2'-hydroxy-4',6'-dimethoxy-4-methylchalcone | 76554-25-1

• 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: 2'-hydroxy-4',6'-dimethoxy-4-methylchalcone
• 英文别名: 2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methylphenyl)-；1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one
• CAS: 76554-25-1
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: PWVBSDQARMAGHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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'-hydroxy-4',6'-dimethoxy-4-methylchalcone 在 吡啶 作用下， 以 甲醇 为溶剂， 生成 5,7-dimethoxy-2-(p-tolyl)-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  从手性前体中减员强化的脱氮和绝对不对称合成黄酮

  摘要：

  从溶剂中重结晶后，七个外消旋的5,7-二甲氧基黄酮酮提供了凝聚物晶体。研究了三种方法来实现基于手性团聚体系统动态结晶的不对称转化。第一个是通过减磨增强的去消旋作用使外消旋黄烷酮手性对称性破坏。在碱（1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU））和玻璃珠存在下，外消旋黄烷酮在少量丙醇中的连续悬浮促进了手性对称性的破坏并将黄烷酮转化为晶体具有78％至99％ee的（+）-或（-）-对映体。第二种方法涉及中间体醛醇缩合产物的环化，以产生具有90％ee的旋光性黄烷酮，其中涉及可逆的oxa-Michael加成反应以及减磨作用。

  DOI：

  10.1021/acs.cgd.0c00955
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 10.25h， 生成 2'-hydroxy-4',6'-dimethoxy-4-methylchalcone
  参考文献：
  名称：

  Discovery of flavone-derivatives as the new skeleton of transient receptor potential vanilloid 3 channel antagonists

  摘要：

  DOI：

  10.1016/j.bmcl.2023.129577

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS COMPRISING CDK INHIBITORS AND METHODS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS ET COMPOSITIONS COMPRENANT DES INHIBITEURS DES CDK ET MÉTHODES DE TRAITEMENT DU CANCER
  申请人：UNIV GEORGIA STATE RES FOUND

  公开号：WO2010129858A1

  公开（公告）日：2010-11-11

  Disclosed herein are compounds suitable for use as antitumor agents, methods for treating cancer wherein the disclosed compounds are used in making a medicament for the treatment of cancer, methods for treating a tumor comprising, administering to a subject a composition comprising one or more of the disclosed cytotoxic agents, and methods for preparing the disclosed antitumor agents.

  本文披露了适用作抗肿瘤药剂的化合物，用于治疗癌症的方法，其中所披露的化合物用于制备治疗癌症的药物，治疗肿瘤的方法包括向受试者施用包含一种或多种所披露的细胞毒性药剂的组合物，以及制备所披露的抗肿瘤药剂的方法。
• Synthesis, Biological Evaluation and Molecular Modelling of 2′-Hydroxychalcones as Acetylcholinesterase Inhibitors
  作者：Sri Sukumaran、Chin Chee、Geetha Viswanathan、Michael Buckle、Rozana Othman、Noorsaadah Abd. Rahman、Lip Chung

  DOI：10.3390/molecules21070955

  日期：——

  A series of 2′-hydroxy- and 2′-hydroxy-4′,6′-dimethoxychalcones was synthesised and evaluated as inhibitors of human acetylcholinesterase (AChE). The majority of the compounds were found to show some activity, with the most active compounds having IC50 values of 40–85 µM. Higher activities were generally observed for compounds with methoxy substituents in the A ring and halogen substituents in the

  合成了一系列 2'-羟基-和 2'-羟基-4',6'-二甲氧基查尔酮，并将其作为人乙酰胆碱酯酶 (AChE) 的抑制剂进行评估。发现大多数化合物具有一定的活性，活性最强的化合物的 IC50 值为 40–85 µM。对于在 A 环中具有甲氧基取代基和在 B 环中具有卤素取代基的化合物，通常观察到更高的活性。对最活跃的化合物的动力学研究表明，它们作为混合型抑制剂，这与分子模型研究的结果一致，这表明它们与外周阴离子位点和 AChE 峡谷区域的残基相互作用。
• COMPOUNDS AND COMPOSITIONS COMPRISING CDK INHIBITORS AND METHODS FOR TREATING CANCER
  申请人：Xu Wen Fang

  公开号：US20120121692A1

  公开（公告）日：2012-05-17

  Disclosed herein are compounds suitable for use as antitumor agents, methods for treating cancer wherein the disclosed compounds are used in making a medicament for the treatment of cancer, methods for treating a tumor comprising, administering to a subject a composition comprising one or more of the disclosed cytotoxic agents, and methods for preparing the disclosed antitumor agents.

  本文披露了适用于作为抗肿瘤剂的化合物，其中所披露的化合物用于制备用于治疗癌症的药物，治疗肿瘤的方法包括向受试者投与含有所披露的细胞毒性药物之一或多个的组合物，以及制备所披露的抗肿瘤剂的方法。
• Silica supported-double metal cyanides (DMCs): A green and highly efficient catalytic protocol for isomerisation of 2′-hydroxychalcones to flavanones
  作者：Naseem Ahmed、Naveen Kumar Konduru、Praveen、Anand Kumar、Kamaluddin

  DOI：10.1016/j.molcata.2013.03.009

  日期：2013.7

  Four different double metal cyanides (NiHCFe, CrHCFe, MnHCFe and ZnHCFe) were synthesized, followed by adsorbed on silica gel and used as Lewis acid catalyst in the isomerisation of substituted 2'-hydroxychalcones to flavanones under solvent-free (dry) condition. Optimization of the reaction condition, temperature effects, DMC catalysts loading and re-useable catalytic activity were further studied during the reaction. Among these catalysts, NiHCFe at 35 mol% loading gave excellent yield (90%) at 100 degrees C temperature in 1.15 h. Catalyst (NiHCFe) easily recovered and re-used six times without much loss of its catalytic activity which gave 80-85% product yields each time. However, these DMCs were failed to give product in the solution phase even prolonging the reaction time at reflux temperature. Similarly, isomerization of substituted 2'-aminochalcones gave 2-5% yields either in solution phase or under solvent-free condition. (C) 2013 Elsevier B.V. All rights reserved.
• COMPOUNDS AND COMPOSITIONS COMPRISING CDK INHIBITORS AND METHODS FOR THE TREATMENT OF CANCER
  申请人：Georgia State University Research Foundation, Inc.

  公开号：EP2429292A1

  公开（公告）日：2012-03-21