1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-[4-(benzyloxy)phenyl]prop-2-en-1-one | 1070715-07-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-[4-(benzyloxy)phenyl]prop-2-en-1-one
• 英文别名: 3-(4-benzyloxyphenyl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one；(E)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 1070715-07-9
• 化学式: C₂₆H₂₆O₇
• 分子量: 450.488
• InChiKey: DBBKRINTJBDYRJ-JLHYYAGUSA-N

物化性质

• 沸点：
  646.5±55.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-[4-(benzyloxy)phenyl]prop-2-en-1-one 在 盐酸 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以43.9%的产率得到rac-2-[4-(benzyloxy)phenyl]-5,7-dihydroxychroman-4-one
  参考文献：
  名称：

  A SIMPLE SYNTHESIS OF SELINONE, AN ANTIFUNGAL COMPONENT OF MONOTES ENGLERI

  摘要：

  DOI：

  10.1515/hc.2002.8.6.543
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 31.5h， 生成 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-[4-(benzyloxy)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  首次合成原芹菜酮及其类似物作为有效的细胞毒性剂。

  摘要：

  从火假单胞菌分离的原芹菜酮（1）以前对五种人类癌细胞系显示出显着的细胞毒活性。在持续的结构-活性关系研究中，实现了1的第一个全合成和修饰。评价所有合成的化合物和相关中间体对五种人类癌细胞系HepG2，Hep3B，MDA-MB-231，MCF-7和A549的细胞毒活性。其中24个细胞毒性比1个高2.2-14.2倍，萘基A环类似物显着增强了其活性。

  DOI：

  10.1021/jm070363a

文献信息

• Composition for treating cancer cells and synthetic method for the same
  申请人：Kaohsiung Medical University

  公开号：EP1980248B1

  公开（公告）日：2019-06-12
• Synthesis and evaluation of antiplatelet activity of trihydroxychalcone derivatives
  作者：Li-Ming Zhao、Hai-Shan Jin、Liang-Peng Sun、Hu-Ri Piao、Zhe-Shan Quan

  DOI：10.1016/j.bmcl.2005.08.039

  日期：2005.11

  In an effort to develop potent antiplatelet agents, a series of trihydroxychalcones was synthesized and screened in vitro for their inhibitory effects on washed rabbit platelet aggregation induced by arachidonic acid (100 mu M) and collagen (10 eta g/ml). Of five compounds with potent inhibitory effects on arachidonic acid- and collagen-induced platelet aggregation, compound 4e was found to be the most potent. The structure-activity relationships suggested that antiplatelet activity was governed to a greater extent by the substituent on B ring of the chalcone template, and most of the active compounds had methoxy or dimethoxy groups on B ring. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of 2,4,6-Trihydroxychalcone Derivatives as Novel Protein Tyrosine Phosphatase 1B Inhibitors
  作者：Liang-Peng Sun、Li-Xin Gao、Wei-Ping Ma、Fa-Jun Nan、Jia Li、Hu-Ri Piao

  DOI：10.1111/j.1747-0285.2012.01431.x

  日期：2012.10

  A series of 2,4,6‐trihydroxychalcone derivatives were synthesized and identified as reversible and competitive protein tyrosine phosphatase (PTP) 1B inhibitors with IC50 values in the micromolar range. Compound 4a had the greatest in vitro inhibition activity against PTP1B (IC50 = 0.27 ± 0.01 μm) and the best selectivity (6.9‐fold) for PTP1B relative to T‐cell protein tyrosine phosphatases. The compounds identified herein provide a foundation on which to design specific inhibitors of PTP1B and other PTPs.