(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(4-methylpiperazin-1-yl)penta-2,4-dien-1-one

• 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-(benzo[d][1,3]dioxol-5-yl)-1-(4-methylpiperazin-1-yl)penta-2,4-dien-1-one
• 英文别名: SCT-81；(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(4-methylpiperazin-1-yl)penta-2,4-dien-1-one
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: BAIPTFNICURJIB-ZUVMSYQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(4-methylpiperazin-1-yl)penta-2,4-dien-1-one 在 palladium on activated charcoal 、 氢气 作用下， 反应 2.0h， 生成 5-(1,3-Benzodioxol-5-yl)-1-(4-methylpiperazin-1-yl)pentan-1-one
  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 氯化亚砜 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(4-methylpiperazin-1-yl)penta-2,4-dien-1-one
  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

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.
• Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi
  作者：Tatiana Santana Ribeiro、Leonardo Freire-de-Lima、José Osvaldo Previato、Lucia Mendonça-Previato、Norton Heise、Marco Edilson Freire de Lima

  DOI：10.1016/j.bmcl.2004.04.019

  日期：2004.7

  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.
• 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
• 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：——