2,4'-二甲氧基-2-羟基查尔酮 | 32272-18-7

• 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
• 中文名称: 2,4'-二甲氧基-2-羟基查尔酮
• 英文名称: 2,4'-Dimethoxy-2-hydroxychalcone
• 英文别名: (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2-methoxyphenyl)-prop-2-en-1-one；2'-hydroxy-2,4'-dimethoxychalcone；2'-hydroxy-2,4'-dimethoxychalkone；2'-hydroxy-4',2-dimethoxychalcone；2'-hydroxy-2,4'-dimethoxy-trans-chalcone；2'-hydroxy-2,4'-dimethoxy-chalcone；2,4'-Dimethoxy-2'-hydroxychalcone；(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
• CAS: 32272-18-7
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: YSOOAJSZRVJKCW-JXMROGBWSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  485.7±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

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：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4'-二甲氧基-2-羟基查尔酮 在 sodium hydroxide 、 双氧水 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 50.0h， 生成 2'-benzyloxy-2,4'-dimethoxychalkone epoxide
  参考文献：
  名称：

  Rani, Indu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 361 - 362

  摘要：

  DOI：
• 作为产物：
  描述：

  水杨醛 在 sodium hydroxide 作用下， 生成 2,4'-二甲氧基-2-羟基查尔酮
  参考文献：
  名称：

  2'-羟基-和2'-甲氧基-黄酮

  摘要：

  DOI：

  10.1039/jr9550000166

文献信息

• Synthesis and Screening of Human Monoamine Oxidase-A Inhibitor Effect of New 2-Pyrazoline and Hydrazone Derivatives
  作者：Begüm Evranos-Aksöz、İpek Baysal、Samiye Yabanoğlu-Çiftçi、Teodora Djikic、Kemal Yelekçi、Gülberk Uçar、Rahmiye Ertan

  DOI：10.1002/ardp.201500212

  日期：2015.10

  for their inhibitory activities toward the A and B isoforms of human monoamine oxidase (MAO). Except for 3k and 6c, all compounds were found to be competitive, reversible, and selective inhibitors for either one of the isoforms (hMAO‐A or MAO‐B). Compounds 3k and 6c were found to be competitive, reversible, but non‐selective MAO inhibitors. Compound 6h showed hMAO‐B inhibitory activity whereas the others

  通过各种查耳酮与酰肼化合物在乙醇中的反应制备了一组 3,5-二芳基-2-吡唑啉和腙衍生物。合成了二十个原始化合物。这些原始化合物中有 10 个具有吡唑啉结构，其中 9 个原始化合物具有腙结构，这些原始化合物之一具有查耳酮结构。通过IR、1H NMR、13C NMR、质谱数据和元素分析对化合物进行结构鉴定。测试了这些化合物对人单胺氧化酶 (MAO) 的 A 和 B 亚型的抑制活性。除 3k 和 6c 外，所有化合物均被发现对任一亚型（hMAO-A 或 MAO-B）均具有竞争性、可逆性和选择性抑制剂。发现化合物 3k 和 6c 具有竞争性、可逆性、但非选择性 MAO 抑制剂。化合物 6h 显示出 hMAO-B 抑制活性，而其他化合物则有效抑制 hMAO-A。化合物 5c 显示出比标准药物吗氯贝胺更高的选择性。根据实验 Ki 值，化合物 6i、6d 和 6a 对 hMAO-A 表现出最高的抑制活性。AutoDock
• Inhibitors against the production and release of inflammatory cytokines
  申请人：——

  公开号：US20040259877A1

  公开（公告）日：2004-12-23

  A medicament having inhibitory activity against NF-&kgr;B activation, which comprises a compound represented by the following general formula (I) or a pharmacologically acceptable salt as an active ingredient: 1 wherein X represents a connecting group, A represents hydrogen atom or acetyl group, E represents an aryl group or a heteroaryl group, and ring X represents an arene or a heteroarene.

  一种具有抑制NF-&kgr;B激活活性的药物，其包括以下通式（I）所表示的化合物或其药学上可接受的盐作为活性成分：1其中X表示连接基，A表示氢原子或乙酰基，E表示芳基或杂芳基，环X表示芳烃或杂芳烃。
• INFLAMMATORY CYTOKINE RELEASE INHIBITOR
  申请人：MUTO Susumu

  公开号：US20100274051A1

  公开（公告）日：2010-10-28

  A medicament having inhibitory activity against NF-κB activation, which comprises a compound represented by the following general formula (I) or α pharmacologically acceptable salt as an active ingredient: wherein X represents a connecting group, A represents hydrogen atom or acetyl group, E represents an aryl group or a heteroaryl group, and ring X represents an arene or a heteroarene.

  一种具有对NF-κB激活抑制活性的药物，其包括以下通式（I）所代表的化合物或α药理学上可接受的盐作为活性成分：其中，X代表连接基，A代表氢原子或乙酰基，E代表芳基或杂芳基，环X代表芳烃或杂芳烃。
• INHIBITORS AGAINST THE PRODUCTION AND RELEASE OF INFLAMMATORY CYTOKINES
  申请人：Institute of Medicinal Molecular Design, Inc.

  公开号：EP1352650A1

  公开（公告）日：2003-10-15

  A medicament having inhibitory activity against NF- κ B activation, which comprises a compound represented by the following general formula (I) or a pharmacologically acceptable salt as an active ingredient: wherein X represents a connecting group, A represents hydrogen atom or acetyl group, E represents an aryl group or a heteroaryl group, and ring X represents an arene or a heteroarene.

  一种对 NF-κ B 活化具有抑制活性的药物，其活性成分包括下通式(I)所代表的化合物或药理学上可接受的盐： 其中，X 代表连接基团，A 代表氢原子或乙酰基，E 代表芳基或杂芳基，环 X 代表芳炔或杂芳炔。
• ——
  作者：Christelle Pouget、Catherine Fagnere、Jean‐Philippe Basly、Anne‐Elise Besson、Yves Champavier、Gerard Habrioux、Albert‐Jose Chulia

  DOI：10.1023/a:1014490817731

  日期：——

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.