(Z)-methyl 3-(2-chloro-3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylate | 1453904-39-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-methyl 3-(2-chloro-3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylate
• 英文别名: methyl (Z)-3-(2-chloro-3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)prop-2-enoate
• CAS: 1453904-39-6
• 化学式: C₁₆H₁₃ClO₅
• 分子量: 320.729
• InChiKey: QLGRLGVUNSOCNK-QPEQYQDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-methyl 3-(2-chloro-3,5-diisopropoxyphenyl)-2-(4-methoxyphenyl)acrylate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以10%的产率得到(Z)-methyl 3-(2-chloro-3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylate
  参考文献：
  名称：

  Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2

  摘要：

  Resveratrol (3,5,4'-trihydroxylstilbene) has been proposed to elicit a variety of positive health effects including protection against cancer and cardiovascular disease. The highest affinity target of resveratrol identified so far is the oxidoreductase enzyme quinone reductase 2 (QR2), which is believed to function in metabolic reduction and detoxification processes; however, evidence exists linking QR2 to the metabolic activation of quinones, which can lead to cell toxicity. Therefore, inhibition of QR2 by resveratrol may protect cells against reactive intermediates and eventually cancer. With the aim of identifying novel inhibitors of QR2, we designed, synthesized, and tested two generations of resveratrol analogue libraries for inhibition of QR2. In addition, Xray crystal structures of six of the resveratrol analogues in the active site of QR2 were determined. Several novel inhibitors of QR2 were successfully identified as well as a compound that inhibits QR2 with a novel binding orientation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.037

文献信息

• Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2
  作者：Sarah E. St. John、Katherine C. Jensen、SooSung Kang、Yafang Chen、Barbara Calamini、Andrew D. Mesecar、Mark A. Lipton

  DOI：10.1016/j.bmc.2013.07.037

  日期：2013.10

  Resveratrol (3,5,4'-trihydroxylstilbene) has been proposed to elicit a variety of positive health effects including protection against cancer and cardiovascular disease. The highest affinity target of resveratrol identified so far is the oxidoreductase enzyme quinone reductase 2 (QR2), which is believed to function in metabolic reduction and detoxification processes; however, evidence exists linking QR2 to the metabolic activation of quinones, which can lead to cell toxicity. Therefore, inhibition of QR2 by resveratrol may protect cells against reactive intermediates and eventually cancer. With the aim of identifying novel inhibitors of QR2, we designed, synthesized, and tested two generations of resveratrol analogue libraries for inhibition of QR2. In addition, Xray crystal structures of six of the resveratrol analogues in the active site of QR2 were determined. Several novel inhibitors of QR2 were successfully identified as well as a compound that inhibits QR2 with a novel binding orientation. (c) 2013 Elsevier Ltd. All rights reserved.