ethyl 6-(3-chloropropoxy)quinoline-2-carboxylate | 1182723-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 6-(3-chloropropoxy)quinoline-2-carboxylate
• CAS: 1182723-52-9
• 化学式: C₁₅H₁₆ClNO₃
• 分子量: 293.75
• InChiKey: ATUVGJJUKSYUIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  哌啶 、 ethyl 6-(3-chloropropoxy)quinoline-2-carboxylate 在 potassium carbonate 作用下， 以70%的产率得到6-(3-piperidin-1-yl-propoxy)-quinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Selective naphthalene H3 receptor inverse agonists with reduced potential to induce phospholipidosis and their quinoline analogs

  摘要：

  We reported earlier the refinement of our initial. ve-point pharmacophore model for the Histamine 3 receptor (H3R), with a new acceptor feature important for binding and selectivity against the other histamine receptor subtypes 1, 2 and 4. This approach was validated with a new series of H3R inverse agonists: the naphthalene series. In this Letter, we describe our efforts to overcome the phospholipidosis flag identified with our initial lead compound (1a). During the optimization process, we monitored the potency of our molecules toward the H-3 receptor, their selectivity against H1R, H2R and H4R, as well as some key molecular properties that may influence phospholipidosis.Encouraged by the promising pro. le of the naphthalene series, we used our deeper understanding of the H3R pharmacophore model to lead us towards the quinoline series. This series is perceived to have intrinsic advantages with respect to its amphiphilic vector. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.100
• 作为产物：
  描述：

  6-hydroxy-quinoline-2-carboxylic acid ethyl ester 、 1-溴-3-氯丙烷 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 以90%的产率得到ethyl 6-(3-chloropropoxy)quinoline-2-carboxylate
  参考文献：
  名称：

  Selective naphthalene H3 receptor inverse agonists with reduced potential to induce phospholipidosis and their quinoline analogs

  摘要：

  We reported earlier the refinement of our initial. ve-point pharmacophore model for the Histamine 3 receptor (H3R), with a new acceptor feature important for binding and selectivity against the other histamine receptor subtypes 1, 2 and 4. This approach was validated with a new series of H3R inverse agonists: the naphthalene series. In this Letter, we describe our efforts to overcome the phospholipidosis flag identified with our initial lead compound (1a). During the optimization process, we monitored the potency of our molecules toward the H-3 receptor, their selectivity against H1R, H2R and H4R, as well as some key molecular properties that may influence phospholipidosis.Encouraged by the promising pro. le of the naphthalene series, we used our deeper understanding of the H3R pharmacophore model to lead us towards the quinoline series. This series is perceived to have intrinsic advantages with respect to its amphiphilic vector. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.100