7-iodo-3-methoxy-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide | 765296-49-9

• 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: 7-iodo-3-methoxy-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide
• CAS: 765296-49-9
• 化学式: C₂₆H₂₃IN₂O₂
• 分子量: 522.385
• InChiKey: PHFHTNWKVOXWEN-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-iodo-3-methoxy-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以67%的产率得到3-Hydroxy-7-iodo-2-phenyl-quinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide
  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
• 作为产物：
  描述：

  2-甲氧基苯乙酮 在 盐酸 、 氢氧化钾 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.0h， 生成 7-iodo-3-methoxy-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-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