(2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(2,5-dimethoxyphenyl)prop-2-en-1-one) | 1357167-63-5

• 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: (2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(2,5-dimethoxyphenyl)prop-2-en-1-one)
• 英文别名: (E)-3-(2,5-dimethoxyphenyl)-1-[5-[(E)-3-(2,5-dimethoxyphenyl)prop-2-enoyl]-2,4-dihydroxyphenyl]prop-2-en-1-one
• CAS: 1357167-63-5
• 化学式: C₂₈H₂₆O₈
• 分子量: 490.51
• InChiKey: KJRRZTWGKVNIKR-NXZHAISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  间苯二酚 在 盐酸 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 (2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(2,5-dimethoxyphenyl)prop-2-en-1-one)
  参考文献：
  名称：

  Bis-chalcone analogues as potent NO production inhibitors and as cytotoxic agents

  摘要：

  Chalcones have a distinctive 1,3-diarylpropenone skeleton and exert numerous biological effects. Using a one-step Claisen-Schmidt condensation, we synthesized eleven bis-chalcones (3-13) and three acetyl chalcones (14-16) from substituted aldehydes and diacetylresorcinol. The compounds were tested for in vitro cytotoxic activity against four human cancer cell lines (A549, DU145, KB, and KB-VIN) and inhibition of NO production in lipopolysaccharide (LPS)-activated microglial cells. Among them, four compounds (3, 5, 6, and 13) showed significant cytotoxic activity with EC50 values ranging from 1.57 to 514 mu M, and seven compounds (3, 5-8, 10, and 13) displayed potent anti-inflammatory activity by inhibiting NO production with IC50 values ranging from 0.95 to 8.65 mu M. A mechanism of action study of active compounds 6 and 7 discovered that these compounds down-regulated iNOS expression by inhibiting p65 NF-kappa B activation/nuclear translocation due to prevention of ham degradation. Structure-activity relationship (SAR) findings are also discussed. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.026

文献信息

• Bis-chalcone analogues as potent NO production inhibitors and as cytotoxic agents
  作者：M. Vijaya Bhaskar Reddy、Yuh-Chiang Shen、Emika Ohkoshi、Kenneth F. Bastow、Keduo Qian、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.ejmech.2011.10.026

  日期：2012.1

  Chalcones have a distinctive 1,3-diarylpropenone skeleton and exert numerous biological effects. Using a one-step Claisen-Schmidt condensation, we synthesized eleven bis-chalcones (3-13) and three acetyl chalcones (14-16) from substituted aldehydes and diacetylresorcinol. The compounds were tested for in vitro cytotoxic activity against four human cancer cell lines (A549, DU145, KB, and KB-VIN) and inhibition of NO production in lipopolysaccharide (LPS)-activated microglial cells. Among them, four compounds (3, 5, 6, and 13) showed significant cytotoxic activity with EC50 values ranging from 1.57 to 514 mu M, and seven compounds (3, 5-8, 10, and 13) displayed potent anti-inflammatory activity by inhibiting NO production with IC50 values ranging from 0.95 to 8.65 mu M. A mechanism of action study of active compounds 6 and 7 discovered that these compounds down-regulated iNOS expression by inhibiting p65 NF-kappa B activation/nuclear translocation due to prevention of ham degradation. Structure-activity relationship (SAR) findings are also discussed. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.