(3Z,5E)-1-methyl-3,5-bis(thiophen-2-ylmethylene)piperidin-4-one | 1220189-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3Z,5E)-1-methyl-3,5-bis(thiophen-2-ylmethylene)piperidin-4-one
• 英文别名: (3Z,5E)-1-methyl-3,5-bis(2-thienylmethylene)-4-piperidone；(3Z,5E)-1-Methyl-3,5-bis[(thiophen-2-YL)methylidene]piperidin-4-one；(3Z,5E)-1-methyl-3,5-bis(thiophen-2-ylmethylidene)piperidin-4-one
• CAS: 1220189-32-1
• 化学式: C₁₆H₁₅NOS₂
• 分子量: 301.433
• InChiKey: PLOKQQNJVRLWES-QRBCZBMESA-N

物化性质

• 沸点：
  500.7±50.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3Z,5E)-1-methyl-3,5-bis(thiophen-2-ylmethylene)piperidin-4-one 、 苯肼 以 异丙醇 为溶剂， 以96%的产率得到(E)-5-methyl-2-phenyl-3-(thiophen-2-yl)-7-(thiophen-2-ylmethylene)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]pyridine
  参考文献：
  名称：

  通过促炎和抗炎细胞因子和COX-2抑制评估，吡唑并吡啶类似物作为炎症药物的合成和发现。

  摘要：

  本文简要介绍了为合成，表征和开发（E）-5-甲基-2-苯基-3-（噻吩-2-基）-7-（噻吩-2-基亚甲基）-3,3a，4所做的努力，5,6,7-六氢-2H-吡唑并[4,3-c]吡啶及其类似物。在两步反应中，第一步是通过搅拌反应合成（3Z，5E）-1-甲基-3,5-双（噻吩-2-基亚甲基）哌啶-4-酮衍生物（3a-1）甲醇存在下1-甲基哌啶-4-酮和取代噻吩-甲醛的混合物。在第二个也是最后一个步骤中，化合物3a-1与苯基肼一起回流，以实现目标化合物（E）-5-甲基-2-苯基-3-（噻吩-2-基）-7-（噻吩-2 （-亚甲基）-3,3a，4,5,6,7-六氢-2H-吡唑并[4,3-c]吡啶及其类似物（5a-1），收率很高。通过分别执行定量促炎和抗炎蛋白（例如TNF-α，IL-1β，IL6和IL-10），这些化合物可用于评估巨噬细胞中的炎症调节特性。电子和体外COX-2抑制研究有助于了解化合物

  DOI：

  10.1016/j.bioorg.2019.103484
• 作为产物：
  描述：

  1-methyl-3,5-bis[(E)-(2-thienyl)methylidene]-4-piperidone 以 氯仿 为溶剂， 反应 6.0h， 以10%的产率得到(3Z,5E)-1-methyl-3,5-bis(thiophen-2-ylmethylene)piperidin-4-one
  参考文献：
  名称：

  Synthesis, characterization and structure–activity relationship of novel N-phosphorylated E,E-3,5-bis(thienylidene)piperid-4-ones

  摘要：

  In order to design the agents with improved antitumor activity of 3,5-bis(thienylidene)piperid-4-one type, E,E-N-phosphoryl-3,5-bis(thienylidene)piperid-4-ones 6a-c and E,E-N-omega-phosphorylalkyl-3,5-bis-(thienylidene)piperid-4-ones 7a-c were obtained via the direct phosphorylation of the parent NH-3,5-bis(thienylidene)piperid-4-one and by condensation of preformed N-phosphorylalkyl substituted piperidones with thiophene 2-carbaldehyde, respectively. The structures of the compounds were elucidated by H-1, P-31 C-13 NMR along with a single crystal X-ray diffraction analysis. Under the action of visible light thermodynamically more stable E,E-isomers slowly undergo photochemical conversion in CDCl3 solution to the corresponding E,Z-isomers and E,Z-N-methyl-3,5-bis(thienylidene)piperid-4-one 5 was isolated in individual state. The importance of phosphorylation for cytotoxic properties of 3,5bis(thienylidene)piperid-4-ones towards human carcinoma cell lines Caov3, Scov3, and A549 and influence of olefin configuration on antitumor activity were demonstrated. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.041

文献信息

• Synthesis, characterization and structure–activity relationship of novel N-phosphorylated E,E-3,5-bis(thienylidene)piperid-4-ones
  作者：Michael V. Makarov、Evgeniya S. Leonova、Ekaterina Yu. Rybalkina、Paul Tongwa、Victor N. Khrustalev、Tatiana V. Timofeeva、Irina L. Odinets

  DOI：10.1016/j.ejmech.2009.11.041

  日期：2010.3

  In order to design the agents with improved antitumor activity of 3,5-bis(thienylidene)piperid-4-one type, E,E-N-phosphoryl-3,5-bis(thienylidene)piperid-4-ones 6a-c and E,E-N-omega-phosphorylalkyl-3,5-bis-(thienylidene)piperid-4-ones 7a-c were obtained via the direct phosphorylation of the parent NH-3,5-bis(thienylidene)piperid-4-one and by condensation of preformed N-phosphorylalkyl substituted piperidones with thiophene 2-carbaldehyde, respectively. The structures of the compounds were elucidated by H-1, P-31 C-13 NMR along with a single crystal X-ray diffraction analysis. Under the action of visible light thermodynamically more stable E,E-isomers slowly undergo photochemical conversion in CDCl3 solution to the corresponding E,Z-isomers and E,Z-N-methyl-3,5-bis(thienylidene)piperid-4-one 5 was isolated in individual state. The importance of phosphorylation for cytotoxic properties of 3,5bis(thienylidene)piperid-4-ones towards human carcinoma cell lines Caov3, Scov3, and A549 and influence of olefin configuration on antitumor activity were demonstrated. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis and discovery of pyrazolo-pyridine analogs as inflammation medications through pro- and anti-inflammatory cytokine and COX-2 inhibition assessments
  作者：J. Dennis Bilavendran、A. Manikandan、P. Thangarasu、K. Sivakumar

  DOI：10.1016/j.bioorg.2019.103484

  日期：2020.1

  of methanol. In the second and final step, compounds 3a-l were refluxed with phenyl-hydrazine to achieve the target compounds (E)-5-methyl-2-phenyl-3-(thiophen-2-yl)-7-(thiophen-2-ylmethylene)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]pyridine and their analogs (5a-l) in good yield. These compounds were used to assess their inflammation regulation properties in macrophages by executing quantitative pro-inflammatory

  本文简要介绍了为合成，表征和开发（E）-5-甲基-2-苯基-3-（噻吩-2-基）-7-（噻吩-2-基亚甲基）-3,3a，4所做的努力，5,6,7-六氢-2H-吡唑并[4,3-c]吡啶及其类似物。在两步反应中，第一步是通过搅拌反应合成（3Z，5E）-1-甲基-3,5-双（噻吩-2-基亚甲基）哌啶-4-酮衍生物（3a-1）甲醇存在下1-甲基哌啶-4-酮和取代噻吩-甲醛的混合物。在第二个也是最后一个步骤中，化合物3a-1与苯基肼一起回流，以实现目标化合物（E）-5-甲基-2-苯基-3-（噻吩-2-基）-7-（噻吩-2 （-亚甲基）-3,3a，4,5,6,7-六氢-2H-吡唑并[4,3-c]吡啶及其类似物（5a-1），收率很高。通过分别执行定量促炎和抗炎蛋白（例如TNF-α，IL-1β，IL6和IL-10），这些化合物可用于评估巨噬细胞中的炎症调节特性。电子和体外COX-2抑制研究有助于了解化合物