ancistrocladine | 32221-59-3

• 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: ancistrocladine
• 英文别名: hamatine；Ancistrocladin；Hamatin；(1S,3S)-5-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
• CAS: 32221-59-3；36209-88-8；56688-90-5；57030-01-0
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: XUFOYASAFNKRRE-GJZGRUSLSA-N

物化性质

• 沸点：
  565.3±50.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ancistrocladine 在 sodium tetrahydroborate 、 thallium (I) ethoxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-methyl-ancistrocladine triflic ester
  参考文献：
  名称：

  Dioncophylline C from the roots of Triphyophyllum peltatum, the first 5,1′-coupled dioncophyllaceae alkaloid

  摘要：

  A new naphthylisoquinoline alkaloid, named dioncophylline C, was isolated from the roots of Triphyophyllum peltatum. Its complete stereostructure was established by spectroscopic, chiroptical, and chemical methods. Dioncophylline C is the first 5,1'-linked Dioncophyllaceae alkaloid; this coupling type has hitherto been found only for Ancistrocladaceae alkaloids, yet with a different stereochemistry and a higher oxygenation degree.

  DOI：

  10.1016/s0031-9422(00)97576-9
• 作为产物：
  描述：

  1-溴-2-(溴甲基)-4,5-二甲氧基萘 在 palladium on activated charcoal 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 lithium aluminium tetrahydride 、 1,2-二溴四氯乙烷 、 N,N-二甲基乙酰胺 、 polym. PPh₃ 、 氢气 、 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 ancistrocladine
  参考文献：
  名称：

  Bringmann, Gerhard; Jansen, Johannes R.; Rink, Heinz-Peter, Angewandte Chemie, 1986, vol. 98, # 10, p. 917 - 919

  摘要：

  DOI：

文献信息

• Synthetic approaches to the naphthyl-isoquinoline alkaloids. Part 2. The total synthesis of (–)-O-methylancistrocladine and (+)-O-methylhamatine and their enantiomers
  作者：Mark A. Rizzacasa、Melvyn V. Sargent

  DOI：10.1039/p19910000845

  日期：——

  of the naphthyl-isoquinoline alkaloids (–)-O-methytancistrocladine 39 is described; the synthetic method also provides routes to the atropisomer (+)-O-methylhamatine 43 and the enantiomers of these alkaloids. The asymmetric construction of the biaryl linkage involved the reaction of the Grignard reagent derived from 2-(2-bromo-3,5-dimethoxyphenyl)-1,3-dioxane 7 with (+)-(4S,5S)-4-(methoxymethyl)-5-phenyl-2-(1

  描述了萘基-异喹啉生物碱（-）- O-甲基-tantantrotrod的非对称全合成；39。该合成方法还提供了到达阻转异构体（+）- O-甲基ham丁啶43和这些生物碱的对映异构体的途径。联芳基键的不对称结构涉及衍生自2-（2-溴-3,5-二甲氧基苯基）-1,3-二恶烷7的格利雅试剂与（+）-（4 S，5 S）-4的反应-（甲氧基甲基）-5-苯基-2-（1,4,5-三甲氧基-2-萘基）-4,5-二氢恶唑5。
• 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。
• Absolute stereochemistry of ancistrocladine and ancistrocladinine
  作者：Tuticorin R. Govindachari、Kuppuswamy Nagarajan、Papagudi C. Parthasarathy、Tuticorin G. Rajagopalan、Haridutt K. Desai、Gopinath Kartha、Sow-mei Lai Chen、Koji Nakanishi

  DOI：10.1039/p19740001413

  日期：——

  Evidence for the absolute stereochemistry of ancistrocladine [(1S,3S)-5(R)-(4,5-dimethoxy-2-methyl-1-naphthyl)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethylisoquinolin-6-ol](1) and ancistrocladinine[(3S)-5(R)-(4,5-dimethoxy-2-methyl-1-naphthyl)-3,4-dihydro-8-methoxy-1,3-dimethylisoquinolin-6-ol](2), based on a study of n.m.r., X-ray, c.d., and chemical data, is presented.

  Ancistrocladine [（1 S，3 S）-5（R）-（4,5-二甲氧基-2-甲基-1-甲基）-1,2,3,4-四氢-8-甲氧基的绝对立体化学的证据-1,3-二甲基异喹啉-6-ol]（1）和顺氯丁宁[（3 S）-5（R）-（4,5-二甲氧基-2-甲基-1-甲基-1-萘基）-3,4-二氢-8提出了基于对NMR，X射线，CD和化学数据的研究的-甲氧基-1,3-二甲基异喹啉-6-醇]（2）。
• Jozimine B, a Constitutionally Unsymmetric, Antiplasmodial ‘Dimer’ of the Naphthylisoquinoline Alkaloid Ancistrocladine
  作者：Gerhard Bringmann、Wael Saeb、Jürgen Kraus、Reto Brun、Guido François

  DOI：10.1016/s0040-4020(00)00272-6

  日期：2000.5

  The first synthesis of a constitutionally unsymmetric bis-naphthylisoquinoline, the unnatural ‘dimer’ of the Ancistrocladus alkaloid ancistrocladine, jozimine B, is described. The constitution and the configuration at the new, central biaryl axis were established through extensive NMR investigations and quantum chemical CD calculations. Compared with ancistrocladine, its only weakly antiplasmodial

  描述了结构不对称的双萘基异喹啉的首次合成，这是Ancistrocladus生物碱anthtrocladine，jozimine B的非天然“二聚体” 。通过广泛的NMR研究和量子化学CD计算，确定了新的中心联芳基轴的结构和构型。与其唯一的抗疟原虫单体弱前体Ancistrocladine相比，Jozimine B表现出明显增强的抗疟疾活性。
• Monomeric and dimeric naphtylisoquinoline alkaloids and synthesis methods thereof
  申请人：THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, Department of Health and Human Services

  公开号：EP1325915A1

  公开（公告）日：2003-07-09

  The present invention provides methods of preparing monomeric naphthylisoquinoline alkaloids, including the antiparasitic korupensamines and related compounds, as well as non-korupensamines and other monomeric naphthylisoquinoline alkaloids. The present invention also provides methods of preparing dimeric naphthylisoquinoline alkaloids by coupling together two monomeric naphthylisoquinoline alkaloids, each of which may be the same or different, and one, both, or neither of which may possess a C-8' to C-5 naphthalene/isoquinoline linkage, to form homodimers or heterodimers, including the antiviral michellamines. The present invention further provides new, medically useful monomeric naphthylisoquinoline compounds and homodimeric and heterodimeric naphthylisoquinoline compounds and derivatives thereof.

  本发明提供了制备单体萘基异喹啉生物碱的方法，包括抗寄生虫的korupensamines和相关化合物，以及非korupensamines和其他单体萘基异喹啉生物碱。本发明还提供了通过将两种单体萘基异喹啉生物碱偶联在一起制备二聚体萘基异喹啉生物碱的方法，每种单体萘基异喹啉生物碱可以是相同的或不同的，其中一种、两种或两种都不具有 C-8' 至 C-5 萘/异喹啉连接，形成同二聚体或异二聚体，包括抗病毒的小檗胺。本发明进一步提供了新的、在医学上有用的单体萘异喹啉化合物和同源二聚体和异源二聚体萘异喹啉化合物及其衍生物。