dibromogomisin A | 58546-57-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: dibromogomisin A
• 英文别名: 5,12-Dibromo-gomisin A；(9S,10S)-6,13-dibromo-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol
• CAS: 58546-57-9
• 化学式: C₂₃H₂₆Br₂O₇
• 分子量: 574.263
• InChiKey: VLEHHPXKBWXPED-VCGICTTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  gomisin A 在 水 、 溴 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以12.3 mg的产率得到dibromogomisin A
  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

• 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。
• 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.