(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-m-tolylprop-2-en-1-one | 1197288-76-8

• 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)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-m-tolylprop-2-en-1-one
• 英文别名: (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(3-methylphenyl)prop-2-en-1-one
• CAS: 1197288-76-8
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: PJZUBTYSDRPKIN-BQYQJAHWSA-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

• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 3-甲基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以32%的产率得到(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-m-tolylprop-2-en-1-one
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Chalcone Leading to 3-Hydroxy-4,3′,4′,5′-tetramethoxychalcone and Its Analogues as Potent Nuclear Factor κB Inhibitors and Their Anticancer Activities

  摘要：

  Chalcone is a privileged structure, demonstrating promising anti-inflammatory and anticancer activities. One potential mechanism is to suppress nuclear factor kappa B (NF-kappa B) activation. The structures of chalcone-based NF-kappa B inhibitors vary significantly that there is minimum information about their structure-activity relationships (SAR). This study aims to establish SAR of chalcone-based compounds to NF-kappa B inhibition, to explore the feasibility of developing simple chalcone-based potent NF-kappa B inhibitors, and to evaluate their anticancer activities. Three series of chalcones were synthesized in one to three steps with the key step being aldol condensation. These candidates demonstrated a wide range of NF-kappa B inhibitory activities, some of low micromolar potency, establishing that structural complexity is not required for NF-kappa B inhibition. Lead compounds also demonstrate potent cytotoxicity against lung cancer cells. Their cytotoxicities correlate moderately well with their NF-kappa B inhibitory activities, suggesting that suppressing NF-kappa B activation is likely responsible for at least some of the cytotoxicities. One lead compound effectively inhibits lung tumor growth with no signs of adverse side effects.

  DOI：

  10.1021/jm901278z

文献信息

• [EN] NOVEL CDK9 INHIBITOR BASED ON BENZOPYRAN STRUCTURE, PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] NOUVEL INHIBITEUR DE CDK9 À BASE D'UNE STRUCTURE DE BENZOPYRANE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 基于苯并吡喃结构的新型CDK9抑制剂、其制备方法及应用
  申请人：UNIV CHINA PHARMA

  公开号：WO2020228513A1

  公开（公告）日：2020-11-19

  本发明涉及到生物医药领域，具体包括苯并呋喃结构的新型CDK9抑制剂一系列衍生物和其用途；本发明针对汉黄芩素抗肿瘤活性低，成药性差的缺点，对其母核进行改造合成了一系列化合物，特别是针对3'或4'位引入含N环状取代基，该类化合物是全新化合物，未见文献报道，同时发明人针对合成的化合物进行了一系列生物活性评价，具体来说本发明大部分化合物对CDK9具有良好的选择性，并对癌细胞具有较好的抑制活性。
• Structure−Activity Relationship Studies of Chalcone Leading to 3-Hydroxy-4,3′,4′,5′-tetramethoxychalcone and Its Analogues as Potent Nuclear Factor κB Inhibitors and Their Anticancer Activities
  作者：Balasubramanian Srinivasan、Thomas E. Johnson、Rahul Lad、Chengguo Xing

  DOI：10.1021/jm901278z

  日期：2009.11.26

  Chalcone is a privileged structure, demonstrating promising anti-inflammatory and anticancer activities. One potential mechanism is to suppress nuclear factor kappa B (NF-kappa B) activation. The structures of chalcone-based NF-kappa B inhibitors vary significantly that there is minimum information about their structure-activity relationships (SAR). This study aims to establish SAR of chalcone-based compounds to NF-kappa B inhibition, to explore the feasibility of developing simple chalcone-based potent NF-kappa B inhibitors, and to evaluate their anticancer activities. Three series of chalcones were synthesized in one to three steps with the key step being aldol condensation. These candidates demonstrated a wide range of NF-kappa B inhibitory activities, some of low micromolar potency, establishing that structural complexity is not required for NF-kappa B inhibition. Lead compounds also demonstrate potent cytotoxicity against lung cancer cells. Their cytotoxicities correlate moderately well with their NF-kappa B inhibitory activities, suggesting that suppressing NF-kappa B activation is likely responsible for at least some of the cytotoxicities. One lead compound effectively inhibits lung tumor growth with no signs of adverse side effects.