6,7-dimethoxy-1-(3,4,5-trimethoxyphenyl)isoquinoline | 3161-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6,7-dimethoxy-1-(3,4,5-trimethoxyphenyl)isoquinoline
• CAS: 3161-13-5
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: YNIDGPXYNUWRKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(3',4'-dimethoxyphenethyl)-3,4,5-trimethoxybenzamide 在 钯 、 xylene 、 三氯氧磷 、 苯 作用下， 生成 6,7-dimethoxy-1-(3,4,5-trimethoxyphenyl)isoquinoline
  参考文献：
  名称：

  Slotta; Haberland, Angewandte Chemie, 1933, vol. 46, p. 766,770, 771

  摘要：

  DOI：

文献信息

• Cerium Chloride Catalyzed, 2-Iodoxybenzoic Acid Mediated Oxidative Dehydrogenation of Multiple Heterocycles at Room Temperature
  作者：Santanu Hati、Subhabrata Sen

  DOI：10.1002/ejoc.201601419

  日期：2017.3.3

  Catalytic cerium chloride was found to activate 2-iodoxybenzoic acid (IBX) for the oxidative dehydrogenation of tetrahydroisoquinolines, tetrahydro-β-carbolines, and thiazolidines to their dehydrogenated and aromatic forms at room temperature in moderate to excellent yields. The robustness of the protocol was demonstrated by scaling up the reactions to multigram quantities.

  发现催化氯化铈活化 2-碘氧基苯甲酸 (IBX)，用于在室温下将四氢异喹啉、四氢-β-咔啉和噻唑烷氧化脱氢为其脱氢和芳族形式，产率中等至极好。该协议的稳健性通过将反应放大到数克数量来证明。
• Isoquinoline-based biaryls as a robust scaffold for microtubule inhibitors
  作者：Yvonne Kraus、Carina Glas、Benedikt Melzer、Li Gao、Constanze Heise、Monique Preuße、Julia Ahlfeld、Franz Bracher、Oliver Thorn-Seshold

  DOI：10.1016/j.ejmech.2019.111865

  日期：2020.1

  We here report the discovery of isoquinoline-based biaryls as a new scaffold for colchicine domain tubulin inhibitors. Colchicinoid inhibitors offer highly desirable cytotoxic and vascular disrupting bioactivities, but their further development requires improving in vivo robustness and tolerability: properties that both depend on the scaffold structure employed. We have developed isoquinoline-based biaryls as a novel scaffold for high-potency tubulin inhibitors, with excellent robustness, druglikeness, and facile late-stage structural diversification, accessible through a tolerant synthetic route. We confirmed their bioactivity mechanism in vitro, developed soluble prodrugs, and established safe in vivo dosing in mice. By addressing several problems facing the current families of inhibitors, we expect that this new scaffold will find a range of in vivo applications towards translational use in cancer therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.
• DE614703
  申请人：——

  公开号：——

  公开（公告）日：——