4-[2-(4,8-dimethyl-nonyl)-2,5,7,8-tetramethyl-chroman-6-yloxy]-butyric acid | 1187946-10-6

• 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: 4-[2-(4,8-dimethyl-nonyl)-2,5,7,8-tetramethyl-chroman-6-yloxy]-butyric acid
• 英文别名: 4-[[(2S)-2-(4,8-dimethylnonyl)-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl]oxy]butanoic acid
• CAS: 1187946-10-6
• 化学式: C₂₈H₄₆O₄
• 分子量: 446.671
• InChiKey: JNZFJOGTYRRPNQ-GPIXMLASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-[2-(4,8-dimethyl-non-1-enyl)-2,5,7,8-tetramethyl-chroman-6-yloxy]-butyric acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 生成 4-[2-(4,8-dimethyl-nonyl)-2,5,7,8-tetramethyl-chroman-6-yloxy]-butyric acid
  参考文献：
  名称：

  α-Tocopheryl Succinate as a Scaffold to Develop Potent Inhibitors of Breast Cancer Cell Adhesion

  摘要：

  This study is aimed at the pharmacological exploitation of a-tocopheryl succinate (1) to develop potent antiadhesion agents. Considering the structural cooperativity between the phytyl chain and the carboxylic terminus in determining the antiadhesion activity, our structural optimization led to compound 5 ([2-(4,8-dimethyl-non-1-enyl)-2,5,7,8-tetramethyl-chroman-6-yloxy]-acetic acid), which exhibited an-order-of-magnitude higher potency than I in blocking the adhesion of 4T1 metastatic breast cancer cells to extracellular matrix proteins (IC50, 0.6 mu M versus 10 mu M). Evidence indicates that the ability of compound 5 to block cell adhesion and migration was attributable to its effect on disrupting focal adhesion and actin cytoskeletal integrity by facilitating the degradation of focal adhesion kinase. Interactions between tumor cells and the ECM in the tumor microenvironment have been increasingly recognized as critical modulators of the metastatic potential of tumor cells. Consequently, the ability of compound 5 to block such interactions provides a unique pharmacological tool to shed light onto mechanisms that govern cell adhesion and tumor metastasis.

  DOI：

  10.1021/jm9002457