ethyl 3-(2-chlorophenyl)-4-nitrobutanoate | 29655-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-(2-chlorophenyl)-4-nitrobutanoate
• CAS: 29655-71-8
• 化学式: C₁₂H₁₄ClNO₄
• 分子量: 271.7
• InChiKey: WIQMYZCPRVTACX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-氨甲基吡啶 、 ethyl 3-(2-chlorophenyl)-4-nitrobutanoate 、 对羟基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以44.8%的产率得到(±)-4-(2-chlorophenyl)-6-(4-hydroxyphenyl)-5-nitro-1-(pyridin-3-ylmethyl)piperidin-2-one
  参考文献：
  名称：

  Design, synthesis, and evaluation of 2-piperidone derivatives for the inhibition of β-amyloid aggregation and inflammation mediated neurotoxicity

  摘要：

  A series of novel multipotent 2-piperidone derivatives were designed, synthesized and biologically evaluated as chemical agents for the treatment of Alzheimer's disease (AD). The results showed that most of the target compounds displayed significant potency to inhibit A beta(1-42) self-aggregation. Among them, compound 7q exhibited the best inhibition of A beta(1-42) self-aggregation (59.11% at 20 mu M) in a concentration-dependent manner. Additionally, the compounds 6b, 7p and 7q as representatives were found to present anti-inflammation properties in lipopolysaccharide (LPS)-induced microglial BV-2 cells. They could effectively suppress the production of pro-inflammatory cytokines such as TNF-alpha, IL-1 beta and IL-6. Meanwhile, compound 7q could prevent the neuronal cell SH-SY5Y death by LPS-stimulated microglia cell activation mediated neurotoxicity. The molecular modeling studies demonstrated that compounds matched the pharmacophore well and had good predicted physicochemical properties and estimated IC50 values. Moreover, compound 7q exerted a good binding to the active site of myeloid differentiation factor 88 (MyD88) through the docking analysis and could interfere with its homodimerization or heterodimerization. Consequently, these compounds emerged as promising candidates for further development of novel multifunctional agents for AD treatment. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.010
• 作为产物：
  描述：

  2-氯苯甲醛 在 哌啶 、 吡啶 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 32.0h， 生成 ethyl 3-(2-chlorophenyl)-4-nitrobutanoate
  参考文献：
  名称：

  Design, synthesis, and evaluation of 2-piperidone derivatives for the inhibition of β-amyloid aggregation and inflammation mediated neurotoxicity

  摘要：

  A series of novel multipotent 2-piperidone derivatives were designed, synthesized and biologically evaluated as chemical agents for the treatment of Alzheimer's disease (AD). The results showed that most of the target compounds displayed significant potency to inhibit A beta(1-42) self-aggregation. Among them, compound 7q exhibited the best inhibition of A beta(1-42) self-aggregation (59.11% at 20 mu M) in a concentration-dependent manner. Additionally, the compounds 6b, 7p and 7q as representatives were found to present anti-inflammation properties in lipopolysaccharide (LPS)-induced microglial BV-2 cells. They could effectively suppress the production of pro-inflammatory cytokines such as TNF-alpha, IL-1 beta and IL-6. Meanwhile, compound 7q could prevent the neuronal cell SH-SY5Y death by LPS-stimulated microglia cell activation mediated neurotoxicity. The molecular modeling studies demonstrated that compounds matched the pharmacophore well and had good predicted physicochemical properties and estimated IC50 values. Moreover, compound 7q exerted a good binding to the active site of myeloid differentiation factor 88 (MyD88) through the docking analysis and could interfere with its homodimerization or heterodimerization. Consequently, these compounds emerged as promising candidates for further development of novel multifunctional agents for AD treatment. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.010

文献信息

• Potent and selective α1A adrenoceptor partial agonists—Novel imidazole frameworks
  作者：Gavin A. Whitlock、Paul E. Brennan、Lee R. Roberts、Alan Stobie

  DOI：10.1016/j.bmcl.2009.03.162

  日期：2009.6

  Novel imidazole frameworks have been identified as potent partial agonists of the alpha(1A) adrenergic receptor, with good selectivity over the alpha(1B), alpha(1D) and alpha(2A) receptor sub-types. Nitrile 28 possessed attractive CNS drug-like properties with good membrane permeability and no P-pg mediated efflux. 28 also possessed excellent solubility, metabolic stability and wide ligand selectivity. (C) 2009 Elsevier Ltd. All rights reserved.