7-(甲基氨基)异喹啉-5,8-二酮 | 662167-15-9

• 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: 7-(甲基氨基)异喹啉-5,8-二酮
• 英文名称: caulibugulone A
• 英文别名: 7-(Methylamino)isoquinoline-5,8-dione
• CAS: 662167-15-9
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: PETJKYHAQBWMDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 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

• 作为反应物：
  描述：

  7-(甲基氨基)异喹啉-5,8-二酮 在 N-氯代丁二酰亚胺 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以82%的产率得到6-氯-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
• 作为产物：
  描述：

  N-(2,5-二甲氧基苄基)-N-(2,2-二甲氧基乙基)-4-甲基苯磺酰胺 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 硫酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 叔丁醇 为溶剂， 反应 75.5h， 生成 7-(甲基氨基)异喹啉-5,8-二酮
  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

• [EN] IN-FLOW PHOTOOXYGENATION OF AMINOTHIENOPYRIDINONES GENERATES NOVEL PTP4A3 PHOSPHATASE INHIBITORS<br/>[FR] PHOTOOXYGÉNATION EN FLUX D'AMINOTHIENOPYRIDINONES GÉNÉRANT DE NOUVEAUX INHIBITEURS DE PHOSPHATASE PTP4A3
  申请人：UNIV VIRGINIA PATENT FOUNDATION

  公开号：WO2020102245A1

  公开（公告）日：2020-05-22

  The disclosure provides compounds that inhibit protein tyrosine phosphatase, such as protein tyrosine phosphatase 4A3 (PTP4A3). The disclosure also provides pharmaceutical compositions, uses, and methods of using the compounds, such as in the treatment of cancers. (I), wherein X is O or NH.

  该披露提供了抑制蛋白酪氨酸磷酸酶的化合物，例如蛋白酪氨酸磷酸酶4A3（PTP4A3）。该披露还提供了药物组合物、用途以及使用这些化合物的方法，例如在癌症治疗中的应用。（I），其中X为O或NH。
• 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.
• 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.
• IN-FLOW PHOTOOXYGENATION OF AMINOTHIENOPYRIDINONES GENERATES NOVEL PTP4A3 PHOSPHATASE INHIBITORS
  申请人：University of Virginia Patent Foundation

  公开号：EP3880200A2

  公开（公告）日：2021-09-22