2-(5-甲氧基-1H-吲哚-3-基)丙烷-1-胺 | 20731-70-8

• 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
• 中文名称: 2-(5-甲氧基-1H-吲哚-3-基)丙烷-1-胺
• 英文名称: 5-methoxy-α-methyltryptamine
• 英文别名: 2-(5-methoxy-indol-3-yl)-propylamine；5-Methoxy-β-methyl-tryptamin；5-Methoxy-beta-methyltryptamine；2-(5-methoxy-1H-indol-3-yl)propan-1-amine
• CAS: 20731-70-8
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: PLKJXFPRSHOODN-UHFFFAOYSA-N

物化性质

• 沸点：
  375.6±27.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-(5-甲氧基-1H-吲哚-3-基)丙烷-1-胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Beta-Methylmelatonin
  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 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 sodium hydride 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 25.75h， 生成 2-(5-甲氧基-1H-吲哚-3-基)丙烷-1-胺
  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

• Beta-alkylmelatonins
  申请人：ELI LILLY AND COMPANY

  公开号：EP0281242A1

  公开（公告）日：1988-09-07

  β-Alkylmelatonins are useful as ovulation inhibitors.

  β-烷基褪黑激素可作为排卵抑制剂。
• Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
  作者：John I. Trujillo、Marvin J. Meyers、David R. Anderson、Shridhar Hegde、Matthew W. Mahoney、William F. Vernier、Ingrid P. Buchler、Kun K. Wu、Syaluan Yang、Susan J. Hartmann、David B. Reitz

  DOI：10.1016/j.bmcl.2007.05.070

  日期：2007.8

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.
• US4997845A
  申请人：——

  公开号：US4997845A

  公开（公告）日：1991-03-05
• 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.