ethyl 2,3,3-tri-(4-hydroxy-3-methoxyphenyl)propanoate | 1415803-96-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 2,3,3-tri-(4-hydroxy-3-methoxyphenyl)propanoate
• 英文别名: ethyl 2,3,3-tris(4-hydroxy-3-methoxyphenyl)propanoate；quebecol；Ethyl 2,3,3-tris(4-hydroxy-3-methoxyphenyl)propanoate
• CAS: 1415803-96-1
• 化学式: C₂₆H₂₈O₈
• 分子量: 468.504
• InChiKey: LAYSJOVFMDCRMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,3-tri-(4-hydroxy-3-methoxyphenyl)propanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以84%的产率得到4,4',4''-(3-hydroxypropane-1,1,2-triyl)tris(2-methoxyphenol)
  参考文献：
  名称：

  Anti-inflammatory properties of quebecol and its derivatives

  摘要：

  Herein we report our results on the anti-inflammatory activity of quebecol, a polyphenolic compound discovered in maple syrup. Bioassays demonstrated that quebecol has an anti-inflammatory effect on LPS-induced NF-kappa B activation and inhibits the secretion of two pro-inflammatory cytokines, IL-6 and TNF-alpha. We also prepared and tested precursors of quebecol and its derivatives corresponding to its substructures of interest, with the aim to study the structure-activity relationships. Comparing the results obtained for all tested compounds allowed the identification of the main moiety responsible for the anti-inflammatory activity of quebecol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.096
• 作为产物：
  描述：

  香草基扁桃酸乙酯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四溴化碳 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 110.0 ℃ 、1.97 MPa 条件下， 反应 50.08h， 生成 ethyl 2,3,3-tri-(4-hydroxy-3-methoxyphenyl)propanoate
  参考文献：
  名称：

  Total synthesis of quebecol

  摘要：

  We report here the total synthesis of quebecol, a new polyphenolic compound with potential applications recently isolated from maple syrup and produced during the condensation of the tree acer saccharum's sap. The synthetic approach we developed involves, as key steps, the formation of a dibromoalkene from an alpha-ketoester precursor followed by a double Suzuki-Miyaura reaction to unite the three aromatic rings of the target compound on a tetrasubstituted olefin precursor. Our methodology is an efficient pathway to the target compound and leads the way for future analogs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.048

文献信息

• Synthesis and antiproliferative activities of quebecol and its analogs
  作者：Kasiviswanadharaju Pericherla、Amir Nasrolahi Shirazi、V. Kameshwara Rao、Rakesh K. Tiwari、Nicholas DaSilva、Kellen T. McCaffrey、Yousef A. Beni、Antonio González-Sarrías、Navindra P. Seeram、Keykavous Parang、Anil Kumar

  DOI：10.1016/j.bmcl.2013.07.058

  日期：2013.10

  Simple and efficient synthesis of quebecol and a number of its analogs was accomplished in five steps. The synthesized compounds were evaluated for antiproliferative activities against human cervix adenocarcinoma (HeLa), human ovarian carcinoma (SK-OV-3), human colon carcinoma (HT-29), and human breast adenocarcinoma (MCF-7) cancer cell lines. Among all the compounds, 7c, 7d, 7f, and 8f exhibited antiproliferative

  quebecol 及其许多类似物的简单有效合成分五个步骤完成。评估合成的化合物对人子宫颈腺癌 (HeLa)、人卵巢癌 (SK-OV-3)、人结肠癌 (HT-29) 和人乳腺癌 (MCF-7) 癌细胞系的抗增殖活性。在所有化合物中，7c、7d、7f和8f对四种测试细胞系表现出抗增殖活性，72 小时后在 75 μM 下抑制超过 80%，而化合物7b和7g对 MCF-7 细胞系更具选择性。化合物7c、7d的 IC 50值和7f分别是针对 MCF-7 细胞系的 85.1 μM、78.7 μM 和 80.6 μM，显示出比合成和分离的 quebecol 略高的抗增殖活性，对 MCF-7的 IC 50值为 104.2 μM。
• PHENOLIC COMPOUNDS WITH ANTIOXIDANT AND ANTI-CANCER PROPERTIES, ANALOGS AND SYNTHESIS THEREOF
  申请人：Seeram Navindra

  公开号：US20140336259A1

  公开（公告）日：2014-11-13

  The present document describes a phytochemical isolated from maple syrup and composition comprising the same. More specifically, the document describes an antioxidant phytochemical compound, derivates thereof, and composition comprising the same. The document also describes a process of synthesizing the antioxidant phytochemical compound.

  本文件描述了从枫糖浆中分离出的植物化学物质及其组成物。更具体地，该文件描述了一种抗氧化剂植物化合物，其衍生物以及包含其的组成物。该文件还描述了一种合成抗氧化剂植物化合物的过程。
• Anti-inflammatory properties of quebecol and its derivatives
  作者：Sébastien Cardinal、Jabrane Azelmat、Daniel Grenier、Normand Voyer

  DOI：10.1016/j.bmcl.2015.11.096

  日期：2016.1

  Herein we report our results on the anti-inflammatory activity of quebecol, a polyphenolic compound discovered in maple syrup. Bioassays demonstrated that quebecol has an anti-inflammatory effect on LPS-induced NF-kappa B activation and inhibits the secretion of two pro-inflammatory cytokines, IL-6 and TNF-alpha. We also prepared and tested precursors of quebecol and its derivatives corresponding to its substructures of interest, with the aim to study the structure-activity relationships. Comparing the results obtained for all tested compounds allowed the identification of the main moiety responsible for the anti-inflammatory activity of quebecol. (C) 2015 Elsevier Ltd. All rights reserved.
• Total synthesis of quebecol
  作者：Sébastien Cardinal、Normand Voyer

  DOI：10.1016/j.tetlet.2013.07.048

  日期：2013.9

  We report here the total synthesis of quebecol, a new polyphenolic compound with potential applications recently isolated from maple syrup and produced during the condensation of the tree acer saccharum's sap. The synthetic approach we developed involves, as key steps, the formation of a dibromoalkene from an alpha-ketoester precursor followed by a double Suzuki-Miyaura reaction to unite the three aromatic rings of the target compound on a tetrasubstituted olefin precursor. Our methodology is an efficient pathway to the target compound and leads the way for future analogs. (C) 2013 Elsevier Ltd. All rights reserved.