1-cyano-1-(5-methoxy-1-methyl-1H-indol-3-yl)cyclopropane | 339094-34-7

• 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-cyano-1-(5-methoxy-1-methyl-1H-indol-3-yl)cyclopropane
• 英文别名: 1-(5-Methoxy-1-methylindol-3-yl)cyclopropane-1-carbonitrile；1-(5-methoxy-1-methylindol-3-yl)cyclopropane-1-carbonitrile
• CAS: 339094-34-7
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: LUFFAWGQJOSMNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-cyano-1-(5-methoxy-1-methyl-1H-indol-3-yl)cyclopropane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 1.0h， 生成 1-[1-(5-methoxy-1-methyl-1H-indol-3-yl)cyclopropyl]methanamine
  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：

  5-甲氧基吲哚-3-甲醛 在 氢氧化钾 、 双(三甲基硅烷基)氨基钾 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.05h， 生成 1-cyano-1-(5-methoxy-1-methyl-1H-indol-3-yl)cyclopropane
  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

文献信息

• A New Ring-Forming Methodology for the Synthesis of Conformationally Constrained Bioactive Molecules
  作者：Demetris P. Papahatjis、Spyros Nikas、Andrew Tsotinis、Margarita Vlachou、Alexandros Makriyannis

  DOI：10.1246/cl.2001.192

  日期：2001.3

  A new, general, one pot method for introducing carbocyclic rings alpha to a nitrile moiety is described. Treatment of readily available arylacetonitriles with potassium bis(trimethylsilyl)amide and subsequent alkylation with α, ω-dibromo or dichloroalkanes in tetrahydrofuran under anhydrous conditions at 0 °C produces cycloalkyl adducts in good yields and short reaction times.

  描述了一种新的通用一锅法，用于在腈基前引入碳环。将 readily available 的芳基乙腈与氨基钾双(trimethylsilyl)处理，随后在无水条件下于0 °C的四氢呋喃中与α,ω-二溴或二氯烷烃进行烷基化，可以在短反应时间内以良好的产率生成环烷基附加物。
• 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.