(E)-1-(5-ethoxy-2-hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one | 1067559-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-1-(5-ethoxy-2-hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one
• CAS: 1067559-63-0
• 化学式: C₁₆H₁₆O₃S
• 分子量: 288.367
• InChiKey: JASPOJIPHLZFGI-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-1-(2,5-dihydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one 、 碘乙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以89%的产率得到(E)-1-(5-ethoxy-2-hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2′,5′-dialkoxylchalcones as cancer chemopreventive agents

  摘要：

  In an effort to develop novel anti-tumor, or cancer chemopreventive agents, a series of 2',5'-dialkoxylchalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with suitable aromatic aldehyde. In vitro screening revealed low micromolar activity (IC50) against several human cancer cell lines. Selective compound 10 induced an accumulation of A549 cells in the G(2)/M phase arrest which was well correlated with inhibitory activity against tubulin polymerization. Cytotoxic compounds 3 and 12 showed significant inhibitory effects on NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophage-like cells while cytotoxic compound 10 revealed potent inhibitory effect on TNF-alpha formation in RAW 264.7 cells in response to LPS. Compounds 3 and 10 also showed significant inhibitory effects on xanthine oxidase. The present results suggested that compounds 3 and 10 were potential to be served as cancer chemopreventive agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.031

文献信息

• Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2′,5′-dialkoxylchalcones as cancer chemopreventive agents
  作者：Jen-Hao Cheng、Chi-Feng Hung、Shyh-Chyun Yang、Jih-Pyang Wang、Shen-Jeu Won、Chun-Nan Lin

  DOI：10.1016/j.bmc.2008.06.031

  日期：2008.8

  In an effort to develop novel anti-tumor, or cancer chemopreventive agents, a series of 2',5'-dialkoxylchalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with suitable aromatic aldehyde. In vitro screening revealed low micromolar activity (IC50) against several human cancer cell lines. Selective compound 10 induced an accumulation of A549 cells in the G(2)/M phase arrest which was well correlated with inhibitory activity against tubulin polymerization. Cytotoxic compounds 3 and 12 showed significant inhibitory effects on NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophage-like cells while cytotoxic compound 10 revealed potent inhibitory effect on TNF-alpha formation in RAW 264.7 cells in response to LPS. Compounds 3 and 10 also showed significant inhibitory effects on xanthine oxidase. The present results suggested that compounds 3 and 10 were potential to be served as cancer chemopreventive agents. (C) 2008 Elsevier Ltd. All rights reserved.