1-(5-methoxy-1H-indol-3-yl)cyclobutanecarbonitrile | 896101-84-1

• 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: 1-(5-methoxy-1H-indol-3-yl)cyclobutanecarbonitrile
• 英文别名: 1-(5-methoxy-1H-indol-3-yl)cyclobutane-1-carbonitrile
• CAS: 896101-84-1
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: HLPJKYDJSCIYHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-methoxy-1H-indol-3-yl)cyclobutanecarbonitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 1.0h， 生成 C-[1-(5-Methoxy-1H-indol-3-yl)-cyclobutyl]-methylamine
  参考文献：
  名称：

  Mapping the Melatonin Receptor. 7. Subtype Selective Ligands Based on β-Substituted N-Acyl-5-methoxytryptamines and β-Substituted N-Acyl-5-methoxy-1-methyltryptamines

  摘要：

  A series of beta-substituted and beta,beta-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxy-tryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT(1) and MT(2) receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. beta-Methylmelatonin ( 17a) and beta,beta-dimethylmelatonin ( 17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus. N-Butanoyl 5-methoxy-1-methyl-beta,beta-trimethylenetryptamine ( 12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-beta,beta-tetramethylenetryptamine ( 13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.

  DOI：

  10.1021/jm0512544
• 作为产物：
  描述：

  N-ethyl-N-((5-methoxy-1H-indol-3-yl)methyl)ethylamine 在 4-二甲氨基吡啶 、 sodium hydride 、 三氟乙酸 、 碘甲烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 38.0h， 生成 1-(5-methoxy-1H-indol-3-yl)cyclobutanecarbonitrile
  参考文献：
  名称：

  The discovery of carboline analogs as potent MAPKAP-K2 inhibitors

  摘要：

  The discovery of a series of potent, carboline-based MK2 inhibitors is described. These compounds inhibit MK2 with IC(50)s as low as 10 nM, as measured in a DELFIA assay. An X-ray crystal structure reveals that they bind in a region near the p-loop and the hinge region of MK2a. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.101

文献信息

• Mapping the Melatonin Receptor. 7. Subtype Selective Ligands Based on β-Substituted <i>N</i>-Acyl-5-methoxytryptamines and β-Substituted <i>N</i>-Acyl-5-methoxy-1-methyltryptamines
  作者：Andrew Tsotinis、Margarita Vlachou、Demetris P. Papahatjis、Theodora Calogeropoulou、Spyros P. Nikas、Peter J. Garratt、Vincent Piccio、Stefan Vonhoff、Kathryn Davidson、Muy-Teck Teh、David Sugden

  DOI：10.1021/jm0512544

  日期：2006.6.1

  A series of beta-substituted and beta,beta-disubstituted N-acyl 5-methoxy-1-methyltryptamines and 5-methoxy-tryptamines have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human MT(1) and MT(2) receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency of all analogues was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. beta-Methylmelatonin ( 17a) and beta,beta-dimethylmelatonin ( 17b), though showing a slight decrease in binding at human receptors, show an increase in potency on Xenopus. N-Butanoyl 5-methoxy-1-methyl-beta,beta-trimethylenetryptamine ( 12c) is an antagonist at human MT1 receptors but an agonist at MT2, while N-butanoyl 5-methoxy-1-methyl-beta,beta-tetramethylenetryptamine ( 13c) is an antagonist at MT1 but had no action at MT2 and is one of the first examples of an MT1 selective antagonist.
• The discovery of carboline analogs as potent MAPKAP-K2 inhibitors
  作者：Jiang-Ping Wu、Ji Wang、Asitha Abeywardane、Denise Andersen、Michel Emmanuel、Elda Gautschi、Daniel R. Goldberg、Mohammed A. Kashem、Susan Lukas、Wang Mao、Leslie Martin、Tina Morwick、Neil Moss、Christopher Pargellis、Usha R. Patel、Lori Patnaude、Gregory W. Peet、Donna Skow、Roger J. Snow、Yancey Ward、Brian Werneburg、Andre White

  DOI：10.1016/j.bmcl.2007.05.101

  日期：2007.8

  The discovery of a series of potent, carboline-based MK2 inhibitors is described. These compounds inhibit MK2 with IC(50)s as low as 10 nM, as measured in a DELFIA assay. An X-ray crystal structure reveals that they bind in a region near the p-loop and the hinge region of MK2a. (c) 2007 Elsevier Ltd. All rights reserved.