(E)-3-(2-chlorophenyl)-1-(2,5-dihydroxyphenyl)prop-2-en-1-one | 108718-97-4

• 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-(2-chlorophenyl)-1-(2,5-dihydroxyphenyl)prop-2-en-1-one
• 英文别名: 2-Chlor-2',5'-dihydroxy-chalkon
• CAS: 108718-97-4
• 化学式: C₁₅H₁₁ClO₃
• 分子量: 274.704
• InChiKey: ZRJCUTVXCOCBJS-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 barium dihydroxide 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (E)-3-(2-chlorophenyl)-1-(2,5-dihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Cytotoxic 2′,5′-dihydroxychalcones with unexpected antiangiogenic activity

  摘要：

  A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups ere less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds. 2-chloro-2'.5'dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT 116 cells. This Compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day (-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01443-5

文献信息

• Synthesis, antioxidant, <i>in silico</i> and computational investigation of 2,5-dihydroxyacetophenone derived chloro-substituted hydroxychalcones, hydroxyflavanones and hydroxyflavindogenides
  作者：Aysha Siddiqa、Affifa Tajammal、Ahmad Irfan、Munawar Ali Munawar、Muhammad Azam、Muhammad Asim Raza Basra

  DOI：10.1080/07391102.2021.1943527

  日期：2022.11.29

  An imbalance between reactive oxygen species (ROS) and their elimination by antioxidants damages the cell and infect whole organism. The biological defence system against oxidative stress injury is Kelch-like ECH associated protein 1 (Keap1)-nuclear factor erythroid 2-related factor 2 (Nrf2)-antioxidant response elements (ARE) pathways. Antioxidants activate the Nrf2-ARE-Keap1 pathway and suppress the oxidative stress. Flavonoids are well known medicinal compounds inheriting antioxidant efficacy and wide spectrum of pharmacological activities. The study is aimed to synthesise, characterize and evaluate pharmacological activities of synthesized chloro-derivatives of flavonoids. Chloro-derivatives of flavonoids were synthesized and characterized by IR, 1H NMR and 13C NMR. Antioxidant potential of each synthesized compound was evaluated and then subjected to molecular docking with Keap1 (PDB ID: 2FLU) for the activation of Nrf2 and computational studies were performed by using DFT approach. Among the synthesized compounds compound 1a exhibited lower IC50 value. While docking and computational studies infer that compound 3c is a good Nrf2 activator and radical scavenger with highest docking score and lower energy gaps and IP values compared to references. Hence, it might be considered for further molecular studies for the treatment of inflammatory diseases through Nrf2-ARE-Keap1 pathway.Communicated by Ramaswamy H. Sarma.HighlightsChloro-substituted hydroxychalcones, hydroxyflavanones and hydroxyflavindogenides were synthesized.Antioxidant potential was accessed, compound 1a exhibited good antioxidant potential.In silico study was performed with Keap1, compound 3c have shown highest docking score with Keap1.DFT approach was used to explore the structure activity relationship.
• Cytotoxic 2′,5′-dihydroxychalcones with unexpected antiangiogenic activity
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0223-5234(02)01443-5

  日期：2003.2

  A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups ere less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds. 2-chloro-2'.5'dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT 116 cells. This Compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day (-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.