(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N,N-diethylpenta-2,4-dienamide | 263744-04-3

• 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)-N,N-diethylpenta-2,4-dienamide
• 英文别名: 5-(1,3-Benzodioxol-5-yl)-N,N-diethyl-2,4-pentadienamide；(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-diethylpenta-2,4-dienamide
• CAS: 263744-04-3
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: HERKSPCMCQYVSE-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N,N-diethylpenta-2,4-dienamide 在 5% Pd/C 、 氢气 作用下， 反应 4.0h， 以98%的产率得到5-(3,4-methylenedioxyphenyl)pentanoic acid N,N-diethylamide
  参考文献：
  名称：

  Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.09.042
• 作为产物：
  描述：

  胡椒碱 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N,N-diethylpenta-2,4-dienamide
  参考文献：
  名称：

  胡椒碱及其合成酰胺类似物的结构-活性关系具有预防体外实验诱导的内质网应激的治疗潜力。

  摘要：

  内质网（ER）是参与蛋白质折叠和成熟的关键细胞器。新兴的研究表明内质网应激在慢性肾脏疾病发展中的作用。因此，迫切需要能够减轻ER应力并预防CKD的化合物。据报道，胡椒碱及其类似物表现出多种药理活性。然而，它们对肾细胞中的内质网应激的功效尚未得到研究。因此，本研究的目标是使用衣康霉素诱导的正常大鼠肾脏（NRK-52E）细胞体外模型，合成酰胺取代的胡椒碱类似物，并筛选其药理活性以缓解ER应激。合成了五个酰胺取代的胡椒碱类似物，并通过相关的光谱技术阐明了它们的化学结构。使用衣霉素开发了ER应激的体外模型，并筛选了感兴趣的化合物对细胞生存力的影响，以及ER伴侣GRP78，促凋亡ER应激标记CHOP以及凋亡的半胱氨酸蛋白酶3和12的表达（通过蛋白质印迹）。我们的发现表明，暴露于衣霉素（0.5μg/ mL）2 h会诱导GRP78和CHOP的表达以及凋亡标记（caspase-3和caspase-12）的

  DOI：

  10.1007/s12192-017-0786-9

文献信息

• 一种胡椒碱衍生物及其制备方法和用途
  申请人：四川大学

  公开号：CN111072597B

  公开（公告）日：2022-12-09

  本发明提供了一种胡椒碱衍生物及其制备方法和用途。该胡椒碱衍生物为式(I)所示的化合物、或其盐、或其立体异构体、或其水合物。本发明化合物能够有效保护神经细胞，提高神经细胞的存活率，因此，本发明化合物可以有效治疗神经退行性疾病，可以用于制备治疗神经退行性疾病的药物。
• [EN] NOVEL PIPERINE DERIVATIVES AS GABA - A RECEPTORS MODULATORS<br/>[FR] NOUVEAUX DÉRIVÉS PIPÉRINES COMME MODULATEURS DES RÉCEPTEURS GABA - A
  申请人：UNIV WIEN

  公开号：WO2011080313A1

  公开（公告）日：2011-07-07

  The present invention encompasses novel piperin compounds of general formula (I) wherein R1, R2, R3, m and n are defined as in claim 1, which are suitable for the prevention and/or treatment of diseases mediated by modulation of GABAA receptor and the use thereof for preparing a medicament having the above mentioned properties.

  本发明涵盖了一种新型的辣椒素化合物，其一般化学式为（I），其中R1、R2、R3、m和n的定义如索赔1所述，适用于通过调节GABAA受体来预防和/或治疗由此介导的疾病，并用于制备具有上述特性的药物。
• 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.
• Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson’s disease via the activation of Nrf2/keap1 pathway
  作者：Lun Wang、Xiaoying Cai、Mingsong Shi、Linlin Xue、Shuang Kuang、Ruiling Xu、Wenyan Qi、Yan Li、Xu Ma、Ruijia Zhang、Feng Hong、Haoyu Ye、Lijuan Chen

  DOI：10.1016/j.ejmech.2020.112385

  日期：2020.8

  Parkinson's disease (PD) is a slowly progressive and complex neurodegenerative disorder. Up to date, there are no approved drugs that could slow or reverse the neurodegenerative process of PD. Here, we reported the synthesis of series of piperine analogues and the evaluation of their neuroprotective effects against hydrogen peroxide (H2O2) induced damage in the neuron-like PC12 cells. Among these analogues, 3b exhibited the most potent protection effect and its underlying mechanism was further investigated. Further results indicated that the ROS scavenging and cytoprotection effect of 3b might be related to the Nrf2 activation and upregulation of related phase II antioxidant enzymes, such as HO-1 and NQO1. In in vivo study, oral administration (100 mg/kg) of 3b significantly attenuated PD-associated behavioral deficits in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model of PD and protected tyrosine hydroxylase-immunopositive dopaminergic neurons. Our results provided evidence that 3b might be a promising candidate for Parkinson's disease treatment. (C) 2020 Elsevier Masson SAS. 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