3-(2-氨基乙基)-5-(苄氧基)-2-甲基吲哚 | 18658-09-8

• 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: 3-(2-氨基乙基)-5-(苄氧基)-2-甲基吲哚
• 英文名称: 3-(2-aminoethyl)-5-(benzyloxy)-2-methylindole
• 英文别名: 2-(5-(benzyloxy)-2-methyl-1H-indol-3-yl)ethylamine；5-Benzyloxy-2-methyl-tryptamin；3-(2-Amino-ethyl)-5-benzyloxy-2-methyl-indol；2-(5-benzyloxy-2-methyl-indol-3-yl)-ethylamine；2-(5-Benzyloxy-2-methyl-indol-3-yl)-aethylamin；2-(5-Benzyloxy-2-methyl-1H-indol-3-yl)-ethylamine；2-(2-methyl-5-phenylmethoxy-1H-indol-3-yl)ethanamine
• CAS: 18658-09-8
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: GXWTUBXFAHMHIY-UHFFFAOYSA-N

物化性质

• 沸点：
  489.7±40.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  3-(2-氨基乙基)-5-(苄氧基)-2-甲基吲哚 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 2-甲基-5-羟基色氨酸盐酸
  参考文献：
  名称：

  5-HT1 and 5-HT2 binding profiles of the serotonergic agents .alpha.-methylserotonin and 2-methylserotonin

  摘要：

  alpha-Methyl-5-hydroxytryptamine (alpha-Me-5-HT; 2) and 2-methyl-5-hydroxytryptamine (2-Me-5-HT; 3) are considered to be 5-HT2-selective and 5-HT3-selective agents, respectively. These agents were synthesized and examined at serotonin (5-HT) binding sites because there is relatively little documentation as to their selectivity and because they have not been previously examined at the newly discovered 5-HT1D and 5-HT1E sites. As previously reported, 2-Me-5-HT possesses a low affinity (Ki greater than 500 nM) for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT2 sites; this agent also displays a low affinity for 5-HT1D (Ki = 1220 nM) and 5-HT1E (Ki greater than 10,000 nM) sites. However, alpha-Me-5-HT displays little selectivity for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT1D sites (Ki = 42, 85, 150, and 150 nM, respectively) and a very low affinity for 5-HT1E (Ki greater than 10,000 nM) sites. Depending upon the radioligand used to label the sites, alpha-Me-5-HT displays either a low affinity (Ki = 880 nM with [3H]ketanserin) or a high affinity (Ki = 3 nM with [3H]DOB) for 5-HT2 sites. These results suggest that alpha-Me-5-HT is not as selective as previously considered and that caution should be used when employing this agent in pharmacological studies because it may act as mixed 5-HT1/5-HT2 agonist.

  DOI：

  10.1021/jm00164a046
• 作为产物：
  描述：

  5-苄氧基-2-甲基-吲哚 在 ammonium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 101.0h， 生成 3-(2-氨基乙基)-5-(苄氧基)-2-甲基吲哚
  参考文献：
  名称：

  5-HT1 and 5-HT2 binding profiles of the serotonergic agents .alpha.-methylserotonin and 2-methylserotonin

  摘要：

  alpha-Methyl-5-hydroxytryptamine (alpha-Me-5-HT; 2) and 2-methyl-5-hydroxytryptamine (2-Me-5-HT; 3) are considered to be 5-HT2-selective and 5-HT3-selective agents, respectively. These agents were synthesized and examined at serotonin (5-HT) binding sites because there is relatively little documentation as to their selectivity and because they have not been previously examined at the newly discovered 5-HT1D and 5-HT1E sites. As previously reported, 2-Me-5-HT possesses a low affinity (Ki greater than 500 nM) for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT2 sites; this agent also displays a low affinity for 5-HT1D (Ki = 1220 nM) and 5-HT1E (Ki greater than 10,000 nM) sites. However, alpha-Me-5-HT displays little selectivity for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT1D sites (Ki = 42, 85, 150, and 150 nM, respectively) and a very low affinity for 5-HT1E (Ki greater than 10,000 nM) sites. Depending upon the radioligand used to label the sites, alpha-Me-5-HT displays either a low affinity (Ki = 880 nM with [3H]ketanserin) or a high affinity (Ki = 3 nM with [3H]DOB) for 5-HT2 sites. These results suggest that alpha-Me-5-HT is not as selective as previously considered and that caution should be used when employing this agent in pharmacological studies because it may act as mixed 5-HT1/5-HT2 agonist.

  DOI：

  10.1021/jm00164a046

文献信息

• [EN] BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION<br/>[FR] TRAITEMENT MÉDICAMENTEUX ET PANEL DE BIOMARQUEURS CIBLANT DES MALADIES DUES À L'ONTOLOGIE MULTIFACTORIELLE DE L'INTERRUPTION DE LA GLYCOCALYX
  申请人：ARTEREZ INC

  公开号：WO2021062298A1

  公开（公告）日：2021-04-01

  The present disclosure provides biomarkers useful as companion diagnostics for detecting glycocalyx-based disease that is amenable to treatment using compounds designed for improving the condition of the glycocalyx and/or reducing inflammation and/or oxidative damage, as well as related compositions, kits, and methods.

  本公开提供了作为伴随诊断的生物标志物，用于检测适用于使用旨在改善糖类壁和/或减少炎症和/或氧化损伤状况的化合物治疗的基于糖类壁的疾病，以及相关的组合物、试剂盒和方法。
• 一种吲哚类衍生物及其合成方法
  申请人：南通大学

  公开号：CN111892527B

  公开（公告）日：2022-06-28

  本发明属于有机合成技术领域，涉及一种(Z)‑4‑((2‑(5‑(苄氧基)‑2‑甲基‑1H‑吲哚‑3‑基)乙基亚氨基(苯基)甲基)‑1,3‑苯二酚及其合成方法。本发明提供的合成方法为：以1‑(4‑(苄氧基)苯基)肼盐酸盐为原料，经胺甲基化、氨解、还原以及取代反应四步反应制备了(Z)‑4‑((2‑(5‑(苄氧基)‑2‑甲基‑1H‑吲哚‑3‑基)乙基亚氨基(苯基)甲基)‑1,3‑苯二酚，为该吲哚类衍生物的合成提供了一种高效合成的方法。
• Synthesis and biological activity of isoalantolactone—tryptamine conjugates
  作者：S. G. Klochkov、S. V. Afanas’eva、Yu. N. Bulychev、M. E. Neganova、E. F. Shevtsova

  DOI：10.1007/s11172-012-0058-x

  日期：2012.2

  Previously unknown adducts of substituted tryptamines with sesquiterpene lactones, viz., isoalantolactone and its epoxy derivative, were synthesized by the Michael reaction. The compounds obtained were tested for various types of biological activity.

  以前未知的取代色胺与倍半萜内酯的加合物，即异戊内酯及其环氧衍生物，是通过迈克尔反应合成的。测试获得的化合物的各种类型的生物活性。
• The Synthesis of Tryptamines Related to Serotonin
  作者：Elliott Shaw

  DOI：10.1021/ja01621a042

  日期：1955.8
• 5-HT1 and 5-HT2 binding profiles of the serotonergic agents .alpha.-methylserotonin and 2-methylserotonin
  作者：Abd M. Ismaiel、Milt Titeler、Keith J. Miller、Thomas S. Smith、Richard A. Glennon

  DOI：10.1021/jm00164a046

  日期：1990.2

  alpha-Methyl-5-hydroxytryptamine (alpha-Me-5-HT; 2) and 2-methyl-5-hydroxytryptamine (2-Me-5-HT; 3) are considered to be 5-HT2-selective and 5-HT3-selective agents, respectively. These agents were synthesized and examined at serotonin (5-HT) binding sites because there is relatively little documentation as to their selectivity and because they have not been previously examined at the newly discovered 5-HT1D and 5-HT1E sites. As previously reported, 2-Me-5-HT possesses a low affinity (Ki greater than 500 nM) for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT2 sites; this agent also displays a low affinity for 5-HT1D (Ki = 1220 nM) and 5-HT1E (Ki greater than 10,000 nM) sites. However, alpha-Me-5-HT displays little selectivity for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT1D sites (Ki = 42, 85, 150, and 150 nM, respectively) and a very low affinity for 5-HT1E (Ki greater than 10,000 nM) sites. Depending upon the radioligand used to label the sites, alpha-Me-5-HT displays either a low affinity (Ki = 880 nM with [3H]ketanserin) or a high affinity (Ki = 3 nM with [3H]DOB) for 5-HT2 sites. These results suggest that alpha-Me-5-HT is not as selective as previously considered and that caution should be used when employing this agent in pharmacological studies because it may act as mixed 5-HT1/5-HT2 agonist.