2,6-bis([3,4,5-tris(benzyloxy)benzoyl]oxy)naphthalene | 1084333-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-bis([3,4,5-tris(benzyloxy)benzoyl]oxy)naphthalene
• 英文别名: 2,6-di(3,4,5-tribenzyloxybenzoyloxy)naphthalene
• CAS: 1084333-78-7
• 化学式: C₆₆H₅₂O₁₀
• 分子量: 1005.13
• InChiKey: BYIDRWMEKREKKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.75
• 重原子数：
  76.0
• 可旋转键数：
  22.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,6-bis([3,4,5-tris(benzyloxy)benzoyl]oxy)naphthalene 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 以54%的产率得到2,6-bis[(3,4,5-trihydroxybenzoyl)oxy]naphthalene
  参考文献：
  名称：

  New Synthetic Inhibitors of Fatty Acid Synthase with Anticancer Activity

  摘要：

  Fatty acid synthase (FASN) is a lipogenic enzyme that is highly expressed in different human cancers. Here we report the development of a new series of polyphenolic compounds 5-30 that have been evaluated for their cytotoxic capacity in SK-Br3 cells, a human breast cancer cell line with high FASN expression. The compounds with art IC50 < 50 mu M have been tested for their ability to inhibit FASN activity. Among them, derivative 30 blocks the 90% of FASN activity at low concentration (4 mu M), is highly cytotoxic in a broad panel of tumor cells, induces apoptosis, and blocks the activation of HER2, AKT, and ERK pathways. Remarkably, 30 does not activate carnitine palmitoyltransferase-1 (CPT-1) nor induces in mice weight loss, which are the main drawbacks of other previously described FASN inhibitors. Thus, FASN inhibitor 30 may aid the validation of this enzyme as a therapeutic target for the treatment of cancer.

  DOI：

  10.1021/jm2016045
• 作为产物：
  描述：

  2,6-萘二酚 、 3,4,5-tris(benzyloxy)benzoyl chloride 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 以22.8%的产率得到2,6-bis([3,4,5-tris(benzyloxy)benzoyl]oxy)naphthalene
  参考文献：
  名称：

  Chemiluminescence Change of Polyphenol Dendrimers with Different Core Molecules

  摘要：

  Second generation polyphenol dendrimers (PDs) with different core molecules were synthesized, and their chemiluminescence (CL) was measured by reacting the PDs with H2O2 under alkaline conditions. All of the PDs showed a strong CL, more than 120-fold greater than that of gallic acid. Various CL intensities of the PDs were obtained using different core molecules in the PDs. The distance between each dendron in the PD structure is crucial in the PD CL intensity.

  DOI：

  10.1021/ol802129a