Caulibugulone D

• 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
• 英文名称: Caulibugulone D
• 英文别名: 7-(2-hydroxyethylamino)isoquinoline-5,8-dione
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: JPUNXFPVVKDHNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,8-dimethoxyisoquinoline 在 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 硫酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 68.0h， 生成 Caulibugulone D
  参考文献：
  名称：

  Exploitation of a Tuned Oxidation with N-Haloimides in the Synthesis of Caulibugulones A–D

  摘要：

  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.

  DOI：

  10.1021/jo302772t

文献信息

• 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。
• Total synthesis of the marine alkaloids Caulibugulones A and D
  作者：K.S. Prakash、Rajagopal Nagarajan

  DOI：10.1016/j.tet.2014.12.059

  日期：2015.2

  Total synthesis of the marine cytotoxic alkaloids Caulibugulones A and D is accomplished in three steps with an overall yield of 60-62% from easily accessible starting materials. The key features include isoquinoline-5,8-diol core construction by ammonia mediated iminoannulation of 2-ethyny1-3,6-dihydroxybenzaldehyde, and subsequent in situ oxidation followed by oxidative amination. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.
• 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.

表征谱图