methyl 1,4-bis[(3,4,5-trihydroxybenzoyl)oxy]-2-naphthoate | 1375353-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1,4-bis[(3,4,5-trihydroxybenzoyl)oxy]-2-naphthoate
• 英文别名: Methyl 1,4-bis[(3,4,5-trihydroxybenzoyl)oxy]naphthalene-2-carboxylate
• CAS: 1375353-13-1
• 化学式: C₂₆H₁₈O₁₂
• 分子量: 522.422
• InChiKey: OBABNULXXIIVEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  200
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3,4,5-tris((tert-butyldimethylsilyl)oxy)benzoic acid 在 吡啶 、 草酰氯 、 氟化氢吡啶 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 methyl 1,4-bis[(3,4,5-trihydroxybenzoyl)oxy]-2-naphthoate
  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

文献信息

• New Synthetic Inhibitors of Fatty Acid Synthase with Anticancer Activity
  作者：Carlos Turrado、Teresa Puig、Javier García-Cárceles、Marta Artola、Bellinda Benhamú、Silvia Ortega-Gutiérrez、Joana Relat、Gloria Oliveras、Adriana Blancafort、Diego Haro、Pedro F. Marrero、Ramón Colomer、María L. López-Rodríguez

  DOI：10.1021/jm2016045

  日期：2012.6.14

  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.