2-Methyl-8-methoxypiperazino<1,2-a>indol | 35727-28-7

• 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: 2-Methyl-8-methoxypiperazino<1,2-a>indol
• 英文别名: 8-methoxy-2-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole；8-Methoxy-2-methyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole；8-methoxy-2-methyl-3,4-dihydro-1H-pyrazino[1,2-a]indole
• CAS: 35727-28-7
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: IHPWGGAJSLAGJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  n,n-二甲基亚甲基碘化胺 、 2-Methyl-8-methoxypiperazino<1,2-a>indol 在 氨 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 1-(8-methoxy-2-methyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indol-10-yl)-N,N-dimethylmethanamine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands

  摘要：

  Two novel series of melatonin-derived compounds have been synthesized and pharmacologically evaluated at the MT1 and MT2 subtypes of melatonin receptors. Compounds 12b-c are non-selective high-affinity MT1 and MT2 receptor ligands (K-i = 7-11 nM). Compound 12b had little intrinsic activity at the MT1 receptor and no intrinsic activity at the MT2 receptor. Compound 20d displayed the highest MT2 binding affinity (K-i = 2 nM) and moderate selectivity toward the MT2 subtype (K-i MT1/MT2 ratio = 8) behaving as MT2 antagonist and MT1 agonist (IC50 = 112 pM). The findings help define SARs around the positions 1 and 2 of melatonin with respect to binding affinity, MT2 selectivity, and intrinsic activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.068
• 作为产物：
  描述：

  benzyl 8-methoxy-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以96%的产率得到2-Methyl-8-methoxypiperazino<1,2-a>indol
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands

  摘要：

  Two novel series of melatonin-derived compounds have been synthesized and pharmacologically evaluated at the MT1 and MT2 subtypes of melatonin receptors. Compounds 12b-c are non-selective high-affinity MT1 and MT2 receptor ligands (K-i = 7-11 nM). Compound 12b had little intrinsic activity at the MT1 receptor and no intrinsic activity at the MT2 receptor. Compound 20d displayed the highest MT2 binding affinity (K-i = 2 nM) and moderate selectivity toward the MT2 subtype (K-i MT1/MT2 ratio = 8) behaving as MT2 antagonist and MT1 agonist (IC50 = 112 pM). The findings help define SARs around the positions 1 and 2 of melatonin with respect to binding affinity, MT2 selectivity, and intrinsic activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.068

文献信息

• [a]-FUSED INDOLE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES
  申请人：Ayral-Kaloustian Semiramis

  公开号：US20090192147A1

  公开（公告）日：2009-07-30

  The invention relates to [a]-fused indole compounds of the Formula II, or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein. The invention also relates to compositions comprising the compounds of Formula II, and methods for making and using the compounds.

  该发明涉及Formula II的[a]-融合吲哚化合物，或其药用可接受的盐，其中组成变量如本文所定义。该发明还涉及包含Formula II化合物的组合物，以及制备和使用这些化合物的方法。
• [EN] [A]-FUSED INDOLE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES<br/>[FR] COMPOSÉS D'INDOLE FONDUS-[A], LEUR UTILISATION EN TANT QU'INHIBITEURS DE MTOR KINASE ET DE PI3 KINASE, ET LEURS SYNTHÈSES
  申请人：WYETH CORP

  公开号：WO2009097515A2

  公开（公告）日：2009-08-06

  The invention relates to [a]-fused indole compounds of the Formula II, or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein. The invention also relates to compositions comprising the compounds of Formula II, and methods for making and using the compounds.
• Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands
  作者：Christian Markl、Mohamed I. Attia、Justin Julius、Shalini Sethi、Paula A. Witt-Enderby、Darius P. Zlotos

  DOI：10.1016/j.bmc.2009.04.068

  日期：2009.7

  Two novel series of melatonin-derived compounds have been synthesized and pharmacologically evaluated at the MT1 and MT2 subtypes of melatonin receptors. Compounds 12b-c are non-selective high-affinity MT1 and MT2 receptor ligands (K-i = 7-11 nM). Compound 12b had little intrinsic activity at the MT1 receptor and no intrinsic activity at the MT2 receptor. Compound 20d displayed the highest MT2 binding affinity (K-i = 2 nM) and moderate selectivity toward the MT2 subtype (K-i MT1/MT2 ratio = 8) behaving as MT2 antagonist and MT1 agonist (IC50 = 112 pM). The findings help define SARs around the positions 1 and 2 of melatonin with respect to binding affinity, MT2 selectivity, and intrinsic activity. (C) 2009 Elsevier Ltd. All rights reserved.