(E)-3-(4-(吡咯烷-1-基)苯基)丙烯酸 | 199679-02-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: (E)-3-(4-(吡咯烷-1-基)苯基)丙烯酸
• 英文名称: (E)-3-(4-(pyrrolidin-1-yl)phenyl)acrylic acid
• 英文别名: (E)-3-(4-pyrrolidin-1-ylphenyl)prop-2-enoic acid
• CAS: 199679-02-2
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: JPWVQUNJAKZADY-VMPITWQZSA-N

物化性质

• 沸点：
  416.7±28.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  哌啶 、 (E)-3-(4-(吡咯烷-1-基)苯基)丙烯酸 在 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以75.3%的产率得到(E)-1-(piperidin-1-yl)-3-(4-(pyrrolidin-1-yl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson’s disease via the activation of Nrf2/keap1 pathway

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2020.112385
• 作为产物：
  描述：

  4-(1-吡咯啉基)苯甲醛 在 水 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成 (E)-3-(4-(吡咯烷-1-基)苯基)丙烯酸
  参考文献：
  名称：

  作为黑色素浓缩激素受体 1 (MCHR1) 拮抗剂的喹唑啉衍生物的设计和优化：第 2 部分

  摘要：

  黑色素浓缩激素受体 1 (MCHR1) 拮抗剂具有治疗肥胖和多种中枢神经系统疾病的潜力。在上一篇文章中，我们描述了一系列新型喹唑啉作为 MCHR1 拮抗剂，并通过早期先导证明了体内原理证明。在此，我们描述了详细的 SAR 和 SPR 研究，以确定在亚慢性 DIO 模型中具有良好疗效且具有良好心血管安全窗口的优化先导候选药物。

  DOI：

  10.1016/j.bmcl.2012.03.049

文献信息

• Design, synthesis, 3D pharmacophore, QSAR, and docking studies of carboxylic acid derivatives as Histone Deacetylase inhibitors and cytotoxic agents
  作者：Mona M. Abdel-Atty、Nahla A. Farag、Shaymaa E. Kassab、Rabah A.T. Serya、Khaled A.M. Abouzid

  DOI：10.1016/j.bioorg.2014.08.006

  日期：2014.12

  In this study, five series of (E)-6-(4-substituted phenyl)-4-oxohex-5-enoic acids IIb-f (E), (E)-3-(4-(substituted)-phenyl) acrylic acids IIIa-g (E), 4-(4-(substituted) phenylamino)-4-oxobutanoic acids VIa,b,e, 5-(4-(substituted) phenylamino)-5-oxopentanoic acids VIIa,f and 2-[(4-(substituted) phenyl) carbamoyl] benzoic acids VIIIa,e were designed and synthesized. Selected compounds were screened in vitro for their cytotoxic effect on 60 human NCI tumor cell lines. Compound IIf (E) displayed significant inhibitory activity against NCI Non-Small Cell Lung A549/ATCC Cancer cell line (68% inhibition) and NCI-H460 Cancer cell line (66% inhibition). Moreover, the final compounds were evaluated in vitro for their cytotoxic activity on HepG2 Cancer cell line in which histone deacetylase (HDAC) is overexpressed. Compounds IIc (E), IIf (E), IIIb (E), and IIIg (E) exhibited the highest cytotoxic activity against HepG2 human cancer cell lines with IC50 ranging from 2.27 to 10.71 mu M. In addition, selected compounds were tested on histone deacetylase isoforms (HDAC1-11). Molecular docking simulation was also carried out for HDLP enzyme to investigate their HDAC binding affinity. In addition, generation of 3D-pharmacophore model and quantitative structure activity relationship (QSAR) models were combined to explore the structural requirements controlling the observed cytotoxic properties. (C) 2014 Elsevier Inc. All rights reserved.
• CARBOLINE DERIVATIVES
  申请人：ICOS CORPORATION

  公开号：EP0912567A1

  公开（公告）日：1999-05-06
• TETRAHYDROISOQUINOLINE DERIVATIVES AND THEIR PHARMACEUTICAL USE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0922035B1

  公开（公告）日：2001-02-07
• US6043252A
  申请人：——

  公开号：US6043252A

  公开（公告）日：2000-03-28
• US6117881A
  申请人：——

  公开号：US6117881A

  公开（公告）日：2000-09-12