5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine | 1443411-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine
• 英文别名: 5-Methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine；5-methoxy-1-methylpyrrolo[2,3-c]pyridine
• CAS: 1443411-48-0
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: NYPLZOIGBDJGQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine 在 aluminum (III) chloride 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 3-(benzofuran-3-yl)-4-(5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Characterization of Maleimide-Based Glycogen Synthase Kinase-3 (GSK-3) Inhibitors as Stimulators of Steroidogenesis

  摘要：

  Inhibition of GSK-3 beta has been well documented to account for the behavioral actions of the mood stabilizer lithium in various animal models of mood disorders. Recent studies have showed that genetic or pharmacological inhibition of GSK-3 beta resulted in anxiolytic-like and pro-social behavior. In our ongoing efforts to develop GSK-3 beta inhibitors for the treatment of mood disorders, SAR studies on maleimide-based compounds were undertaken. We present herein for the first time that some of these GSK-3 beta inhibitors, in particular analogues 1 and 9, were able to stimulate progesterone production in the MA-10 mouse tumor Leydig cell model of steroidogenesis without any significant toxicity. These two compounds were tested in the SmartCube behavioral assay and showed anxiolytic-like signatures following daily dose administration (50 mg/kg, ip) for 13 days. Taken together, these results support the hypothesis that GSK-3 beta inhibition could influence neuroactive steroid production thereby mediating the modulation of anxiety-like behavior in vivo.

  DOI：

  10.1021/jm400511s
• 作为产物：
  描述：

  5-甲基-6-氮杂吲哚 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine
  参考文献：
  名称：

  Characterization of Maleimide-Based Glycogen Synthase Kinase-3 (GSK-3) Inhibitors as Stimulators of Steroidogenesis

  摘要：

  Inhibition of GSK-3 beta has been well documented to account for the behavioral actions of the mood stabilizer lithium in various animal models of mood disorders. Recent studies have showed that genetic or pharmacological inhibition of GSK-3 beta resulted in anxiolytic-like and pro-social behavior. In our ongoing efforts to develop GSK-3 beta inhibitors for the treatment of mood disorders, SAR studies on maleimide-based compounds were undertaken. We present herein for the first time that some of these GSK-3 beta inhibitors, in particular analogues 1 and 9, were able to stimulate progesterone production in the MA-10 mouse tumor Leydig cell model of steroidogenesis without any significant toxicity. These two compounds were tested in the SmartCube behavioral assay and showed anxiolytic-like signatures following daily dose administration (50 mg/kg, ip) for 13 days. Taken together, these results support the hypothesis that GSK-3 beta inhibition could influence neuroactive steroid production thereby mediating the modulation of anxiety-like behavior in vivo.

  DOI：

  10.1021/jm400511s

文献信息

• [EN] SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE<br/>[FR] INHIBITEURS SÉLECTIFS DE MUTANTS CLINIQUEMENT IMPORTANTS DE LA TYROSINE KINASE DE L'EGFR
  申请人：CS PHARMATECH LTD

  公开号：WO2019010295A1

  公开（公告）日：2019-01-10

  The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof, or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof, and methods and compositions for treating or ameliorating abnormal cell proliferative disorders, such as cancer, wherein A, R2, R3, R10, E1, E2, E3, Y, and Z are as defined herein.

  本发明提供了式（I）的化合物或其亚类结构或种属，或其药学上可接受的盐、酯、溶剂化合物和/或前药，以及用于治疗或改善异常细胞增殖性疾病，如癌症的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。
• [EN] ISOTOPICALLY LABELED BIARYL UREA COMPOUNDS<br/>[FR] COMPOSÉS BIARYL URÉES, MARQUÉS DE FAÇON ISOTOPIQUE
  申请人：MERCK SHARP & DOHME

  公开号：WO2013181075A1

  公开（公告）日：2013-12-05

  The present invention is directed to isotopically labeled biaryl urea compounds which possess high affinity to neurofibrillary tangles (NFTs), and thus are useful to determine the amount and distribution of NFTs in brain. The isotopically labeled biaryl urea compounds may also be useful as PET tracers and in competition assays to identify other compounds that may serve as PET tracers.

  本发明涉及同位素标记的双芳基脲化合物，其具有高亲和力与神经纤维缠结体（NFTs）结合，因此可用于确定大脑中NFTs的数量和分布。同位素标记的双芳基脲化合物也可用作PET示踪剂，并用于竞争试验以鉴定其他可能用作PET示踪剂的化合物。
• Isotopically Labeled Biaryl Urea Compounds
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20150336948A1

  公开（公告）日：2015-11-26

  The present invention is directed to isotopically labeled biaryl urea compounds which possess high affinity to neurofibrillary tangles (NFTs), and thus are useful to determine the amount and distribution of NFTs in brain. The isotopically labeled biaryl urea compounds may also be useful as PET tracers and in competition assays to identify other compounds that may serve as PET tracers.

  本发明涉及同位素标记的双芳基脲化合物，具有高亲和力与神经纤维缠结体（NFTs）结合，因此可用于确定大脑中NFTs的数量和分布。同位素标记的双芳基脲化合物也可用作PET示踪剂和竞争测定中用于识别其他可能作为PET示踪剂的化合物。
• PPAR ACTIVE COMPOUNDS
  申请人：PLEXXIKON INC.

  公开号：EP1648867B1

  公开（公告）日：2013-09-04
• ISOTOPICALLY LABELED BIARYL UREA COMPOUNDS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2855477A1

  公开（公告）日：2015-04-08