naphthalene-1,6-diyl bis(3,4,5-trihydroxybenzoate) | 1375353-14-2

• 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: naphthalene-1,6-diyl bis(3,4,5-trihydroxybenzoate)
• 英文别名: 1,6-bis[(3,4,5-trihydroxybenzoyl)oxy]naphthalene；[5-(3,4,5-trihydroxybenzoyl)oxynaphthalen-2-yl] 3,4,5-trihydroxybenzoate
• CAS: 1375353-14-2
• 化学式: C₂₄H₁₆O₁₀
• 分子量: 464.385
• InChiKey: ICCXVFVYNQRJSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,6-二羟基萘 在 吡啶 、 氟化氢吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 naphthalene-1,6-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

文献信息

• Promotion of mitochondrial biogenesis by synthetic 1,2‐ or 1,3‐digallates through activation of an energy sensing network
  作者：Taegum Lee、Mi Kyoung Kim、Youhoon Chong

  DOI：10.1002/bkcs.12464

  日期：2022.3

  positions. The relative mitochondrial mass calculated after taking cell sizes into account also confirmed the 1,2- or 1,3-digallates as stimulators of mitochondrial biogenesis. Finally, energy sensing network including AMPK, SIRT1, and PGC-1α was shown to be affected by 1,2- or 1,3-digallates to stimulate mitochondrial biogenesis. Taken together, this study presents a 1,2- or 1,3- digallate as a novel scaffold

  基于表明二没食子酸盐功能可能作为线粒体生物发生诱导剂的新型支架的观察结果，我们制备了一系列二没食子酸盐并在广泛用于 PD 研究（SH-SY5Y 细胞）的体外模型中评估了它们的活性。基于流式细胞术的方法揭示了没食子酸盐对线粒体生物发生的刺激，特别是没食子酸盐在 1,2-或 1,3-位置被取代的那些。在考虑细胞大小后计算的相对线粒体质量也证实了 1,2- 或 1,3-二没食子酸盐是线粒体生物发生的刺激物。最后，包括 AMPK、SIRT1 和 PGC-1α 在内的能量传感网络显示受 1,2-或 1,3-二没食子酸盐的影响，以刺激线粒体生物发生。总之，这项研究提出了 1,2- 或 1，3-二没食子酸盐作为线粒体生物发生刺激物的新型支架。由于线粒体生物发生的诱导剂仍然稀缺，目前的研究结果为对抗神经退行性疾病提供了有价值的工具。
• 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.