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

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-(3,4-dimethoxyphenyl)ethyl)-2,4-pentadienamide
• 英文别名: (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]penta-2,4-dienamide
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: PZMGRWSIHZQBAM-GGWOSOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胡椒碱 在 氢氧化钾 、 草酰氯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-(3,4-dimethoxyphenyl)ethyl)-2,4-pentadienamide
  参考文献：
  名称：

  Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi

  摘要：

  We describe herein an evaluation of trypanocidal effects of the natural alkaloid piperine and twelve synthetic derivatives against epimastigote and amastigote forms of the protozoan parasite Trypanosoma cruzi, the causative agent of the incurable human disease, Chagas' disease. The results obtained point to piperine as a suitable template for the development of new drugs with trypanocidal activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.019

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