(2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid N-isopropylamide

• 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-isopropylamide
• 英文别名: (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-propan-2-ylpenta-2,4-dienamide
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: GHEXBVZHOBIWNE-GGWOSOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 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

• 作为产物：
  描述：

  胡椒碱 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid N-isopropylamide
  参考文献：
  名称：

  Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation

  摘要：

  A wide range of piperine analogues has been synthesised in order to undertake a structure-activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2E,4E-dienoic acid methyl ester (3a), 1-E,E-piperinoyl-isobutylamine (4f) and 1-(3,4-methylenedioxyphenyl)-pentanoic acid cyclohexyl amide (20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.036

文献信息

• 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.
• Synthesis and insecticidal activity of new amide derivatives of piperine
  作者：Vanderlúcia F de Paula、Luiz C de A Barbosa、Antônio J Demuner、Dorila Piló-Veloso、Marcelo C Picanço

  DOI：10.1002/(sici)1526-4998(200002)56:2<168::aid-ps110>3.0.co;2-h

  日期：2000.2
• US7361685B2
  申请人：——

  公开号：US7361685B2

  公开（公告）日：2008-04-22
• Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation
  作者：Radhakrishnan Venkatasamy、Laura Faas、Antony R Young、Amala Raman、Robert C Hider

  DOI：10.1016/j.bmc.2004.01.036

  日期：2004.4

  A wide range of piperine analogues has been synthesised in order to undertake a structure-activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2E,4E-dienoic acid methyl ester (3a), 1-E,E-piperinoyl-isobutylamine (4f) and 1-(3,4-methylenedioxyphenyl)-pentanoic acid cyclohexyl amide (20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.