(E)-3-(4-(piperidin-1-yl)phenyl)acrylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-3-(4-(piperidin-1-yl)phenyl)acrylic acid
• 英文别名: (2E)-3-(4-piperidin-1-ylphenyl)acrylic acid；(E)-3-(4-piperidin-1-ylphenyl)prop-2-enoic acid
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: YTISCXXFAWKVSE-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4-(2,4,6-三甲基苯基)-2-氨基噻唑 、 (E)-3-(4-(piperidin-1-yl)phenyl)acrylic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 反应 0.5h， 以33%的产率得到(E)-N-(4-mesitylthiazol-2-yl)-3-(4-(piperidin-1-yl)phenyl)acrylamide
  参考文献：
  名称：

  Synthesis and biological evaluation of N-(4-phenylthiazol-2-yl)cinnamamide derivatives as novel potential anti-tumor agents

  摘要：

  在这项研究中，合成了一系列新型的N-(4-苯基噻唑-2-基)-肉桂酰胺衍生物（7a–8n），并评估了它们在体外对细胞增殖的抑制活性。

  DOI：

  10.1039/c4md00573b
• 作为产物：
  描述：

  对氟苯甲醛 在 哌啶 、 吡啶 、 Aliquat (at)366 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (E)-3-(4-(piperidin-1-yl)phenyl)acrylic acid
  参考文献：
  名称：

  Design, synthesis, 3D pharmacophore, QSAR, and docking studies of carboxylic acid derivatives as Histone Deacetylase inhibitors and cytotoxic agents

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2014.08.006

文献信息

• Synthesis and biological evaluation of N-(4-phenylthiazol-2-yl)cinnamamide derivatives as novel potential anti-tumor agents
  作者：Yong Luo、Yongxia Zhu、Kai Ran、Zhihao Liu、Ningyu Wang、Qiang Feng、Jun Zeng、Lidan Zhang、Bing He、Tinghong Ye、Shirui Zhu、Xiaolong Qiu、Luoting Yu

  DOI：10.1039/c4md00573b

  日期：——

  In this study, a series of novel N-(4-phenylthiazol-2-yl)-cinnamamide derivatives (7a–8n) were synthesized and evaluated for their anti-proliferative activities in vitro.

  在这项研究中，合成了一系列新型的N-(4-苯基噻唑-2-基)-肉桂酰胺衍生物（7a–8n），并评估了它们在体外对细胞增殖的抑制活性。
• 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.