Ethyl 2-[1-[(4-nitrophenyl)methyl]piperidin-4-yl]acetate | 185434-58-6

• 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: Ethyl 2-[1-[(4-nitrophenyl)methyl]piperidin-4-yl]acetate
• CAS: 185434-58-6
• 化学式: C₁₆H₂₂N₂O₄
• 分子量: 306.362
• InChiKey: MBUTZCIHRYVNJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[1-[(4-nitrophenyl)methyl]piperidin-4-yl]acetate 在 重铬酸吡啶 、 ammonium formate 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 4-Methyl-N-{2-methyl-1-[1-(4-nitro-benzyl)-piperidin-4-ylmethyl]-propyl}-benzamide
  参考文献：
  名称：

  Design and synthesis of novel CCR3 antagonists

  摘要：

  As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 muM in the binding assay and 0.0024 muM in the chemotaxis assay. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0960-894x(03)00748-0
• 作为产物：
  描述：

  4-哌啶酮 在 platinum(IV) oxide 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Ethyl 2-[1-[(4-nitrophenyl)methyl]piperidin-4-yl]acetate
  参考文献：
  名称：

  Design and synthesis of novel CCR3 antagonists

  摘要：

  As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 muM in the binding assay and 0.0024 muM in the chemotaxis assay. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0960-894x(03)00748-0

文献信息

• Highly Selective, Novel Analogs of 4-[2-(Diphenylmethoxy)ethyl]- 1-benzylpiperidine for the Dopamine Transporter:  Effect of Different Aromatic Substitutions on Their Affinity and Selectivity
  作者：Aloke K. Dutta、Lori L. Coffey、Maarten E. A. Reith

  DOI：10.1021/jm960638e

  日期：1997.1.1

  Several analogs of the potent and selective dopamine transporter (DAT) ligand 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine, 1a, were prepared and biologically evaluated at the dopamine and serotonin transporter (SERT) sites. Several substituents were introduced in the aromatic rings to evaluate the influences of electronic and steric interactions in their binding to the DAT. All the novel analogs showed

  制备了有效的和选择性的多巴胺转运蛋白（DAT）配体4- [2-（二苯甲氧基）乙基] -1-苄基哌啶1a的几种类似物，并在多巴胺和5-羟色胺转运蛋白（SERT）部位进行了生物学评估。在芳香环中引入了几个取代基，以评估电子和空间相互作用对DAT结合的影响。与SERT相比，所有新的类似物在DAT均表现出优先相互作用。分子的N-苄基部分的苯环中的不同芳族取代在选择性中起关键作用。通常，具有强吸电子取代基的化合物在DAT处最具活性和选择性。因此，化合物5a（R = F）和11b（R = NO2）是最有效的化合物（IC50 = 17.2和16.4 nM，选择性最高）（分别为SERT / DAT = 112和108），并且选择性远远高于GBR 12909（SERT / DAT = 6）。用噻吩环对二苯基甲氧基部分的一个苯环进行生物等位置换是可以很好地耐受的，并产生了该系列中最有效的化合物13b（IC50
• Design and synthesis of novel CCR3 antagonists
  作者：Leyi Gong、J.Heather Hogg、James Collier、Robert S. Wilhelm、Carol Soderberg

  DOI：10.1016/s0960-894x(03)00748-0

  日期：2003.10

  As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 muM in the binding assay and 0.0024 muM in the chemotaxis assay. (C) 2003 Published by Elsevier Ltd.