diethyl (3E,5E)-4-oxo-3,5-bis(2-thienylmethylene)-1-piperidinylphosphonate | 1220189-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: diethyl (3E,5E)-4-oxo-3,5-bis(2-thienylmethylene)-1-piperidinylphosphonate
• 英文别名: (3E,5E)-1-diethoxyphosphoryl-3,5-bis(thiophen-2-ylmethylidene)piperidin-4-one
• CAS: 1220189-26-3
• 化学式: C₁₉H₂₂NO₄PS₂
• 分子量: 423.494
• InChiKey: GKRDKHSKDNDDSM-JOBJLJCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 diethyl (3E,5E)-4-oxo-3,5-bis(2-thienylmethylene)-1-piperidinylphosphonate 、 5-氯靛红 以 乙醇 为溶剂， 以80 %的产率得到diethyl (E)-[5-chloro-1′-methyl-2,4′′-dioxo-4’-(thiophen-2-yl)-5’’-(thiophen-2-ylmethylene)dispiro[indoline-3,2′-pyrrolidine-3′,3′′-piperidin]-1′′-yl]phosphonate
  参考文献：
  名称：

  Spiroindole-containing compounds bearing phosphonate group of potential Mpro-SARS-CoV-2 inhibitory properties

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115563
• 作为产物：
  描述：

  (3E,5E)-3,5-bis(2-thienylmethylene)-4-piperidone 、 氯磷酸二乙酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85 %的产率得到diethyl (3E,5E)-4-oxo-3,5-bis(2-thienylmethylene)-1-piperidinylphosphonate
  参考文献：
  名称：

  Spiroindole-containing compounds bearing phosphonate group of potential Mpro-SARS-CoV-2 inhibitory properties

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115563

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.
• Spiroindole-containing compounds bearing phosphonate group of potential Mpro-SARS-CoV-2 inhibitory properties
  作者：Mohamed S. Bekheit、Siva S. Panda、Benson M. Kariuki、Sara H. Mahmoud、Ahmed Mostafa、Adel S. Girgis

  DOI：10.1016/j.ejmech.2023.115563

  日期：2023.10