2-((2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dienyl)-3-methylnaphthalene-1,4-dione

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-((2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dienyl)-3-methylnaphthalene-1,4-dione
• 英文别名: 2-[(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dienyl]-3-methylnaphthalene-1,4-dione
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: XEBFMYJUEVJEKQ-GGQZXFEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dienyl)-3-methylnaphthalene-1,4-dione 在 manganese(IV) oxide 作用下， 以78%的产率得到(2E,6E)-8-(1,4-dihydro-2-methyl-1,4-dioxonaphthalen-3-yl)-2,6-dimethylocta-2,6-dienal
  参考文献：
  名称：

  通过引入杂原子和苯基诱导神经元祖细胞的高选择性神经元分化制备的新型合成维生素K类似物的合成。

  摘要：

  我们合成了新的维生素K 2类似物，在侧链中掺入了杂原子和芳香环，并评估了它们对体外神经元祖细胞选择性分化的影响。结果表明，带有对氟苯胺的甲萘醌-2类似物具有最强的活性，是对照的两倍以上。此外，神经元的选择性是对照的3倍以上。

  DOI：

  10.1021/acs.jmedchem.6b01717
• 作为产物：
  描述：

  1,4-二羟基-2-甲基萘 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 三氟化硼乙醚 、 水杨酸 作用下， 生成 2-((2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dienyl)-3-methylnaphthalene-1,4-dione
  参考文献：
  名称：

  通过引入杂原子和苯基诱导神经元祖细胞的高选择性神经元分化制备的新型合成维生素K类似物的合成。

  摘要：

  我们合成了新的维生素K 2类似物，在侧链中掺入了杂原子和芳香环，并评估了它们对体外神经元祖细胞选择性分化的影响。结果表明，带有对氟苯胺的甲萘醌-2类似物具有最强的活性，是对照的两倍以上。此外，神经元的选择性是对照的3倍以上。

  DOI：

  10.1021/acs.jmedchem.6b01717

文献信息

• Design and synthesis of biologically active analogues of vitamin K2: Evaluation of their biological activities with cultured human cell lines
  作者：Yoshitomo Suhara、Yoshihisa Hirota、Kimie Nakagawa、Maya Kamao、Naoko Tsugawa、Toshio Okano

  DOI：10.1016/j.bmc.2007.12.025

  日期：2008.3.15

  Novel omega-oxygenated vitamin K(2) analogues were efficiently synthesized and their biological activities were evaluated. Some were biologically active and the side-chain played an important role in gamma-carboxylation and apoptosis-inducing activity. The results provide useful information on the structure-activity relationship of vitamin K(2) analogues for the development of new drugs.

  新型的ω-氧化的维生素K（2）类似物被有效地合成，并对其生物学活性进行了评估。一些具有生物活性，并且侧链在γ-羧化和诱导细胞凋亡的活性中起重要作用。结果提供了有关维生素K（2）类似物的结构-活性关系的新药开发有用的信息。
• Efficient synthesis and biological evaluation of ω-oxygenated analogues of vitamin K2: Study of modification and structure–activity relationship of vitamin K2 metabolites
  作者：Yoshitomo Suhara、Aya Murakami、Maya Kamao、Shino Mimatsu、Kimie Nakagawa、Naoko Tsugawa、Toshio Okano

  DOI：10.1016/j.bmcl.2006.12.082

  日期：2007.3

  Novel omega-oxygenated vitamin K-2 analogues, which are candidates for metabolites of vitamin K-2 homologues, were efficiently synthesized and their apoptosis-inducing activity was evaluated. We revealed that some of those analogues were biologically active and the side-chain part played an important role in apoptosis-inducing activity. Our results can provide useful information to develop the structure-activity relationship of vitamin K-2 analogues for new drugs based on vitamin K. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Novel Synthetic Vitamin K Analogues Prepared by Introduction of a Heteroatom and a Phenyl Group That Induce Highly Selective Neuronal Differentiation of Neuronal Progenitor Cells
  作者：Kimito Kimura、Yoshihisa Hirota、Shigefumi Kuwahara、Atsuko Takeuchi、Chisato Tode、Akimori Wada、Naomi Osakabe、Yoshitomo Suhara

  DOI：10.1021/acs.jmedchem.6b01717

  日期：2017.3.23

  We synthesized novel vitamin K2 analogues that incorporated a heteroatom and an aromatic ring in the side chain and evaluated their effect on the selective differentiation of neuronal progenitor cells into neurons in vitro. The results showed that a menaquinone-2 analogue bearing a p-fluoroaniline had the most potent activity, which was more than twice as great as the control. In addition, the neuronal

  我们合成了新的维生素K 2类似物，在侧链中掺入了杂原子和芳香环，并评估了它们对体外神经元祖细胞选择性分化的影响。结果表明，带有对氟苯胺的甲萘醌-2类似物具有最强的活性，是对照的两倍以上。此外，神经元的选择性是对照的3倍以上。