schisandrin A | 156769-17-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: schisandrin A
• 英文别名: (+)-Deoxyschisandrin；(9R,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^2,7]hexadeca-1(16),2,4,6,12,14-hexaen-3-ol；cis-5,6,7,8-tetrahydro-1,2,3,10,11,12-hexamethoxy-6,7-dimethyldibenzo[a,c]cyclooctene；(+/-)-deoxyschizandrin；(+) deoxyschiszandrin；(9S,10R)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaene
• CAS: 156769-17-4
• 化学式: C₂₄H₃₂O₆
• 分子量: 416.514
• InChiKey: JEJFTTRHGBKKEI-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  schisandrin A 在 溴 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以84%的产率得到(6R,7S)-4,9-Dibromo-1,2,3,10,11,12-hexamethoxy-6,7-dimethyl-5,6,7,8-tetrahydro-dibenzo[a,c]cyclooctene
  参考文献：
  名称：

  Anti-aids agents—XXVI. Structure-activity correlations of Gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues

  摘要：

  Bioactivity-directed fractionation of an ethanolic extract of the stems of Kadsura interior led to the isolation and identification of 12 known lignans (1-12). Seven of these compounds (1, 6, 8-12) were active as anti-HIV agents. Gomisin-G (11) exhibited the most potent anti-HIV activity with EC50 and therapeutic index (TI) Values of 0.006 mu g/mL and 300, respectively. Schisantherin-D (6), kadsuranin (8), and schisandrin-C (10) showed good activity with EC50 values of 0.5, 0.8, and 1.2 mu g/mL, and TI values of 110, 56, and 33.3, respectively. Ten related synthetic biphenyl compounds, five variously substituted bismethylenedioxy, dimethoxy, and dimethoxycarbonyl isomers (18-22) and five brominated derivatives (23-27) also were evaluated for inhibitory activity against HIV-1 replication in acutely infected H9 cells. The total syntheses of two new isomers (21 and 22) are reported for the first time. The anti-HIV data indicated that the relative position and types of substituents on the phenolic hydroxy groups of either the natural lignans or the synthetic biphenyl compounds rather than the numbers of bromine(s) on the aromatic rings art of primary importance. In the cyclooctane ring of the natural lignans, the position and substitution of hydroxy groups are also important to enhanced anti-HIV activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00118-1
• 作为产物：
  描述：

  (-)-schizandrin 在 platinum(IV) oxide 氢气 、 三氯氧磷 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 2.5h， 生成 schisandrin A
  参考文献：
  名称：

  五味子木脂素

  摘要：

  摘要 从五味子果实中分离得到一种新的二苯并环辛二烯木脂素异五味子素。基于光谱分析和五味子素和(+)-脱氧五味子素的化学相关性阐明了结构。在使用大鼠的实验中，五味子及其衍生物，包括异五味子，显示出对应激性胃溃疡 (po) 的抑制作用。

  DOI：

  10.1016/0031-9422(88)83143-1

文献信息

• Synthesis of (±)-deoxyschizandrin
  作者：Tesfaye Biftu、Braja G. Hazra、Robert Stevenson

  DOI：10.1039/p19790002276

  日期：——

  1,4-Diarylbutanes undergo intramolecular oxidation with vanadium oxytrifluoride to yield dibenzo[a, c]cyclooctenes. Two short synthetic routes to the lignan, (±)-deoxyschizandrin have been developed from 3,4,5-trimethoxypropiophenone.

  1,4-二芳基丁烷与三氟氧化钒进行分子内氧化，生成二苯并[ a，c ]环辛烯。由3,4,5-三甲氧基苯乙酮已开发出两种合成木脂素的短合成路线，即（±）-脱氧五味子素。
• Synthesis of the lignan (±)-deoxyschizandrin
  作者：Tesfaye Biftu、Braja G. Hazra、Robert Stevenson

  DOI：10.1039/c39780000491

  日期：——

  A short synthesis of the bisbenzocyclo-octadiene lignan, (±)-deoxyschizandrin (1), based upon an intramolecular oxidation of 1,4-diarylbutane is described.

  描述了基于1,4-二芳基丁烷的分子内氧化的双苯并环-辛二烯木脂素（（±）-脱氧五味子素（1））的简短合成。
• Ruthenium dioxide in fluoro acid medium: I. A new agent in the biaryl oxidative coupling. Application to the synthesis of non phenolic bisbenzocyclooctadiene lignan lactones.
  作者：Y Landais、J.-P Robin、A Lebrun

  DOI：10.1016/s0040-4020(01)80904-2

  日期：——

  very efficient agent for the oxidative coupling of non phenolic lignans and their derivatives, and this method was applied to the total synthesis of (+/-)-neoisostegane 2a and (+/-)-steganolide A 2b. This procedure was also used to obtain the first stereospecific synthesis of a cis-bisbenzocyclooctadiene lactone, the (+/-)-deoxyschizandrin 17, of which, was afforded by a short reduction sequence.

  氟酸介质中的二水合钌（IV）被发现是非酚类木脂素及其衍生物氧化偶联的非常有效的试剂，该方法被用于（+/-）-neosoostegane 2a和（ +/-）-硬脂酸内酯A 2b。该方法还用于获得顺式-双苯并环辛二烯内酯的第一个立体有择合成，其（+/-）-脱氧五味子甲酸酯17是通过短还原序列提供的。
• A Concise Total Synthesis of Deoxyschizandrin and Exploration of Its Antiproliferative Effects and those of Structurally Related Derivatives
  作者：Shaojun Zheng、Sarah J. Aves、Luca Laraia、Warren R. J. D. Galloway、Kurt G. Pike、Wenjun Wu、David R. Spring

  DOI：10.1002/chem.201103530

  日期：2012.3.12

  have a wide range of biological activities. In recent years the therapeutic potential of this compound against cancers has attracted significant interest. Herein we describe a concise de novo total synthesis of deoxyschizandrin based around a double organocuprate oxidation strategy. In addition, we present the results of biological studies exploring the ability of deoxyschizandrin and synthetic precursors

  天然产物脱氧五味子素已被证明具有广泛的生物活性。近年来，这种化合物对癌症的治疗潜力引起了人们极大的兴趣。在此，我们描述了基于双有机铜酸盐氧化策略的脱氧五味子素的简洁从头全合成。此外，我们还介绍了探索脱氧五味子素和缺乏中等环联芳基单元的合成前体抑制人类癌细胞系增殖能力的生物学研究结果。这些研究导致鉴定出一种具有体外抗癌活性的结构新颖的药物。
• 联苯环辛二烯类木脂素及其卤代衍生物选择 性脱甲氧基方法
  申请人：贵州省中国科学院天然产物化学重点实验室

  公开号：CN107652168B

  公开（公告）日：2020-12-15

  本发明公开了一种联苯环辛二烯类木脂素及其卤代衍生物选择性脱甲氧基方法，是按照如下路线进行：以化合物(I)为原料，溶解于溶剂中，加入金属钠，在25℃～60℃反应，得到化合物(II)。本发明提供的一种联苯环辛二烯类木脂素及其卤代衍生物选择性脱甲氧基方法，反应体系易得，操作方法简单。本发明方法中采用金属钠/醇反应体系，在脱卤的同时可以选择性的脱甲氧基。采用本发明方法所得产物选择性好，产物纯度高，反应产率高。本发明方法具有反应条件温和，反应时间短，所需试剂便宜易得，生产成本低，可以大规模推广的特点。