methyl 1-(6-azidohexyl)-6-(5-azidopentyloxy)indole-2-carboxylate | 502936-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 1-(6-azidohexyl)-6-(5-azidopentyloxy)indole-2-carboxylate
• CAS: 502936-97-2
• 化学式: C₂₁H₂₉N₇O₃
• 分子量: 427.506
• InChiKey: NRPWFXVAOCMYHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  31.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  137.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 1-(6-azidohexyl)-6-(5-azidopentyloxy)indole-2-carboxylate 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 、 苄基三甲基氢氧化铵 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 109.5h， 生成 N-{(2S)-1-[(2-hydroxycarbonyl)-2-adamantylamino]-3-(4-hydroxyphenyl)-1-oxo-propan-2-yl} 1-(6-guanidinohexyl)-6-(5-guanidinopentyloxy)indole-2-carboxamide bis(trifluoroacetate)
  参考文献：
  名称：

  Synthesis and Biological Studies of Novel Neurotensin(8–13) Mimetics

  摘要：

  Novel neurotensin (NT) (8-13) (Arg(8)-Arg(9)-Pro(10)-Tyr(11)-Ile(12)-Leu(13)) mimetics 3, 4 were designed by adopting all intrinsic functional groups of the native neurotensin(8-13) and using a substituted indole as a template to mimic the pharmacophore of NT(8-13). Biological studies at subtype 1 of the NT receptor showed that 3 has a 55 and 580 nM binding affinity at rat and human neurotensin receptors, respectively, As a comparison. compounds 5 and 6 were also synthesized. The binding difference between 3, 4 and 5, 6 argues the importance of the carboxylic group in achieving higher potency NT(8-13) mimetics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00342-5
• 作为产物：
  描述：

  methyl 2-azido-3-{4-[5-(tert-butyldimethylsilyloxy)pentyloxy]phenyl}propenoate 在 18-冠醚-6 、 三(2-氯乙基)胺 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 methyl 1-(6-azidohexyl)-6-(5-azidopentyloxy)indole-2-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Studies of Novel Neurotensin(8–13) Mimetics

  摘要：

  Novel neurotensin (NT) (8-13) (Arg(8)-Arg(9)-Pro(10)-Tyr(11)-Ile(12)-Leu(13)) mimetics 3, 4 were designed by adopting all intrinsic functional groups of the native neurotensin(8-13) and using a substituted indole as a template to mimic the pharmacophore of NT(8-13). Biological studies at subtype 1 of the NT receptor showed that 3 has a 55 and 580 nM binding affinity at rat and human neurotensin receptors, respectively, As a comparison. compounds 5 and 6 were also synthesized. The binding difference between 3, 4 and 5, 6 argues the importance of the carboxylic group in achieving higher potency NT(8-13) mimetics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00342-5