4, 11-dibromoschizandrin | 71252-73-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 4, 11-dibromoschizandrin
• 英文别名: dibromoschizandrin；5,12-Dibromo-schizandrin；(9S,10S)-6,13-dibromo-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(12),2(7),3,5,13,15-hexaen-9-ol
• CAS: 71252-73-8
• 化学式: C₂₄H₃₀Br₂O₇
• 分子量: 590.306
• InChiKey: KMTKKULOWMDTND-BUBHHJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 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：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4, 11-dibromoschizandrin 、 sodium methylate 在 copper(II) choride dihydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-bromo-11-methoxylschizandrin
  参考文献：
  名称：

  二苯并环辛二烯木脂素衍生物的合成及其保肝活性

  摘要：

  合成了五味子素()、五味子素B()和五味子酚()的卤代和氧化衍生物(-、'-'、-、'-'、-、'和'-')。初步评估了这些二苯并环辛二烯木脂素类似物对 CCl 引起的损伤的保肝作用。大多数类似物比阳性对照联苯二甲酸酯（DDB）表现出更高的保护作用。在这些活性类似物中，二氯五味子酚（）表现出最强的保护活性（细胞存活率超过98.0%）。

  DOI：

  10.1016/j.bmcl.2014.02.020
• 作为产物：
  描述：

  schizandrin 在 水 、 溴 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以10.7 mg的产率得到4, 11-dibromoschizandrin
  参考文献：
  名称：

  Inhibitors of cAMP Phosphodiesterase in Medicinal Plants. Part XVIII. Inhibitors of Adenosine 3',5'-Cyclic Monophosphate Phosphodiesterase from Schisandra chinensis and the Structure Activity Relationship of Lignans.

  摘要：

  研究了五味子中类似木脂素及其衍生物的结构活性关系。测试了这些化合物对环腺苷 3'，5'-单磷酸（cAMP）磷酸二酯酶的抑制作用。从这种植物中分离出了一种抑制剂--正二氢愈创木脂酸（13），因此我们使用分子力学方法讨论了这种化合物及其衍生物--正二氢愈创木脂酸四甲基醚，包括使用 MM2PP 程序进行三维建模和结构最小化。结果发现，正氢愈创木脂酸四甲醚和罂粟碱（30）（阳性对照）的结构具有相似的低能构象。这一事实表明，这些化合物抑制 cAMP 磷酸二酯酶的机制相似。

  DOI：

  10.1248/cpb.40.1191

文献信息

• 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。
• The constituents of Schizandra chinensis Baill. I. Isolation and structure determination of five new lignans, gomisin A, B, C, F and G, and the absolute structure of schizandrin.
  作者：YUKINOBU IKEYA、HEIHACHIRO TAGUCHI、ITIRO YOSIOKA、HIROSHI KOBAYASHI

  DOI：10.1248/cpb.27.1383

  日期：——

  Five new dibenzocyclooctadiene lignans, named gomisin A (2), B (3), C (4), F (5) and G (6), were isolated from the petroleum ether extract of fruits of Schizandra chinensis BAILL. (Schizandraceae) and their absolute structures were elucidated by chemical and spectral techniques. The absolute structure of schizandrin (1), the plane structure of which had already been elucidated by Kochetkov et al., was also elucidated on the basis of spectroscopic results.

  从五味子果实石油醚提取物中分离得到 5 种新的二苯并环辛二烯木脂素，分别命名为 gomisin A (2)、B (3)、C (4)、F (5) 和 G (6)。通过化学和光谱技术阐明了五味子科（Schizandraceae）及其绝对结构。 Kochetkov等人已经阐明了五味子素(1)的平面结构，并且根据光谱结果也阐明了五味子素(1)的绝对结构。
• Anti-aids agents—XXVI. Structure-activity correlations of Gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues
  作者：Dao-Feng Chen、Shun-Xiang Zhang、Lan Xie、Jing-Xi Xie、Ke Chen、Yoshiki Kashiwada、Bing-Nan Zhou、Pei Wang、L.Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1016/s0968-0896(97)00118-1

  日期：1997.8

  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.
• Synthesis and the hepatoprotective activity of dibenzocyclooctadiene lignan derivatives
  作者：Tao He、Qing-Yao Wang、Jing-Zhen Shi、Tian-Yun Fan、Chen Yan、Lie-Jun Huang、Sheng Liu、Xiao-Jiang Hao、Shu-Zhen Mu

  DOI：10.1016/j.bmcl.2014.02.020

  日期：2014.4

  The halogenated and oxidized derivatives (–, ′–′, –, ′–′, –, ′ and ′–′) of schizandrin (), schizandrin B () and schisanhenol () were synthesized. The hepatoprotective effects of these dibenzocyclooctadiene lignan analogues against CCl-induced injury were preliminarily evaluated. Most of the analogues exhibited higher protective effects than the positive control biphenyldicarboxylate (DDB). Among these

  合成了五味子素()、五味子素B()和五味子酚()的卤代和氧化衍生物(-、'-'、-、'-'、-、'和'-')。初步评估了这些二苯并环辛二烯木脂素类似物对 CCl 引起的损伤的保肝作用。大多数类似物比阳性对照联苯二甲酸酯（DDB）表现出更高的保护作用。在这些活性类似物中，二氯五味子酚（）表现出最强的保护活性（细胞存活率超过98.0%）。
• Inhibitors of cAMP Phosphodiesterase in Medicinal Plants. Part XVIII. Inhibitors of Adenosine 3',5'-Cyclic Monophosphate Phosphodiesterase from Schisandra chinensis and the Structure Activity Relationship of Lignans.
  作者：Heigo SAKURAI、Tamotsu NIKAIDO、Taichi OHMOTO、Yukinobu IKEYA、Hiroshi MITSUHASHI

  DOI：10.1248/cpb.40.1191

  日期：——

  The structure activity relationship was studied in analogous lignans from Schisandra chinensis and their derivatives. These compounds were tested for cyclic adenosine 3', 5'-monophosphate (cAMP) phosphodiesterase inhibition. An inhibitor, nordihydroguaiaretic acid (13), was isolated from this plant, so we discussed this compound and a derivative, nordihydroguaiaretic acid tetramethyl ether, using molecular mechanics involving three-dimensional modeling and minimization of the structure using the MM2PP program. As a result, it was found that the structure of nordihydroguaiaretic acid tetrametyl ether and papaverine (30) (positive control) shared a similar low energy conformation. This fact suggested that these compounds inhibited cAMP phosphodiesterase by a similar mechanism.

  研究了五味子中类似木脂素及其衍生物的结构活性关系。测试了这些化合物对环腺苷 3'，5'-单磷酸（cAMP）磷酸二酯酶的抑制作用。从这种植物中分离出了一种抑制剂--正二氢愈创木脂酸（13），因此我们使用分子力学方法讨论了这种化合物及其衍生物--正二氢愈创木脂酸四甲基醚，包括使用 MM2PP 程序进行三维建模和结构最小化。结果发现，正氢愈创木脂酸四甲醚和罂粟碱（30）（阳性对照）的结构具有相似的低能构象。这一事实表明，这些化合物抑制 cAMP 磷酸二酯酶的机制相似。