3-(5-methoxy-1H-indol-2-yl)propan-1-ol

• 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: 3-(5-methoxy-1H-indol-2-yl)propan-1-ol
• 英文别名: 5-methoxy-1H-2-indolepropanol
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: WGBUQECRQBMQST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-methoxy-1H-indol-2-yl)propan-1-ol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 22.0h， 以38%的产率得到2-(3-bromopropyl)-5-methoxy-1H-indole
  参考文献：
  名称：

  Design, Synthesis, and Melatoninergic Activity of New Azido- and Isothiocyanato-Substituted Indoles

  摘要：

  To develop irreversibly binding ligands for the melatonin receptor(s) as tools for tracing the primary melatonin binding site, we report on the design and synthesis of new melatoninergic azido- and isothiocyanato-substituted indoles. All active compounds were partial agonists or antagonists in the Xenopus melanophore assay, the most potent being the 5-OMe C3-substituted azido 45 and isothiocyanato 46 analogues.

  DOI：

  10.1021/jm7010723
• 作为产物：
  描述：

  5-甲氧基-1H-吲哚-2-羧酸 在 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、241.32 kPa 条件下， 反应 25.0h， 生成 3-(5-methoxy-1H-indol-2-yl)propan-1-ol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Indolyl-Pyridinyl-Propenones Having Either Methuosis or Microtubule Disruption Activity

  摘要：

  Methuosis is a form of nonapoptotic cell death characterized by an accumulation of macropinosome-derived vacuoles with eventual loss of membrane integrity. Small molecules inducing methuosis could offer significant advantages compared to more traditional anticancer drug therapies that typically rely on apoptosis. Herein we further define the effects of chemical substitutions at the 2- and 5-indolyl positions on our lead compound 3-(5-methoxy-2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propene-1-one (MOMIPP). We have identified a number of compounds that induce methuosis at similar potencies, including an interesting analogue having a hydroxypropyl substituent at the 2-position. In addition, we have discovered that certain substitutions on the 2-indolyl position redirect the mode of cytotoxicity from methuosis to microtubule disruption. This switch in activity is associated with an increase in potency as large as 2 orders of magnitude. These compounds appear to represent a new class of potent microtubule-active anticancer agents.

  DOI：

  10.1021/jm501997q

文献信息

• Materials And Methods Useful To Induce Vacuolization, Cell Death, Or A Combination Thereof
  申请人：The University of Toledo

  公开号：US20150152049A1

  公开（公告）日：2015-06-04

  The present invention provides materials and methods to induce cell death by methuosis, a non-apoptotic cell death mechanism, to induce vacuolization without cell death, or to induce cell death without vacuolization. Small molecules herein are useful for treating cell proliferation disorders or anomalies, particularly, but not exclusively, cancer. Methods related to the research and pharmaceutical use of the small molecules are also provided herein.

  本发明提供了诱导细胞通过非凋亡性细胞死亡机制methuosis死亡、诱导产生空泡而不导致细胞死亡，或诱导细胞死亡而不产生空泡的材料和方法。本文中的小分子可用于治疗细胞增殖异常或疾病，尤其是癌症。本文还提供了与小分子相关的研究和制药方法。
• US9061994B1
  申请人：——

  公开号：US9061994B1

  公开（公告）日：2015-06-23
• Design, Synthesis, and Melatoninergic Activity of New Azido- and Isothiocyanato-Substituted Indoles
  作者：Andrew Tsotinis、Pandelis A. Afroudakis、Kathryn Davidson、Anjali Prashar、David Sugden

  DOI：10.1021/jm7010723

  日期：2007.12.13

  To develop irreversibly binding ligands for the melatonin receptor(s) as tools for tracing the primary melatonin binding site, we report on the design and synthesis of new melatoninergic azido- and isothiocyanato-substituted indoles. All active compounds were partial agonists or antagonists in the Xenopus melanophore assay, the most potent being the 5-OMe C3-substituted azido 45 and isothiocyanato 46 analogues.
• Synthesis and Biological Evaluation of Indolyl-Pyridinyl-Propenones Having Either Methuosis or Microtubule Disruption Activity
  作者：Christopher J. Trabbic、Jean H. Overmeyer、Evan M. Alexander、Emily J. Crissman、Heather M. Kvale、Marcie A. Smith、Paul W. Erhardt、William A. Maltese

  DOI：10.1021/jm501997q

  日期：2015.3.12

  Methuosis is a form of nonapoptotic cell death characterized by an accumulation of macropinosome-derived vacuoles with eventual loss of membrane integrity. Small molecules inducing methuosis could offer significant advantages compared to more traditional anticancer drug therapies that typically rely on apoptosis. Herein we further define the effects of chemical substitutions at the 2- and 5-indolyl positions on our lead compound 3-(5-methoxy-2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propene-1-one (MOMIPP). We have identified a number of compounds that induce methuosis at similar potencies, including an interesting analogue having a hydroxypropyl substituent at the 2-position. In addition, we have discovered that certain substitutions on the 2-indolyl position redirect the mode of cytotoxicity from methuosis to microtubule disruption. This switch in activity is associated with an increase in potency as large as 2 orders of magnitude. These compounds appear to represent a new class of potent microtubule-active anticancer agents.