(S)-N-(1-phenylpropyl)-8-fluoro-3-methoxy-2-phenylquinoline-4-carboxamide | 681478-76-2

• 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: (S)-N-(1-phenylpropyl)-8-fluoro-3-methoxy-2-phenylquinoline-4-carboxamide
• CAS: 681478-76-2
• 化学式: C₂₆H₂₃FN₂O₂
• 分子量: 414.479
• InChiKey: GWJISOURXFHCCE-NRFANRHFSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  564.9±50.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-phenylpropyl)-8-fluoro-3-methoxy-2-phenylquinoline-4-carboxamide 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 以28%的产率得到8-Fluoro-7-iodo-3-methoxy-2-phenyl-quinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide
  参考文献：
  名称：

  Lithiation of Functionalized Fluoroquinolines:  Synthesis of Dihalo-2-phenylquinoline-4-carboxamides and in Vitro Evaluation as NK-3 Receptor Ligands for Medical Imaging Studies

  摘要：

  Fluoroioido-2-phenylquinoline-4-carboxamides, analogues of NK-3 antagonist SB 223412, were synthesized and evaluated as NK-3 ligands with the aim of developing radioligands suitable for both Positron Emission Tomography (PET) and Single Photon Emission Computed Tomography (SPECT) studies. The key step utilizes metalation directed by the fluorine atom for iodination of the quinoline ring.

  DOI：

  10.1021/jo0358426
• 作为产物：
  描述：

  2-甲氧基苯乙酮 在 盐酸 、 氢氧化钾 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 91.0h， 生成 (S)-N-(1-phenylpropyl)-8-fluoro-3-methoxy-2-phenylquinoline-4-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel fluoro and iodo quinoline carboxamides as potential ligands of NK-3 receptors for in vivo imaging studies

  摘要：

  In order to develop radioligands of human NK-3 receptor (hNK-3r) for imaging studies by positron emission tomography (PET) or single photon emission computed tomography (SPECT), a new series of fluoro- and iodo-quinoline carboxamides were synthesized and evaluated in a target receptor binding assay. Compared to the unsubstituted parent compound SB 223 412 (K-i = 27 nM +/- 9). affinity was not altered for the analogues 1c and 2c bearing a fluorine in position 8 (K-i similar to 24-27 nM), and was only slightly reduced for compounds 1b, 2b, 1c and 2e fluorinated or iodinated at the position 7 (K-i similar to 49-67 nM). A drastic reduction in binding (K-i > 115 nM) was observed for all other halogenated compounds 1a, 2a, 1d, 2d, 1f and 2f. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.020