(E)-3-(4-benzyloxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one | 1402550-76-8

• 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: (E)-3-(4-benzyloxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• 英文别名: 2-Propen-1-one, 3-[4-(phenylmethoxy)phenyl]-1-(2,4,6-trihydroxyphenyl)-, (2E)-；(E)-3-(4-phenylmethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• CAS: 1402550-76-8
• 化学式: C₂₂H₁₈O₅
• 分子量: 362.382
• InChiKey: DCSUYOIYDKRKIC-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-benzyloxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one 在 三乙基硅烷 、 palladium 10% on activated carbon 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 0.17h， 以97%的产率得到根皮素
  参考文献：
  名称：

  靶向2型糖尿病，以C-葡萄糖基二氢查耳酮为选择性钠葡萄糖共转运蛋白2（SGLT2）抑制剂：合成和生物学评估

  摘要：

  通过钠葡萄糖共转运蛋白（SGLT）抑制肾脏中的葡萄糖重吸收是治疗2型糖尿病的一种相对较新的策略。相对于SGLT1而言，对SGLT2的选择性抑制对于最小化与SGLT1抑制相关的不利副作用至关重要。合成了C-葡萄糖基二氢查耳酮及其二氢查耳酮和查耳酮前体的文库，并使用基于细胞的葡萄糖吸收荧光测定法测试了它们作为SGLT1 / SGLT2抑制剂的能力。SGLT2的最有效抑制剂（IC 50 = 9–23 nM）是SGLT1的较弱抑制剂（IC 50）= 10–19μM）。他们对葡萄糖转运蛋白的钠依赖性GLUT家族没有影响，最有效的对培养细胞没有急性毒性。通过计算对C-葡萄糖基二氢查耳酮与POPC膜的相互作用进行了建模，从而提供了它不是泛测定干扰化合物的证据。这些结果指向发现是有效且高度选择性的SGLT2抑制剂的结构。

  DOI：

  10.1021/acs.jmedchem.6b01134
• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 盐酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 生成 (E)-3-(4-benzyloxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2,4,6-Trihydroxychalcone Derivatives as Novel Protein Tyrosine Phosphatase 1B Inhibitors

  摘要：

  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.

  DOI：

  10.1111/j.1747-0285.2012.01431.x

文献信息

• Inhibitors of bacterial RNA polymerase: arylpropanoyl, arylpropenoyl, and arylcyclopropanecarboxyl phloroglucinols
  申请人：Rutgers, The State University of New Jersey

  公开号：US10450292B2

  公开（公告）日：2019-10-22

  The invention provides compounds that are inhibitors of bacterial RNA polymerase. The invention also provides compositions comprising such compounds, methods of making such compounds, and methods of using said compounds. The invention has applications in control of bacterial gene expression, control of bacterial growth, antibacterial chemistry, and antibacterial therapy.

  本发明提供的化合物是细菌 RNA 聚合酶的抑制剂。本发明还提供了包含此类化合物的组合物、制造此类化合物的方法以及使用所述化合物的方法。本发明可应用于控制细菌基因表达、控制细菌生长、抗菌化学和抗菌治疗。
• A SIMPLE SYNTHESIS OF SELINONE, AN ANTIFUNGAL COMPONENT OF MONOTES ENGLERI
  作者：Ágnes Kenéz、Laszló Juhász、Sándor Antus

  DOI：10.1515/hc.2002.8.6.543

  日期：2002.1
• 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.
• INHIBITORS OF BACTERIAL RNA POLYMERASE: ARYLPROPANOYL, ARYLPROPENOYL, AND ARYLCYCLOPROPANECARBOXYL PHLOROGLUCINOLS
  申请人：Rutgers, The State University of New Jersey

  公开号：US20190023682A1

  公开（公告）日：2019-01-24

  The invention provides compounds that are inhibitors of bacterial RNA polymerase. The invention also provides compositions comprising such compounds, methods of making such compounds, and methods of using said compounds. The invention has applications in control of bacterial gene expression, control of bacterial growth, antibacterial chemistry, and antibacterial therapy.
• [EN] INHIBITORS OF BACTERIAL RNA POLYMERASE: ARYLPROPANOYL, ARYLPROPENOYL, AND ARYLCYCLOPROPANECARBOXYL PHLOROGLUCINOLS<br/>[FR] INHIBITEURS D'ARN POLYMÉRASE BACTÉRIENNE : ARYL PROPANOYLE, ARYL PROPÉNOYLE ET ARYL CYCLOPROPANE CARBOXYL PHLOROGLUCINOLS
  申请人：UNIV RUTGERS

  公开号：WO2017100645A2

  公开（公告）日：2017-06-15

  The invention provides compounds that are inhibitors of bacterial RNA polymerase. The invention also provides compositions comprising such compounds, methods of making such compounds, and methods of using said compounds. The invention has applications in control of bacterial gene expression, control of bacterial growth, antibacterial chemistry, and antibacterial therapy.