(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N-ethylpenta-2,4-dienamide

• 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-ethylpenta-2,4-dienamide
• 英文别名: (2E,4E)-5-(benzo[d][1,3]dioxazol-5-yl)-N-ethylpenta-2,4-dienamide；(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-ethylpenta-2,4-dienamide
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: AANYEPAUNZGSGK-GGWOSOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胡椒碱 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N-ethylpenta-2,4-dienamide
  参考文献：
  名称：

  Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation

  摘要：

  A wide range of piperine analogues has been synthesised in order to undertake a structure-activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2E,4E-dienoic acid methyl ester (3a), 1-E,E-piperinoyl-isobutylamine (4f) and 1-(3,4-methylenedioxyphenyl)-pentanoic acid cyclohexyl amide (20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.036

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。
• 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
• US4209446A
  申请人：——

  公开号：US4209446A

  公开（公告）日：1980-06-24
• US4209445A
  申请人：——

  公开号：US4209445A

  公开（公告）日：1980-06-24