1-(3-Phenylpropyl)-isonipecotinsaeure-ethylester | 21327-50-4

• 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: 1-(3-Phenylpropyl)-isonipecotinsaeure-ethylester
• 英文别名: Ethyl 1-(3-phenylpropyl)piperidine-4-carboxylate
• CAS: 21327-50-4
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: SSDDQYAUQSKHRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-Phenylpropyl)-isonipecotinsaeure-ethylester 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 4-[Bis-(4-fluoro-phenyl)-methoxymethyl]-1-(3-phenyl-propyl)-piperidine
  参考文献：
  名称：

  新型4- [2- [2- [双（4-氟苯基）甲氧基]乙基] -1-（3-苯基丙基）哌啶类似物的结构活性关系研究：在多巴胺和5-羟色胺转运蛋白位点的合成和生物学评估。

  摘要：

  制备了强效多巴胺（DA）转运蛋白配体4- [2- [双（4-氟苯基）-甲氧基]乙基] -1-（3-苯基丙基）哌啶的类似物1b，并对其在生物学上的结合进行了生物学评估。大鼠纹状体膜中的DA和血清素（5HT）转运蛋白。在这些分子中引入了不同的烷基链长度和取代基，以产生针对DA转运蛋白的最佳活性和选择性。通常，未取代的和氟取代的化合物对于DA转运蛋白是最活跃和最具选择性的。化合物4- [2-（二苯基甲氧基）乙基] -1-苄基哌啶9a显示出高效价，并且在该系列化合物中对DA转运蛋白的选择性最高（5HT / DA = 49）。发现其中一些新颖的类似物比原始GBR 12909分子在DA转运蛋白上的结合更具选择性，

  DOI：

  10.1021/jm9506581
• 作为产物：
  描述：

  哌啶-4-甲酸乙酯 、 1-氯-3-苯基丙烷 在 三乙胺 作用下， 以 甲苯 为溶剂， 以65%的产率得到1-(3-Phenylpropyl)-isonipecotinsaeure-ethylester
  参考文献：
  名称：

  Cignarella; Villa; Barlocco, Il Farmaco, 1993, vol. 48, # 10, p. 1439 - 1445

  摘要：

  DOI：

文献信息

• Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs
  作者：Paul J. Gilligan、Gary A. Cain、Thomas E. Christos、Leonard Cook、Spencer Drummond、Alexander L. Johnson、Ahmed A. Kergaye、John F. McElroy、Kenneth W. Rohrbach

  DOI：10.1021/jm00101a012

  日期：1992.11

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.
• Identification of novel scaffolds for potential anti- Helicobacter pylori agents based on the crystal structure of H. pylori 3-deoxy- d -manno-octulosonate 8-phosphate synthase ( Hp KDO8PS)
  作者：Sujin Cho、Hookang Im、Ki-Young Lee、Jie Chen、Hae Ju Kang、Hye-Jin Yoon、Kyung Hoon Min、Kang Ro Lee、Hyun-Ju Park、Bong-Jin Lee

  DOI：10.1016/j.ejmech.2015.11.036

  日期：2016.1

  The crystal structure of 3-deoxy-D-manno-octulosonate-8-phosphate synthase (KDO8PS) from Helicobacter pylori (HpKDO8PS) was determined alone and within various complexes, revealing an extra helix (HE) that is absent in the structures of KDO8PS from other organisms. In contrast to the metal coordination of the KDO8PS enzyme from Aquifex aeolicus, HpKDO8PS is specifically coordinated with Cd2+ or Zn2+ ions, and isothermal titration calorimetry (ITC) and differential scanning fluorimetry (DSF) revealed that Cd2+ thermally stabilizes the protein structure more efficiently than Zn2+. In the substrate bound structure, water molecules play a key role in fixing residues in the proper configuration to achieve a compact structure. Using the structures of HpKDO8PS and API [arabinose 5 -phosphate (A5P) and phosphoenolpyruvate (PEP) bisubstrate inhibitor], we generated 21 compounds showing potential HpKDO8PS-binding properties via in silico virtual screening. The capacity of three, avicularin, hyperin, and MC181, to bind to HpKDO8PS was confirmed through saturation transfer difference (STD) experiments, and we identified their specific ligand binding modes by combining competition experiments and docking simulation analysis. Hyperin was confirmed to bind to the A5P binding site, primarily via hydrophilic interaction, whereas MC181 bound to both the PEP and A5P binding sites through hydrophilic and hydrophobic interactions. These results were consistent with the epitope mapping by STD. Our results are expected to provide clues for the development of HpKDO8PS inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Structure−Activity Relationship Studies of Novel 4-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-1-(3-phenylpropyl)piperidine Analogs:  Synthesis and Biological Evaluation at the Dopamine and Serotonin Transporter Sites
  作者：Aloke K. Dutta、Cen Xu、Maarten E. A. Reith

  DOI：10.1021/jm9506581

  日期：1996.1.1

  Several analogs of the potent dopamine (DA) transporter ligand 4-[2-[bis(4-fluorophenyl)-methoxy]ethyl]-1-(3-phenylpropyl)piperidine, 1b, were made and biologically evaluated for their binding at the DA and serotonin (5HT) transporters in rat striatal membranes. Different alkyl chain lengths and substitutions were introduced in these molecules to generate an optimum activity and selectivity for the

  制备了强效多巴胺（DA）转运蛋白配体4- [2- [双（4-氟苯基）-甲氧基]乙基] -1-（3-苯基丙基）哌啶的类似物1b，并对其在生物学上的结合进行了生物学评估。大鼠纹状体膜中的DA和血清素（5HT）转运蛋白。在这些分子中引入了不同的烷基链长度和取代基，以产生针对DA转运蛋白的最佳活性和选择性。通常，未取代的和氟取代的化合物对于DA转运蛋白是最活跃和最具选择性的。化合物4- [2-（二苯基甲氧基）乙基] -1-苄基哌啶9a显示出高效价，并且在该系列化合物中对DA转运蛋白的选择性最高（5HT / DA = 49）。发现其中一些新颖的类似物比原始GBR 12909分子在DA转运蛋白上的结合更具选择性，
• Cignarella; Villa; Barlocco, Il Farmaco, 1993, vol. 48, # 10, p. 1439 - 1445
  作者：Cignarella、Villa、Barlocco

  DOI：——

  日期：——