(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile

• 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)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile
• 英文别名: (Z)-3-(3,5-Dimethoxy-phenyl)-2-(4-methoxy-phenyl)-acrylonitrile；(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-enenitrile
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: BZZNWCSTGMTJMR-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile 在 乙醛肟 、 palladium diacetate 、 三苯基膦 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以92%的产率得到(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylamide
  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
• 作为产物：
  描述：

  4-甲氧基苄醇 在 四溴化碳 、 三苯基膦 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.83h， 生成 (Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile
  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

• Enzyme-mediated oxidative dimerization reactions of cyano-resveratrol analogues
  作者：Zhibo Shao、Xiaodong Kang、Hongpeng Li、Lu Ran、Wenling Li

  DOI：10.1016/j.tetlet.2019.151275

  日期：2019.11

  The synthesis and oxidative coupling reactions of two cyano-resveratrol analogues were studied. An 8-5-coupled dihydrobenzofuran-type dimer and an 8-8-coupled diastereoisomeric indane mixture were prepared. The cyano groups of the resveratrol analogues had almost no influence on the regio- or stereoselectivity of the coupling reactions of the two precursors.

  研究了两种氰基-白藜芦醇类似物的合成和氧化偶联反应。制备了8-5偶合的二氢苯并呋喃型二聚体和8-8偶合的非对映异构体的茚满混合物。白藜芦醇类似物的氰基几乎不影响两种前体偶联反应的区域选择性或立体选择性。
• Discovery of Diarylacrylonitriles as a Novel Series of Small Molecule Sortase A Inhibitors
  作者：Ki-Bong Oh、Soo-Hwan Kim、Jaekwang Lee、Won-Jea Cho、Taeho Lee、Sanghee Kim

  DOI：10.1021/jm0498708

  日期：2004.5.1

  On the basis of a hit from random screening, a novel class of small-molecule sortase A inhibitors was generated. The primary structure-activity relationship and the minimal structural requirements for potency were established through structural modifications and molecular modeling studies.