(E)-3-hydroxy-4,5,4'-trimethoxystilbene | 1310737-43-9

• 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: (E)-3-hydroxy-4,5,4'-trimethoxystilbene
• 英文别名: DMU-807；2,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenol
• CAS: 1310737-43-9
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: BYIPBHVPCNJJRA-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基-5-羟基苯甲醛 在 正丁基锂 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 hexanes 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (E)-3-hydroxy-4,5,4'-trimethoxystilbene
  参考文献：
  名称：

  Anticancer effects of the metabolic products of the resveratrol analogue, DMU-212: Structural requirements for potency

  摘要：

  The methoxylated trans-stilbene resveratrol analogue, (E)-3,4,5,4'-tetramethoxystilbene (1), has shown promising antiproliferative activity in in vitro cell line and in vivo models. In vivo I gives rise to several metabolic products through demethylation or hydroxylation reactions at the stilbene moiety. In the present study we examined the anticancer activity of 1 and the metabolites (E)-3'-hydroxy-3,4,5,4'-tetramethoxystilbene (2), (E)-4'-hydroxy-3,4,5-trimethoxystilbene (3), (E)-4-hydroxy-3,5,4'-trimethoxystilbene (4) and (E)-3-hydroxy-4,5,4'-trimethoxystilbene (5) by means of cell viability testing, cell cycle analysis, immunostaining and Western blotting. Compounds 1 and 2 exhibited submicromolar toxicity in MCF-7 breast adenocarcinoma and HepG2 hepatoma cells, whereas 3, 4 and 5 were inactive in terms of inhibition of cellular proliferation. Incubation with 1 or 2 at 10 mu M for 24 h induced apoptosis and G2/M cell cycle arrest in MCF-7 and HepG2 cells. Immunostaining of MCF-7 cells for beta-tubulin in the presence of either 1 or 2 revealed shorter localization of the protein around the nucleus, as compared to control cells. Western blot analyses further demonstrated that treatment with either 1 or 2 at concentrations between 30 and 50 mu M for 24 h caused a downregulation in the levels of beta-tubulin and cyclin D1 expression and an upregulation in the levels of p53 expression in MCF-7 and HepG2 cells. 2 further increased the ratio of mRNA levels of the apoptosis-related genes Bax/Bcl-xL in both MCF-7 and HepG2 cells in a dose-dependent manner. We conclude that 2 inhibits HepG2 and MCF-7 cellular proliferation by inducing apoptosis and G2/M arrest through p53 and Bax/Bcl-xL upregulation. Our findings further demonstrate that trimethoxy substitutions along with the presence of a methoxy group at position 4' are necessary for retaining the activity of 1. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.049

文献信息

• [EN] STILBENE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE STILBÈNE ET LEUR UTILISATION POUR LE TRAITEMENT DU CANCER
  申请人：UNIV MONTFORT

  公开号：WO2015166042A1

  公开（公告）日：2015-11-05

  The present application relates to a compound of formula (I) wherein each of R1, R2, R3, R4 or R5 are independently selected from hydrogen, aliphatic, alkoxy, thioalkyl, alkylamino, halogen, hydroxy, cyano, nitro, hydroxyalkyl, alkylcarbonyloxy, alkoxycarbonyl, alkylcarbonyl, haloalkyi, alkylsulfonylamino NH2, NO2, SO2Rx, SORx and COORx, where Rx is hydrogen, aliphatic or aryl, for use in the prevention and/or treatment of cancer. The compounds are particularly provided for the prevention and/or treatment of hormone-induced cancers, such as breast, ovarian, uterine, endometrial and prostate cancer.

  本申请涉及一种具有如下式（I）的化合物，其中R1、R2、R3、R4或R5中的每一个独立地选自氢、脂肪基、烷氧基、硫代烷基、烷基氨基、卤素、羟基、氰基、硝基、羟基烷基、烷基羰基氧基、烷氧羰基、烷基羰基、卤代烷基、烷基磺酰胺基NH2、NO2、SO2Rx、SORx和COORx，其中Rx为氢、脂肪基或芳基，用于预防和/或治疗癌症。这些化合物特别用于预防和/或治疗激素诱导的癌症，如乳腺癌、卵巢癌、子宫癌、子宫内膜癌和前列腺癌。
• GLYCAN THERAPEUTICS AND RELATED METHODS THEREOF
  申请人：Kaleido Biosciences, Inc.

  公开号：EP3071235A1

  公开（公告）日：2016-09-28
• GLYCAN COMPOSITIONS AND USES THEREOF
  申请人：Kaleido Biosciences, Inc.

  公开号：EP3334437A1

  公开（公告）日：2018-06-20
• [EN] GLYCAN THERAPEUTICS AND RELATED METHODS THEREOF<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES DE GYLCANE ET PROCÉDÉS ASSOCIÉS
  申请人：KALEIDO BIOSCIENCES INC

  公开号：WO2016122889A1

  公开（公告）日：2016-08-04

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.
• [EN] GLYCAN COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSITIONS DE GLYCANE ET LEURS UTILISATIONS
  申请人：KALEIDO BIOSCIENCES INC

  公开号：WO2017035412A1

  公开（公告）日：2017-03-02

  Compositions comprising glycan preparations suitable for local administration to non-gut sites containing mucosal tissue, e.g., oral cavity, nasal cavity and vagina are provided. Further provided are methods of using said glycan preparations.