(S)-3-hydroxy-2-(4-methoxyphenyl)-N-(1-phenylpropyl)quinoline-4-carboxamide

• 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)-3-hydroxy-2-(4-methoxyphenyl)-N-(1-phenylpropyl)quinoline-4-carboxamide
• 英文别名: (s)-3-hydroxy-2-(4-methoxyphenyl)-N-(1-phenylpropyl)quinoline-4-carboxamide；3-hydroxy-2-(4-methoxyphenyl)-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide
• 化学式: C₂₆H₂₄N₂O₃
• 分子量: 412.488
• InChiKey: AUTRFZGWSIKOKS-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 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：
  71.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-hydroxy-2-(4-methoxyphenyl)-N-(1-phenylpropyl)quinoline-4-carboxamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以57%的产率得到(S)-3-hydroxy-2-(4-hydroxyphenyl)-N-(1-phenylpropyl)quinoline-4-carboxamide
  参考文献：
  名称：

  Development of novel NK3 receptor antagonists with reduced environmental impact

  摘要：

  The neurokinin B (NKB)-neurokinin-3 receptor (NK3R) signaling positively regulates the release of gonadotropin-releasing hormone (GnRH) from the hypothalamus. The NK3R-selective antagonists may suppress the reproductive functions of mammals. For development of novel NK3R antagonists with reduced environmental toxicity, a structure-activity relationship study of an NK3R antagonist, talnetant, was carried out. Among several talnetant derivatives with labile functional groups in the natural environment, 3-mercaptoquinoline 2f exhibited a comparable biological activity to that of the parent talnetant. Additionally, compound 2f was converted into the disulfide 3f or isothiazolone 8 by air-oxidation, both of which showed no binding affinity to NK3R. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.054
• 作为产物：
  描述：

  2-(4-甲氧基苯基)-2-氧代乙酸乙酯 在 三乙胺 、 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 (S)-3-hydroxy-2-(4-methoxyphenyl)-N-(1-phenylpropyl)quinoline-4-carboxamide
  参考文献：
  名称：

  Development of novel NK3 receptor antagonists with reduced environmental impact

  摘要：

  The neurokinin B (NKB)-neurokinin-3 receptor (NK3R) signaling positively regulates the release of gonadotropin-releasing hormone (GnRH) from the hypothalamus. The NK3R-selective antagonists may suppress the reproductive functions of mammals. For development of novel NK3R antagonists with reduced environmental toxicity, a structure-activity relationship study of an NK3R antagonist, talnetant, was carried out. Among several talnetant derivatives with labile functional groups in the natural environment, 3-mercaptoquinoline 2f exhibited a comparable biological activity to that of the parent talnetant. Additionally, compound 2f was converted into the disulfide 3f or isothiazolone 8 by air-oxidation, both of which showed no binding affinity to NK3R. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.054

文献信息

• Development of novel NK3 receptor antagonists with reduced environmental impact
  作者：Koki Yamamoto、Shiho Okazaki、Hiroaki Ohno、Fuko Matsuda、Satoshi Ohkura、Kei-ichiro Maeda、Nobutaka Fujii、Shinya Oishi

  DOI：10.1016/j.bmc.2016.05.054

  日期：2016.8

  The neurokinin B (NKB)-neurokinin-3 receptor (NK3R) signaling positively regulates the release of gonadotropin-releasing hormone (GnRH) from the hypothalamus. The NK3R-selective antagonists may suppress the reproductive functions of mammals. For development of novel NK3R antagonists with reduced environmental toxicity, a structure-activity relationship study of an NK3R antagonist, talnetant, was carried out. Among several talnetant derivatives with labile functional groups in the natural environment, 3-mercaptoquinoline 2f exhibited a comparable biological activity to that of the parent talnetant. Additionally, compound 2f was converted into the disulfide 3f or isothiazolone 8 by air-oxidation, both of which showed no binding affinity to NK3R. (C) 2016 Elsevier Ltd. All rights reserved.