2-methoxy-1,4-phenylene bis(3,4,5-trihydroxybenzoate) | 1094451-86-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2-methoxy-1,4-phenylene bis(3,4,5-trihydroxybenzoate)
• 英文别名: 2-methoxy-1,4-bis[(3,4,5-trihydroxybenzoyl)oxy]benzene；[3-methoxy-4-(3,4,5-trihydroxybenzoyl)oxyphenyl] 3,4,5-trihydroxybenzoate
• CAS: 1094451-86-1
• 化学式: C₂₁H₁₆O₁₁
• 分子量: 444.351
• InChiKey: NNYMOXCLLAFSJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-甲氧基对苯二酚 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 生成 2-methoxy-1,4-phenylene 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。
• Novel polyhydroxylated compounds as Fatty Acid Synthase (FASN) inhibitors
  申请人：Fundació Privada Institut d'Investigació Biomédica de Girona - Dr. Josep Trueta

  公开号：EP2019091A1

  公开（公告）日：2009-01-28

  The present invention relates to new polyhydroxylated compounds and, in particular, to its activity as fatty acid synthase (FASN) inhibitors and to their use for the treatment of pathological states for which an inhibitor of this enzyme is indicated. The invention further relate to pharmaceutical compositions containing them and to a process for the preparation of such compounds.

  本发明涉及新的多羟基化合物，特别是其作为脂肪酸合成酶（FASN）抑制剂的活性，以及它们用于治疗需要该酶抑制剂的病理状态。本发明还涉及含有它们的制药组合物以及制备这种化合物的方法。
• Novel Polyhydroxylated Compounds as Fatty Acid Synthase (FASN) Inhibitors
  申请人：Colomer Bosch Ramón

  公开号：US20100190856A1

  公开（公告）日：2010-07-29

  The present invention relates to new polyhydroxylated compounds and, in particular, to its activity as fatty acid synthase (FASN) inhibitors and to their use for the treatment of pathological states for which an inhibitor of this enzyme is indicated. The invention further relate to pharmaceutical compositions containing them and to a process for the preparation of such compounds.

  本发明涉及新的多羟基化合物，特别是它们作为脂肪酸合成酶（FASN）抑制剂的活性以及它们用于治疗需要该酶抑制剂的病理状态。本发明还涉及含有它们的制药组合物以及制备这些化合物的方法。
• NOVEL POLYHYDROXYLATED COMPOUNDS AS FATTY ACID SYNTHASE (FASN) INHIBITORS
  申请人：Fundació Privada Institut d'Investigació Biomédica de Girona - Dr. Josep Trueta

  公开号：EP2170802A1

  公开（公告）日：2010-04-07
• [EN] NOVEL POLYHYDROXYLATED COMPOUNDS AS FATTY ACID SYNTHASE (FASN) INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS POLYHYDROXYLÉS COMME INHIBITEURS D'ACIDE GRAS SYNTHASES (FASN)
  申请人：FUNDACIO PRIVADA INST D INVEST

  公开号：WO2009000864A1

  公开（公告）日：2008-12-31

  [EN] The present invention relates to new polyhydroxylated compounds and, in particular, to its activity as fatty acid synthase (FASN) inhibitors and to their use for the treatment of pathological states for which an inhibitor of this enzyme is indicated. The invention further relate to pharmaceutical compositions containing them and to a process for the preparation of such compounds.
  [FR] La présente invention porte sur de nouveaux composés polyhydroxylés et, en particulier, sur leur activité comme inhibiteurs d'acide gras synthase (FASN) et sur leur utilisation pour le traitement d'états pathologiques pour lesquels un inhibiteur de cette enzyme est indiqué. L'invention concerne en outre les compositions pharmaceutiques les contenant et un procédé pour la préparation de tels composés.