2,3,10,11-tetramethoxyberbinium iodide | 10211-02-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 2,3,10,11-tetramethoxyberbinium iodide
• 英文别名: pseudopalmatine iodide；2,3,10,11-tetramethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium; iodide；2,3,10,11-Tetramethoxy-5,6-dihydro-isochino[3,2-a]isochinolinylium; Jodid；2,3,10,11-Tetramethoxy-protoberberiniumiodid；5,6-Dihydro-2,3,10,11-tetramethoxydibenzo(a,g)quinolizinium iodide；2,3,10,11-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium;iodide
• CAS: 10211-02-6
• 化学式: C₂₁H₂₂NO₄*I
• 分子量: 479.314
• InChiKey: OUWHTAHYTZRWQZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 2,3,10,11-tetramethoxyberbinium iodide 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  On the diffusion of probabilistic investment appraisal and decision-making procedures in the UK’s upstream oil and gas industry

  摘要：

  A critical activity for companies involved in the upstream oil and gas industry is deciding whether or not to invest in developing hydrocarbon prospects. Decisions are characterised by combinations of uncertainty and incomplete information assembled by professionals with different. but highly complementary areas of expertise. This paper presents evidence of variation among companies in the industry in the extent to which formal appraisal and decision-making procedures are adopted, and, where adopted, in the manner of application. An explanation is set out in which the importance of senior managers' attitudes is tempered by limits to the adaptability of organisational routines, of which appraisal and decision-making processes are prominent. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0048-7333(01)00171-8
• 作为产物：
  描述：

  2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline 在 碘 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到2,3,10,11-tetramethoxyberbinium iodide
  参考文献：
  名称：

  Methoxy- and acetoxy-8-oxoberbines - 合成、抗肿瘤活性以及与 DNA 的相互作用

  摘要：

  大多数甲氧基-8H-二苯并[a,g]异喹啉-8-酮3a-h及其乙酰氧基衍生物6a-e是通过1-氧代-1,2,3,4-四氢异喹啉4a-c和邻苯二甲酸酐5a和b，醚裂解和乙酰化。使用 MDA-MB-231 乳腺肿瘤细胞测试了这些原小檗酮的体外细胞抑制活性以及与天然小牛胸腺 DNA 的相互作用。四甲氧基-8-oxoberbine 3f 在浓度为 10-5 摩尔时显示出 87% 的细胞增殖抑制作用；它的细胞抑制作用不依赖于嵌入 DNA。

  DOI：

  10.1002/ardp.2503240810

文献信息

• Hypotensive Methoxyisoquinolines
  作者：Gordon N. Walker

  DOI：10.1021/ja01644a042

  日期：1954.8
• A novel oxidation stage in the chemistry of protoberberine alkaloids. Synthesis of 7,8-dehydroberbines
  作者：Rafael Suau、M.Victoria Silva、Maria Valpuesta

  DOI：10.1016/s0040-4020(01)86534-0

  日期：1991.7

  1,2-substituted berbines, such as (-)-caseamine, (-)-caseadine and (-)-O-methylcaseadine, are partially oxidized by iodine to the 7,8-dehydroberbines, while the 2,3-substituted berbines are oxidized all the way to the protoberberinium salts. This different behaviour is interpreted in terms of the preferred cis or trans B/C quinolizidine conformation of the starting berbines.
• LC–NMR and LC–MS analysis of 2,3,10,11-oxygenated protoberberine metabolites in Corydalis cell cultures
  作者：Kinuko Iwasa、Ayako Kuribayashi、Makiko Sugiura、Masataka Moriyasu、Dong-Ung Lee、Wolfgang Wiegrebe

  DOI：10.1016/s0031-9422(03)00497-7

  日期：2003.12

  The metabolism of 2,3, 10,1 I-oxygenated protoberberine alkaloids was studied in cell cultures of Corydalis species. Without prior isolation, the structures of the metabolites were determined by LC-MS and LC-NMR analyses. Tetrahydropseudocoptisine alpha-N-metho salt, pseudoprotopine, and pseudomuramine were identified for the first time, and preliminary evidence for metabolic pathways to the formation of these alkaloids were obtained. (C) 2003 Elsevier Ltd. All rights reserved.