jozimine C

• 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: jozimine C
• 英文别名: (1R,3R)-5-[5-hydroxy-6-[1-hydroxy-5-[(1R,3R)-8-hydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-8-methoxy-6-methylnaphthalen-2-yl]-4-methoxy-2-methylnaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
• 化学式: C₄₆H₄₈N₂O₆
• 分子量: 724.897
• InChiKey: JAFVZDVYFKJAAI-VEYUFSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  54
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  123
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  8-溴-4-甲氧基-5-(1-甲基乙氧基)-2-萘羧酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 sodium chlorite 、 lithium aluminium tetrahydride 、 甲酸 、 草酰氯 、 三正丁胺 、 1,2-二溴四氯乙烷 、 1,3-双(二苯基膦)丙烷 、 氨基磺酸 、 三氟化硼 、 氢气 、 sodium acetate 、 thallium (I) ethoxide 、 tetra-N-butylammonium tribromide 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 、 N,N-二甲基乙酰胺 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -40.0~100.0 ℃ 、500.0 kPa 条件下， 反应 99.25h， 生成 jozimine C
  参考文献：
  名称：

  First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C

  摘要：

  The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10301-5

文献信息

• Oxidative aryl coupling reactions: a biomimetic approach to configurationally unstable or axially chiral biaryl natural products and related bioactive compounds
  作者：Gerhard Bringmann、Stefan Tasler

  DOI：10.1016/s0040-4020(00)00940-6

  日期：2001.1

  products and related compounds in the fields of biphenyls, biscarbazoles and bisnaphthylisoquinolines. For sterically more hindered biaryls, which consequently show the phenomenon of axial chirality, the products were prepared in an atropisomerically pure form. Their absolute axial configurations were assigned mainly by experimental and computational CD investigations.

  酚和非酚氧化芳基偶联反应已成功用于联苯，双咔唑和双萘基异喹啉领域的各种天然产物和相关化合物的有效合成中。对于在空间上更受阻的联芳基，其因此表现出轴向手性现象，将产物制备为阻转异构纯形式。它们的绝对轴向构型主要通过实验和计算CD研究确定。
• First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C
  作者：Gerhard Bringmann、Jörg Holenz、Ralf Weirich、Martin Rübenacker、Christian Funke、Michael R. Boyd、Robert J. Gulakowski、Guido François

  DOI：10.1016/s0040-4020(97)10301-5

  日期：1998.1

  The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved.