[1,1'-biphenyl]-4,4'-diyl bis(3,4,5-trihydroxybenzoate) | 1094452-15-9

• 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: [1,1'-biphenyl]-4,4'-diyl bis(3,4,5-trihydroxybenzoate)
• 英文别名: 4,4'-bis[(3,4,5-trihydroxybenzoyl)oxy]-1,1'-biphenyl；[4-[4-(3,4,5-trihydroxybenzoyl)oxyphenyl]phenyl] 3,4,5-trihydroxybenzoate
• CAS: 1094452-15-9
• 化学式: C₂₆H₁₈O₁₀
• 分子量: 490.423
• InChiKey: ZLTRQEIZUNCSEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  7
• 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：

  4,4'-bis([3,4,5-tris(benzyloxy)benzoyl]oxy)-1,1'-biphenyl 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70%的产率得到[1,1'-biphenyl]-4,4'-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

• 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。
• Means and methods for treatment of early-onset Parkinson's disease
  申请人：VIB VZW

  公开号：US11202795B2

  公开（公告）日：2021-12-21

  This application relates to the field of neurodegenerative diseases, more particularly to the field of Parkinson's disease. In particular, the disclosure describes that inhibitors reducing FAS activity can be used for treatment of Parkinson's disease, in particular, the treatment of patients suffering from Parkinson's disease having loss of function mutations in PINK1 or PARKIN genes.

  本申请涉及神经退行性疾病领域，尤其是帕金森病领域。特别是，该公开内容描述了降低 FAS 活性的抑制剂可用于治疗帕金森病，尤其是治疗 PINK1 或 PARKIN 基因发生功能缺失突变的帕金森病患者。
• 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
• MEANS AND METHODS FOR TREATMENT OF EARLY-ONSET PARKINSON'S DISEASE
  申请人：VIB VZW

  公开号：US20170319610A1

  公开（公告）日：2017-11-09

  This application relates to the field of neurodegenerative diseases, more particularly to the field of Parkinson's disease. In particular, the disclosure describes that inhibitors reducing FAS activity can be used for treatment of Parkinson's disease, in particular, the treatment of patients suffering from Parkinson's disease having loss of function mutations in PINK1 or PARKIN genes.