(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-hydroxy-4-nitrophenyl)-2,4-pentadienamide | 1313740-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-hydroxy-4-nitrophenyl)-2,4-pentadienamide
• 英文别名: (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-hydroxy-4-nitrophenyl)penta-2,4-dienamide
• CAS: 1313740-72-5
• 化学式: C₁₈H₁₄N₂O₆
• 分子量: 354.319
• InChiKey: WLYGTQMYYAPSQJ-ZPUQHVIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胡椒碱 在 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 95.0h， 生成 (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-hydroxy-4-nitrophenyl)-2,4-pentadienamide
  参考文献：
  名称：

  Disruption of redox homeostasis with synchronized activation of apoptosis highlights the antifilarial efficacy of novel piperine derivatives: An in vitro mechanistic approach

  摘要：

  DOI：

  10.1016/j.freeradbiomed.2021.04.026

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.
• 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
• Disruption of redox homeostasis with synchronized activation of apoptosis highlights the antifilarial efficacy of novel piperine derivatives: An in vitro mechanistic approach
  作者：Nikhilesh Joardar、Pradip Shit、Satyajit Halder、Utsab Debnath、Sudipto Saha、Anup Kumar Misra、Kuladip Jana、Santi P. Sinha Babu

  DOI：10.1016/j.freeradbiomed.2021.04.026

  日期：2021.6