N-[2-(9-methoxy-2-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indol-11-yl)ethyl]acetamide | 1174915-24-2

• 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-(9-methoxy-2-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indol-11-yl)ethyl]acetamide
• 英文别名: N-[2-(9-methoxy-2-methyl-1,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-11-yl)ethyl]acetamide
• CAS: 1174915-24-2
• 化学式: C₁₈H₂₅N₃O₂
• 分子量: 315.415
• InChiKey: AJXXAUPRLYVAPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-(2-((benzyl(methyl)amino)methyl)-1-(2-cyanoethyl)-5-methoxy-1H-indol-3-yl)ethyl)acetamide 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 20.0 ℃ 、700.01 Pa 条件下， 反应 48.0h， 以41%的产率得到N-[2-(9-methoxy-2-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indol-11-yl)ethyl]acetamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands

  摘要：

  Two novel series of melatonin-derived compounds have been synthesized and pharmacologically evaluated at the MT1 and MT2 subtypes of melatonin receptors. Compounds 12b-c are non-selective high-affinity MT1 and MT2 receptor ligands (K-i = 7-11 nM). Compound 12b had little intrinsic activity at the MT1 receptor and no intrinsic activity at the MT2 receptor. Compound 20d displayed the highest MT2 binding affinity (K-i = 2 nM) and moderate selectivity toward the MT2 subtype (K-i MT1/MT2 ratio = 8) behaving as MT2 antagonist and MT1 agonist (IC50 = 112 pM). The findings help define SARs around the positions 1 and 2 of melatonin with respect to binding affinity, MT2 selectivity, and intrinsic activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.068