1,3-dimethyl-7-methoxy-9H-β-carboline | 35596-09-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1,3-dimethyl-7-methoxy-9H-β-carboline
• 英文别名: 1-methyl-3-methyl-7-methoxy-9H-β-carboline；7-methoxy-1,3-dimethyl-9H-pyrido[3,4-b]indole；3-methylharmine；4-Methyl-harmin；7-methoxy-1,3-dimethyl-9H-β-carboline
• CAS: 35596-09-9
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: GXNDURPJXSLEMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl α-(hydroxyimino)-β-(6-methoxyindol-3-yl)propanoate 在 三乙基硅烷 、 lithium aluminium tetrahydride 、 sulfur 、 溶剂黄146 、 三氟乙酸 、 palladium dichloride 、 锌 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 35.0h， 生成 1,3-dimethyl-7-methoxy-9H-β-carboline
  参考文献：
  名称：

  WO2019183245A5

  摘要：

  公开号：

  WO2019183245A5

文献信息

• β-Carbolines: synthesis of harmane, harmine alkaloids and their structural analogs by thermolysis of 4-aryl-3-azidopyridines and investigation of their optical properties
  作者：Vladislav Yu. Shuvalov、Valeriya А. Elisheva、Anastasiya S. Belousova、Evgenii V. Arshinov、Larisa V. Glyzdinskaya、Marina А. Vorontsova、Sergei А. Chernenko、Aleksander S. Fisyuk、Galina P. Sagitullina

  DOI：10.1007/s10593-020-02625-4

  日期：2020.1

  their fluorescent properties in the study of their interaction with DNA and other biological targets, as well as with drug delivery vehicles. A new general method for the synthesis of harmane, harmine, and their structural analogs by thermolysis of substituted 4-aryl-3-azidopyridines was developed, and their optical properties were studied.

  对β-咔啉的兴趣是由这些化合物的生物活性以及在研究其与DNA和其他生物靶标以及与药物递送载体的相互作用中使用荧光性质引起的。提出了一种通过热取代取代的4-芳基-3-叠氮基吡啶合成海藻烷，氨苄及其结构类似物的新方法，并对其光学性质进行了研究。
• ORGANIC ELECTROLUMINESCENCE DEVICE AND ORGANOMETALLIC COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE
  申请人：Samsung Display Co., Ltd.

  公开号：US20210288270A1

  公开（公告）日：2021-09-16

  An organic electroluminescence device of an embodiment includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer includes an organometallic compound represented by Formula 1, and may show high emission efficiency properties.

  一种有机电致发光器件的实施例，包括第一电极、设置在第一电极上的第二电极以及设置在第一电极和第二电极之间的发射层，其中该发射层包括由式子1表示的有机金属化合物，可能表现出高发射效率的特性。
• WO2019183245A5
  申请人：——

  公开号：WO2019183245A5

  公开（公告）日：2022-03-25
• KINASE INHIBITOR COMPOUNDS AND COMPOSITIONS AND METHODS OF USE
  申请人：Icahn School of Medicine at Mount Sinai

  公开号：US20210094950A1

  公开（公告）日：2021-04-01

  Described herein are compounds having the following structure: formula (I) or a stereoisomer, pharmaceutically acceptable salt, oxide, or solvate thereof. Also disclosed are compositions containing the compounds, methods of inhibiting activity of DYRK1 A in a cell, methods of increasing cell proliferation in a population of pancreatic beta cells, methods of treating a subject for a condition associated with insufficient insulin secretion, and methods of treating a subject for a neurological disorder.
• Development of Kinase-Selective, Harmine-Based DYRK1A Inhibitors that Induce Pancreatic Human β-Cell Proliferation
  作者：Kunal Kumar、Peng Wang、Roberto Sanchez、Ethan A Swartz、Andrew F. Stewart、Robert J. DeVita

  DOI：10.1021/acs.jmedchem.8b00658

  日期：2018.9.13

  DYRK1A has been implicated as an important drug target in various therapeutic areas, including neurological disorders and oncology. DYRK1A has more recently been shown to be involved in pathways regulating human beta-cell proliferation, thus making it a potential therapeutic target for both Type 1 and Type 2 diabetes. Our group, using a high-throughput phenotypic screen, identified harmine that is able to induce beta-cell proliferation both in vitro and in vivo. Since harmine has suboptimal kinase selectivity, we sought to expand structure-activity relationships for harmine's DYRK1A activity, to enhance selectivity, while retaining human beta-cell proliferation capability. We carried out the optimization of the 1-position of harmine and synthesized 15 harmine analogues. Six compounds showed excellent DYRK1A inhibition with IC50 in the range of 49.5-264 nM. Two compounds, 2-2 and 2-8, exhibited excellent human beta-cell proliferation at doses of 3-30 mu M, and compound 2-2 showed improved kinase selectivity as compared to harmine.