1,2-bis[[3,4,5-tris(benzyloxy)benzoyl]oxy]benzene | 583041-67-2

• 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: 1,2-bis[[3,4,5-tris(benzyloxy)benzoyl]oxy]benzene
• 英文别名: 1,2-phenylene bis(3,4,5-tris(benzyloxy)benzoate)；[2-[3,4,5-tris(phenylmethoxy)benzoyl]oxyphenyl] 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 583041-67-2
• 化学式: C₆₂H₅₀O₁₀
• 分子量: 955.073
• InChiKey: NTVJNALZMOOCIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  72
• 可旋转键数：
  24
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1,2-bis[[3,4,5-tris(benzyloxy)benzoyl]oxy]benzene 在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 1,2-bis[(3,4,5-trihydroxybenzoyl)oxy]benzene
  参考文献：
  名称：

  通过激活能量传感网络，合成 1,2-或 1,3-二甘醇盐促进线粒体生物发生

  摘要：

  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。

  DOI：

  10.1002/bkcs.12464
• 作为产物：
  描述：

  没食子酸甲酯 在 4-二甲氨基吡啶 、 水 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,2-bis[[3,4,5-tris(benzyloxy)benzoyl]oxy]benzene
  参考文献：
  名称：

  通过激活能量传感网络，合成 1,2-或 1,3-二甘醇盐促进线粒体生物发生

  摘要：

  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。

  DOI：

  10.1002/bkcs.12464

文献信息

• Plasminogen Activator Inhibitor-1 Inhibitors and Methods of Use Thereof to Modulate Lipid Metabolism
  申请人：Lawrence Daniel A.

  公开号：US20100137194A1

  公开（公告）日：2010-06-03

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  本发明涉及纤溶酶原激活剂-1（PAI-1）抑制剂化合物及其在治疗任何与升高的PAI-1相关的疾病或病状中的应用。本发明包括但不限于使用这些化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的病症。
• PLASMINOGEN ACTIVATOR INHIBITOR-1 INHIBITORS AND METHODS OF USE THEREOF TO MODULATE LIPID METABOLISM
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20160009748A1

  公开（公告）日：2016-01-14

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  本发明涉及纤溶酶原激活物-1（PAI-1）抑制剂化合物及其在治疗与升高的PAI-1相关的任何疾病或病况中的用途。本发明包括但不限于使用这样的化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的病症。
• 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.
• Synthesis of poly (3,4,5-trihydroxybenzoate ester) dendrimers and their chemiluminescence
  作者：Manabu Nakazono、Li Ma、Kiyoshi Zaitsu

  DOI：10.1016/s0040-4039(02)01959-7

  日期：2002.11

  Gallic acid (GA) and gallic acid methyl ester (GM), polyphenol chemiluminescence (CL) compounds, produces light in the presence of alkali and hydrogen peroxide. We synthesized first-generation polyphenol dendrimers with GA units in the periphery and measured their CL for developing a polyphenol compound which has a strong CL intensity. The CL intensities of the poly (3,4,5-trihydroxybenzoate ester) dendrimers 4 and 8 in MeOH are approximately 400- and 600-fold stronger than that of GA, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Mimic catechins to develop selective MMP-2 inhibitors
  作者：Antonella Di Pizio、Mariangela Agamennone、Antonio Laghezza、Fulvio Loiodice、Paolo Tortorella

  DOI：10.1007/s00706-018-2237-4

  日期：2018.7

  Matrix metalloproteinase 2 (MMP-2) is a well-known anticancer target belonging to the MMP family. Because of the bilateral role of MMPs in cancer, developing highly selective MMP-2 inhibitors is a current challenge. In this paper, we investigated the binding modes of green tea polyphenols epigallocatechin gallate and epicatechin into the active site of the MMP-2 enzyme. The structure-based analysis allowed the optimization of these hits and hence led to a better lead candidate. Moreover, using a pharmacophore model, we screened FooDB compounds and selected food components as potential MMP-2 inhibitors. The search for food-derived compounds that target this enzyme may represent a strategy to identify new lead molecules with improved safety profiles and provide indications about possible functional foods.[GRAPHICS].