N-[2-(7-{4-[3-(2-acetylaminoethyl)-1H-indol-5-yloxy]butoxy}-naphthalen-1-yl)-ethyl]acetamide | 1234180-19-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[2-(7-{4-[3-(2-acetylaminoethyl)-1H-indol-5-yloxy]butoxy}-naphthalen-1-yl)-ethyl]acetamide
• 英文别名: N-[2-(7-{4-[3-(2-Acetylaminoethyl)-1H-indol-5-yloxy]-butoxy}-naphthalen-1-yl)ethyl]acetamide；N-[2-[7-[4-[[3-(2-acetamidoethyl)-1H-indol-5-yl]oxy]butoxy]naphthalen-1-yl]ethyl]acetamide
• CAS: 1234180-19-8
• 化学式: C₃₀H₃₅N₃O₄
• 分子量: 501.626
• InChiKey: GNQUIGRVFLTMRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[2-(7-{4-[3-(2-acetylaminoethyl)-1-benzenesulfonyl-1H-indol-5-yloxy]butoxy}-naphthalen-1-yl)-ethyl]acetamide 在 氯化铵 、 magnesium 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以60%的产率得到N-[2-(7-{4-[3-(2-acetylaminoethyl)-1H-indol-5-yloxy]butoxy}-naphthalen-1-yl)-ethyl]acetamide
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel naphthalenic derivatives as selective MT1 melatoninergic ligands

  摘要：

  Novel heterodimer analogues of melatonin were synthesized, when agomelatine (1) and various aryl units are linked via a linear alkyl chain through the methoxy group. The compounds were tested for their actions at melatonin receptors. Several of these ligands are MT1-selective with nanomolar or subnanomolar affinity. In addition, while most of the derivatives behave as partial agonists on one or both receptor subtypes, N-[2-(7-{4-[6-(1-methoxycarbonylethyl)naphthalen-2-yloxy]butoxy}naphthalen-1-yl)ethyl]acetamide (36), a subnanomolar MT1 ligand with an 11-fold preference over MT2 receptors, is a full antagonist on both receptors. Our results also confirm that the selectivity seen for the MT1 receptor arises predominantly from steric factors and is not a consequence of the bridging of melatonin receptor dimers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.008