(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-diisopropyl-2,4-pentadienamide

• 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-(1,3-benzodioxol-5-yl)-N,N-diisopropyl-2,4-pentadienamide
• 英文别名: (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N,N-diisopropylpenta-2,4-dienamide；SCT-46；(2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid N,N-diisopropylamide；N-Piperoyl-N,N-diisopropylamine；(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-di(propan-2-yl)penta-2,4-dienamide
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: XUXUBWLCLZNEFG-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胡椒碱 在 lithium hydroxide 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 146.0h， 生成 (2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-diisopropyl-2,4-pentadienamide
  参考文献：
  名称：

  Synthesis and insecticidal activity of new amide derivatives of piperine

  摘要：

  DOI：

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

文献信息

• Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives
  作者：Angela Schöffmann、Laurin Wimmer、Daria Goldmann、Sophia Khom、Juliane Hintersteiner、Igor Baburin、Thomas Schwarz、Michael Hintersteininger、Peter Pakfeifer、Mouhssin Oufir、Matthias Hamburger、Thomas Erker、Gerhard F. Ecker、Marko D. Mihovilovic、Steffen Hering

  DOI：10.1021/jm5002277

  日期：2014.7.10

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.
• 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
• Verfahren zur Herstellung von Piperonylidencrotonsäureamiden
  申请人：HAARMANN & REIMER GMBH

  公开号：EP0002735B1

  公开（公告）日：1980-12-10
• NOVEL PIPERINE DERIVATIVES AS GABA-A RECEPTORS MODULATORS
  申请人：Universität Wien

  公开号：EP2519511B1

  公开（公告）日：2015-12-16