1-acetyl-7-methoxy-9H-β-carboline | 62230-10-8

• 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-acetyl-7-methoxy-9H-β-carboline
• 英文别名: arenarine C；1-(7-Methoxy-9H-pyrido[3,4-b]indol-1-yl)ethan-1-one；1-(7-methoxy-9H-pyrido[3,4-b]indol-1-yl)ethanone
• CAS: 62230-10-8
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: SNGVLDNQSXBDPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-7-methoxy-9H-β-carboline 在 甲醇 、 sodium tetrahydroborate 作用下， 以49%的产率得到1-(1-hydroxyethyl)-7-methoxy-9H-β-carboline
  参考文献：
  名称：

  WO2019183245A5

  摘要：

  公开号：

  WO2019183245A5
• 作为产物：
  描述：

  3-(2-氨基乙基)-6-甲氧基吲哚 在 potassium permanganate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 1-acetyl-7-methoxy-9H-β-carboline
  参考文献：
  名称：

  Development of Kinase-Selective, Harmine-Based DYRK1A Inhibitors that Induce Pancreatic Human β-Cell Proliferation

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.8b00658

文献信息

• SMALL-MOLECULE INHIBITORS OF THE ANDROGEN RECEPTOR
  申请人：Diamond Marc

  公开号：US20080293766A1

  公开（公告）日：2008-11-27

  The present invention provides a method of inhibiting an androgen receptor by administering a compound of Formula I: or a compound of Formula II: wherein R 1 , R 2 , R 3 and R 8 are each independently hydrogen or C 1-6 alkyl. R 4 is absent or is hydrogen, C 1-6 alkyl or C 1-6 alkyl-OH. R 5 is hydrogen, C 1-6 alkyl or —NR 6 R 7 . R 6 and R 7 are each independently hydrogen or C 1-6 alkyl, or are combined with the nitrogen to which they are attached to form a heterocycloalkyl having from 5 to 7 ring members. L is a linker of C 1-6 alkylene, C 2-6 alkenylene, C 2-6 alkynylene or C 3-6 cycloalkylene. The compounds of Formula I include the salts, hydrates and prodrugs thereof. Each R 9 is H, C 1-6 alkyl, —OH or —O—C 1-6 alkyl. The compounds of Formulas I and II include the salts, hydrates and prodrugs thereof. By administering the compound of Formula I or II, the method inhibits the androgen receptor.

  本发明提供了通过给予式I的化合物或式II的化合物来抑制雄激素受体的方法：其中R1、R2、R3和R8分别独立地为氢或C1-6烷基。R4不存在或为氢、C1-6烷基或C1-6烷基-OH。R5为氢、C1-6烷基或-NR6R7。R6和R7分别独立地为氢或C1-6烷基，或与它们连接的氮原子结合形成具有5至7个环成员的杂环烷基。L为C1-6烷基、C2-6烯基、C2-6炔基或C3-6环烷基的连接剂。式I的化合物包括其盐、水合物和前药。每个R9为H、C1-6烷基、-OH或-O-C1-6烷基。式I和II的化合物包括其盐、水合物和前药。通过给予式I或II的化合物，该方法抑制雄激素受体。
• Wu, Feng-E; Koike, Kazuo; Nikaido, Tamotsu, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 7, p. 1808 - 1809
  作者：Wu, Feng-E、Koike, Kazuo、Nikaido, Tamotsu、Sakamoto, Yohko、Ohmoto, Taichi、Ikeda, Kejii

  DOI：——

  日期：——
• MARKING OF MATERIAL, MARKED MATERIAL AND PROCESS OF AUTHENTICATION OR DILUTION DETERMINATION
  申请人：Sicpa Holding SA

  公开号：EP2926119A1

  公开（公告）日：2015-10-07
• 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.
• US7696227B2
  申请人：——

  公开号：US7696227B2

  公开（公告）日：2010-04-13