 were used instead of amino acids

  从适当的芳香族氨基酸7或相应的芳香族氨基酯8或相应的芳香族氨基酯8和亚氨基硫醚5或6中报告了嘧啶β-咔啉1和2的有效组装，包括生物活性生物碱芸香菜碱，硫氧鸟嘌呤A和脱氧vasicinone（3）。一步顺序以中等到良好的产量。该方法的关键步骤基于甲硫基的分子内氮杂置换，然后进行自发的环脱水。此外，当使用芳族氨基酯8代替氨基酸时，发生串联氨基-甲硫基置换/氨基酯环化。
• Low-Valent Titanium Induced Novel Reductive Cyclization of α,β-Unsaturated Nitrile Compounds
  作者：Long-hu Zhou、Shu-jiang Tu、Da-qin Shi、Gui-yuan Dai、Wei-xing Chen

  DOI：10.1055/s-1998-2082

  日期：1998.6
• Kametani,T. et al., Chemical and pharmaceutical bulletin, 1971, vol. 19, p. 1321 - 1324
  作者：Kametani,T. et al.

  DOI：——

  日期：——