Takinolide dimer | 1176188-49-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: Takinolide dimer
• 英文别名: (6R,12R)-6,12-bis(hydroxymethyl)-6,12-di(undecyl)-1,7-dioxacyclododecane-2,8-dione
• CAS: 1176188-49-0
• 化学式: C₃₄H₆₄O₆
• 分子量: 568.879
• InChiKey: OTCVHAIYZWVNGN-KKLWWLSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  40
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Takinolide dimer 在 盐酸 、 水 作用下， 反应 16.0h， 生成 (R)-5-hydroxy-5-(hydroxymethyl)hexadecanoic acid 、 (S)-5-Hydroxy-5-hydroxymethyl-hexadecanoic acid
  参考文献：
  名称：

  Structural and Synthetic Investigations of Tanikolide Dimer, a SIRT2 Selective Inhibitor, and Tanikolide seco-Acid from the Madagascar Marine Cyanobacterium Lyngbya majuscula

  摘要：

  Tanikolide seco-acid 2 and tanikolide dimer 3, the latter a novel and selective SIRT2 inhibitor, were isolated from the Madagascar marine cyanobacterium Lyngbya majuscula. The structure of 2, isolated as the pure R enantiomer, was elucidated by X-rayexperiment in conjunction with NMR and optical rotation data, whereas the depside molecular structure of 3 was initially thought to be a meso compound as established by NMR, MS, and chiral H PLC analyses. Subsequent total synthesis of the three tanikolide dimer stereoisomers 4, 5, and ent-5, followed by chiral GC-MS comparisons with the natural product, showed it to be exclusively the R,R-isomer 5. Tanikolide dimer 3 (= 5) inhibited SIRT2 with an IC50 = 176 nM in one assay format and 2.4 mu M in another. Stereochemical determination of symmetrical dimers such as compound 3 pose intriguing and subtle questions in structure elucidation and, as shown in the current work, are perhaps best answered in conjunction with total synthesis.

  DOI：

  10.1021/jo900578j
• 作为产物：
  描述：

  在 palladium on activated charcoal 、 氢气 作用下， 以 正己烷 为溶剂， 反应 3.0h， 以100%的产率得到Takinolide dimer
  参考文献：
  名称：

  Structural and Synthetic Investigations of Tanikolide Dimer, a SIRT2 Selective Inhibitor, and Tanikolide seco-Acid from the Madagascar Marine Cyanobacterium Lyngbya majuscula

  摘要：

  Tanikolide seco-acid 2 and tanikolide dimer 3, the latter a novel and selective SIRT2 inhibitor, were isolated from the Madagascar marine cyanobacterium Lyngbya majuscula. The structure of 2, isolated as the pure R enantiomer, was elucidated by X-rayexperiment in conjunction with NMR and optical rotation data, whereas the depside molecular structure of 3 was initially thought to be a meso compound as established by NMR, MS, and chiral H PLC analyses. Subsequent total synthesis of the three tanikolide dimer stereoisomers 4, 5, and ent-5, followed by chiral GC-MS comparisons with the natural product, showed it to be exclusively the R,R-isomer 5. Tanikolide dimer 3 (= 5) inhibited SIRT2 with an IC50 = 176 nM in one assay format and 2.4 mu M in another. Stereochemical determination of symmetrical dimers such as compound 3 pose intriguing and subtle questions in structure elucidation and, as shown in the current work, are perhaps best answered in conjunction with total synthesis.

  DOI：

  10.1021/jo900578j

文献信息

• Sirtuin Modulators as Inhibitors of Cytomegalovirus
  申请人：The Trustees of Princeton University

  公开号：US20160296523A1

  公开（公告）日：2016-10-13

  Agents and methods of inhibiting or improving the growth of viruses are provided.
• Structural and Synthetic Investigations of Tanikolide Dimer, a SIRT2 Selective Inhibitor, and Tanikolide <i>seco</i>-Acid from the Madagascar Marine Cyanobacterium <i>Lyngbya majuscula</i>
  作者：Marcelino Gutiérrez、Eric H. Andrianasolo、Won Kyo Shin、Douglas E. Goeger、Alexandre Yokochi、Jörg Schemies、Manfred Jung、Dennis France、Susan Cornell-Kennon、Eun Lee、William H. Gerwick

  DOI：10.1021/jo900578j

  日期：2009.8.7

  Tanikolide seco-acid 2 and tanikolide dimer 3, the latter a novel and selective SIRT2 inhibitor, were isolated from the Madagascar marine cyanobacterium Lyngbya majuscula. The structure of 2, isolated as the pure R enantiomer, was elucidated by X-rayexperiment in conjunction with NMR and optical rotation data, whereas the depside molecular structure of 3 was initially thought to be a meso compound as established by NMR, MS, and chiral H PLC analyses. Subsequent total synthesis of the three tanikolide dimer stereoisomers 4, 5, and ent-5, followed by chiral GC-MS comparisons with the natural product, showed it to be exclusively the R,R-isomer 5. Tanikolide dimer 3 (= 5) inhibited SIRT2 with an IC50 = 176 nM in one assay format and 2.4 mu M in another. Stereochemical determination of symmetrical dimers such as compound 3 pose intriguing and subtle questions in structure elucidation and, as shown in the current work, are perhaps best answered in conjunction with total synthesis.