6-溴-7-(甲基氨基)异喹啉-5,8-二酮 | 662167-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 6-溴-7-(甲基氨基)异喹啉-5,8-二酮
• 英文名称: Caulibugulone B
• 英文别名: 6-bromo-7-(methylamino)isoquinoline-5,8-dione
• CAS: 662167-16-0
• 化学式: C₁₀H₇BrN₂O₂
• 分子量: 267.082
• InChiKey: YZQJGPPACTZUKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-(甲基氨基)异喹啉-5,8-二酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以74%的产率得到6-溴-7-(甲基氨基)异喹啉-5,8-二酮
  参考文献：
  名称：

  Synthesis and biological evaluation of caulibugulones A–E

  摘要：

  海洋珊瑚虫代谢物caulibugulone A–E是从一种易得的异喹啉二酮中制备的。这些天然产物被发现是双特异性磷酸酶Cdc25B的有效且选择性的抑制剂。

  DOI：

  10.1039/b408184f

文献信息

• Exploitation of a Tuned Oxidation with <i>N</i>-Haloimides in the Synthesis of Caulibugulones A–D
  作者：Fabrício F. Naciuk、Julio C. Milan、Almir Andreão、Paulo C. M. L. Miranda

  DOI：10.1021/jo302772t

  日期：2013.5.17

  Marine alkaloids caulibugulones A-D were synthesized in six steps starting from the readily available 2,5-dimethoxybenzaldehyde. Pomeranz-Fritsch reaction of N-(2,S-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzenesulfonamide proceeded smoothly to give 5,8-dimethoxyisoquinoline, which was oxidized to isoquinolinadiones by a tunable oxidation reaction with N-haloimides. Therefore, NBS furnished direct conversion to the isoquinoline-5,8-dione; alternatively, N-haloimides of cyanuric acid provided both oxidation and halogenation generating 6,7-dihaloisoquinoline-5,8-diones. Aminolyses of these isoquinolinediones with methylamine or ethanolamine produced the isoquinolinedione alkaloids caulibugulones A-D in 24-57% overall yield.
• Total synthesis of the marine cytotoxic caulibugulones A–D
  作者：David Alagille、Ronald M Baldwin、Gilles D Tamagnan

  DOI：10.1016/j.tetlet.2004.06.007

  日期：2004.8

  We report the first total synthesis of the cytotoxic marine alkaloids caulibugulone A-D. This synthesis confirmed the assigned structures and provided sufficient material for further biological testing. (C) 2004 Elsevier Ltd. All rights reserved.
• Caulibugulones A−F, Novel Cytotoxic Isoquinoline Quinones and Iminoquinones from the Marine Bryozoan <i>Caulibugula intermis</i>
  作者：Dennis J. Milanowski、Kirk R. Gustafson、James A. Kelley、James B. McMahon

  DOI：10.1021/np030378l

  日期：2004.1.1

  An extract of the marine bryozoan Caulibugula intermis, collected in the Indo-Pacific off Palau, produced a distinct pattern of differential cytotoxicity in the National Cancer Institute's 60 cell line antitumor screen. Bioactivity-directed fractionation of the extract provided six new compounds, caulibugulones A-F (1-6). The structures of these novel metabolites were determined by spectrochemical analyses including LC-MS, HRFABMS, 1-D and 2-D NMR experiments, and by comparison with related compounds. The structures of compounds 2 and 3 were confirmed by chemical interconversion. The isolated compounds exhibited IC50's of 0.03-1.67 mug/mL against murine tumor cells in an in vitro cytotoxicity assay.
• Synthesis and biological evaluation of caulibugulones A–E
  作者：Peter Wipf、Beomjun Joo、Theresa Nguyen、John S. Lazo

  DOI：10.1039/b408184f

  日期：——

  The marine bryozoan metabolites caulibugulone A–E were prepared from a readily available isoquinoline dione. These natural products were found to be potent and selective inhibitors of the dual specificity phosphatase Cdc25B.

  海洋珊瑚虫代谢物caulibugulone A–E是从一种易得的异喹啉二酮中制备的。这些天然产物被发现是双特异性磷酸酶Cdc25B的有效且选择性的抑制剂。

表征谱图