(2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid N-(n-propyl)amide | 1087058-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid N-(n-propyl)amide
• 英文别名: 5-(3,4-methylenedioxyphenyl)-2E,4E-pentadienoic acid n-propyl amide；(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N-propylpenta-2,4-dienamide；5-(3,4-methylenedioxyphenyl)-N-propyl-2E,4E-pentadienamide；(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-propylpenta-2,4-dienamide
• CAS: 1087058-15-8
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: DPXAATAFNIAPIL-GGWOSOGESA-N

物化性质

• 熔点：
  151-153 °C(Solvent: Ethyl acetate ; Ligroine)
• 沸点：
  475.3±45.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid N-(n-propyl)amide 在 palladium on activated charcoal 、 氢气 作用下， 反应 2.0h， 生成 5-(1,3-benzodioxol-5-yl)-N-propylpentanamide
  参考文献：
  名称：

  Synthesis and inhibitory effect of piperine derivates on monoamine oxidase

  摘要：

  A series of piperine derivates (1-19) have been designed, synthesized and evaluated in vitro for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. It is worth noting that most of the small amine moieties substituted on the piperidine ring proved to be potent and selective inhibitors of MAO-B rather than of MAO-A. 5-(3,4-methylenedioxyphenyl)-2E,4E-pentadienoic acid n-propyl amide (3) showed the greatest MAO-B inhibitory activity (IC50(MAO-B) = 0.045 mu M) and good selectivity (IC50(MAO-A) = 3.66 mu M). The conjugated double bond and carbonyl group of piperine are proved to be an essential feature for piperine and related alkylamides to exhibit MAO-inhibitory activity. Binding mode of the titled compounds was predicted using FlexX algorithm. The design and optimization of novel small molecule monoamine oxidase inhibitors will be guided by the results of this report. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.090
• 作为产物：
  描述：

  胡椒碱 在 草酰氯 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid N-(n-propyl)amide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Piperic Acid Amides as Free Radical Scavengers and α-Glucosidase Inhibitors

  摘要：

  合成了一系列胡椒酸酰胺（4–24, 29, 30），并评估了它们对1,1-二苯基-2-苦苷肼（DPPH）自由基的清除活性及α-葡萄糖苷酶的抑制活性。在合成的化合物中，含有邻甲氧基苯酚、儿茶酚或5-羟基吲哚基团的酰胺11、13和15表现出强效的DPPH自由基清除活性（11: EC50 140 µM; 13: EC50 28 µM; 15: EC50 20 µM）。酰胺10、18和23则展现出更高的α-葡萄糖苷酶抑制活性（10: IC50 21 µM; 18: IC50 21 µM; 23: IC50 12 µM）。这些数据显示，结合胺的疏水性是α-葡萄糖苷酶抑制活性的一个重要决定因素。此外，酰胺13和15同时表现出强效的DPPH自由基清除活性和α-葡萄糖苷酶抑制活性（13: IC50 46 µM; 15: IC50 46 µM）。这是首次报告胡椒酸酰胺的DPPH自由基清除活性和α-葡萄糖苷酶抑制活性，并暗示这些酰胺可能作为开发具有抗氧化活性的新型α-葡萄糖苷酶抑制剂的先导化合物。

  DOI：

  10.1248/cpb.c14-00874

文献信息

• [EN] ANTITUBERCULAR COMPOUNDS AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] COMPOSÉS ANTI TUBERCULOSE ET PROCÉDÉ DE LEUR PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014128724A1

  公开（公告）日：2014-08-28

  The patent discloses silicon analogs of piperine of formula I with increased antibacterial efficacy and their preparation thereof.

  该专利揭示了具有增强抗菌功效的化学式I的辣椒素硅类似物及其制备方法。
• Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors
  作者：Payare L. Sangwan、Jawahir L. Koul、Surrinder Koul、Mallepally V. Reddy、Niranjan Thota、Inshad A. Khan、Ashwani Kumar、Nitin P. Kalia、Ghulam N. Qazi

  DOI：10.1016/j.bmc.2008.09.042

  日期：2008.11

  Based on our recent findings that piperine is a potent Staphylococcus aureus NorA efflux pump inhibitor (EPI), 38 piperine analogs were synthesized and bioevaluated for their EPI activity. Twenty-five of them were found active with potentiating activity equivalent or more than known EPIs like reserpine, carsonic acid and verapamil. The inhibitory mechanism of the compounds was confirmed by efflux inhibition assay using ethidium bromide as NorA substrate. The present communication describes the synthesis, bioevaluation and structure related activity of these efflux pump inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.
• Wahab, Aneela; Sultana, Amina; Khan, Khalid Mohammed, Journal of the Chemical Society of Pakistan, 2015, vol. 37, # 5, p. 1008 - 1014
  作者：Wahab, Aneela、Sultana, Amina、Khan, Khalid Mohammed、Sherwani, Sikandar K.、Perveen, Zeba、Taha, Muhammad、Karim, Aneela

  DOI：——

  日期：——
• Verfahren zur Herstellung von Piperonylidencrotonsäureamiden
  申请人：HAARMANN & REIMER GMBH

  公开号：EP0002735B1

  公开（公告）日：1980-12-10
• US4209446A
  申请人：——

  公开号：US4209446A

  公开（公告）日：1980-06-24