2,7-bis[(3,4,5-tris(tert-butyldimethylsilyloxy)benzoyl)oxy]naphthalene | 1375353-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,7-bis[(3,4,5-tris(tert-butyldimethylsilyloxy)benzoyl)oxy]naphthalene
• 英文别名: [7-[3,4,5-Tris[[tert-butyl(dimethyl)silyl]oxy]benzoyl]oxynaphthalen-2-yl] 3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]benzoate
• CAS: 1375353-29-9
• 化学式: C₆₀H₁₀₀O₁₀Si₆
• 分子量: 1149.96
• InChiKey: CPPIEPCQJUBQLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.58
• 重原子数：
  76
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,7-bis[(3,4,5-tris(tert-butyldimethylsilyloxy)benzoyl)oxy]naphthalene 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到naphthalene-2,7-diyl bis(3,4,5-trihydroxybenzoate)
  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：

  2,7-二羟基萘 、 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以39%的产率得到2,7-bis[(3,4,5-tris(tert-butyldimethylsilyloxy)benzoyl)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