2-methyl-3-[(2E,6E,10E)-3,7,11-trimethyl-12-phenyldodeca-2,6,10-trienyl]naphthalene-1,4-dione | 1310065-54-3

• 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-methyl-3-[(2E,6E,10E)-3,7,11-trimethyl-12-phenyldodeca-2,6,10-trienyl]naphthalene-1,4-dione
• CAS: 1310065-54-3
• 化学式: C₃₂H₃₆O₂
• 分子量: 452.637
• InChiKey: NZFJNVJDMQUCKK-DLPCWNPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2E,6E,10E)-3,7-dimethyl-11-((tetrahydro-2H-pyran-2-yloxy)methyl)dodeca-2,6,10-trienyl acetate 在 copper(l) iodide 、 三氟化硼乙醚 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 2-methyl-3-[(2E,6E,10E)-3,7,11-trimethyl-12-phenyldodeca-2,6,10-trienyl]naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of Novel Vitamin K₂ Analogues with Modification at the ω-Terminal Position and Their Biological Evaluation as Potent Steroid and Xenobiotic Receptor (SXR) Agonists

  摘要：

  Vitamin K-2 is a ligand for a nuclear receptor, steroid and xenobiotic receptor (SXR), that induces the gene expressions of CYP3A4. We synthesized vitamin K-2 analogues with hydroxyl or phenyl groups at the omega-terminal of the side chain. The up-regulation of SXR-mediated transcription of the target gene by the analogues was dependent on the length of the side chain and the hydrophobicity of the omega-terminal residues. Phenyl analogue menaquinone-3 was as active as the known SXR ligand rifampicin.

  DOI：

  10.1021/jm200025f

文献信息

• Synthetic Small Molecules Derived from Natural Vitamin K Homologues that Induce Selective Neuronal Differentiation of Neuronal Progenitor Cells
  作者：Yoshitomo Suhara、Yoshihisa Hirota、Norika Hanada、Shun Nishina、Sachiko Eguchi、Rie Sakane、Kimie Nakagawa、Akimori Wada、Kazuhiko Takahashi、Hiroaki Tokiwa、Toshio Okano

  DOI：10.1021/acs.jmedchem.5b00999

  日期：2015.9.10

  We synthesized new vitamin K2 analogues with ω-terminal modifications of the side chain and evaluated their selective differentiation of neuronal progenitor cells into neurons in vitro. The result of the assay showed that the menaquinone-3 analogue modified with the m-methylphenyl group had the most potent activity, which was twice as great as the control. This finding indicated that it is possible

  我们合成了具有侧链ω-末端修饰的新型维生素K 2类似物，并评估了它们在体外将神经元祖细胞选择性分化为神经元的能力。该测定的结果表明，甲基萘醌-3类似物与改性米甲基苯基组具有最有效的活性，这是两倍大的控制。该发现表明，可以通过改变维生素K 2的结构获得更有效的化合物。
• Synthesis of Novel Vitamin K₂ Analogues with Modification at the ω-Terminal Position and Their Biological Evaluation as Potent Steroid and Xenobiotic Receptor (SXR) Agonists
  作者：Yoshitomo Suhara、Masato Watanabe、Kimie Nakagawa、Akimori Wada、Yoichi Ito、Kazuyoshi Takeda、Kazuhiko Takahashi、Toshio Okano

  DOI：10.1021/jm200025f

  日期：2011.6.23

  Vitamin K-2 is a ligand for a nuclear receptor, steroid and xenobiotic receptor (SXR), that induces the gene expressions of CYP3A4. We synthesized vitamin K-2 analogues with hydroxyl or phenyl groups at the omega-terminal of the side chain. The up-regulation of SXR-mediated transcription of the target gene by the analogues was dependent on the length of the side chain and the hydrophobicity of the omega-terminal residues. Phenyl analogue menaquinone-3 was as active as the known SXR ligand rifampicin.