5-methyl-2-oxo-5-vinylcyclohex-3-enecarbonitrile | 1207110-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methyl-2-oxo-5-vinylcyclohex-3-enecarbonitrile
• 英文别名: 5-Ethenyl-5-methyl-2-oxocyclohex-3-ene-1-carbonitrile
• CAS: 1207110-05-1
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: XZMXYPNPCBKNCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-2-oxo-5-vinylcyclohex-3-enecarbonitrile 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 0.33h， 以61%的产率得到3-methyl-6-oxo-3-vinyl-cyclohexa-1,4-dienecarbonitrile
  参考文献：
  名称：

  [EN] MONOCYCLIC CYANOENONES AND METHODS OF USE THEREOF
  [FR] CYANOÉNONES MONOCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  本发明涉及单环氰基烯酮组合物及其在治疗癌症、炎症性疾病和神经退行性疾病等疾病中的应用方法。

  公开号：

  WO2010011782A1
• 作为产物：
  描述：

  5-methyl-5-vinyl-4,5-dihydro-benzo[d]isoxazole 在 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 以96%的产率得到5-methyl-2-oxo-5-vinylcyclohex-3-enecarbonitrile
  参考文献：
  名称：

  [EN] MONOCYCLIC CYANOENONES AND METHODS OF USE THEREOF
  [FR] CYANOÉNONES MONOCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  本发明涉及单环氰基烯酮组合物及其在治疗癌症、炎症性疾病和神经退行性疾病等疾病中的应用方法。

  公开号：

  WO2010011782A1

文献信息

• [EN] MONOCYCLIC CYANOENONES AND METHODS OF USE THEREOF<br/>[FR] CYANOÉNONES MONOCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：DARTMOUTH COLLEGE

  公开号：WO2010011782A1

  公开（公告）日：2010-01-28

  The present invention features monocyclic cyanoenone compositions and methods for using the same in the treatment of diseases such as cancer, inflammatory diseases and neurodegenerative diseases.

  本发明涉及单环氰基烯酮组合物及其在治疗癌症、炎症性疾病和神经退行性疾病等疾病中的应用方法。
• MONOCYCLIC CYANOENONES AND METHODS OF USE THEREOF
  申请人：Honda Tadashi

  公开号：US20110196007A1

  公开（公告）日：2011-08-11

  The present invention features monocyclic cyanoenone compositions and methods for using the same in the treatment of diseases such as cancer, inflammatory diseases and neurodegenerative diseases.

  本发明涉及单环氰基烯酮组合物及其在治疗癌症、炎症性疾病和神经退行性疾病等疾病中的应用方法。
• US8314137B2
  申请人：——

  公开号：US8314137B2

  公开（公告）日：2012-11-20
• US9000188B2
  申请人：——

  公开号：US9000188B2

  公开（公告）日：2015-04-07
• Synthesis, Chemical Reactivity as Michael Acceptors, and Biological Potency of Monocyclic Cyanoenones, Novel and Highly Potent Anti-inflammatory and Cytoprotective Agents
  作者：Suqing Zheng、Y. R. Santosh Laxmi、Emilie David、Albena T. Dinkova-Kostova、Katherine H. Shiavoni、Yanqing Ren、Ying Zheng、Isaac Trevino、Ronald Bumeister、Iwao Ojima、W. Christian Wigley、James B. Bliska、Dale F. Mierke、Tadashi Honda

  DOI：10.1021/jm3003922

  日期：2012.5.24

  Novel monocyclic cyanoenones examined to date display unique features regarding chemical reactivity as Michael acceptors and biological potency. Remarkably, in some biological assays, the simple structure is more potent than pentacyclic triterpenoids (e.g., CDDO and bardoxolone methyl) and tricycles (e.g., TBE-31). Among monocyclic cyanoenones, 1 is a highly reactive Michael acceptor with thiol nucleophiles. Furthermore, an important feature of 1 is that its Michael addition is reversible. For the inhibition of NO production, 1 shows the highest potency. Notably, its potency is about three times higher than CDDO, whose methyl ester (bardoxolone methyl) is presently in phase III clinical trials. For the induction of NQO1, 1 also demonstrated the highest potency. These results suggest that the reactivity of these Michael acceptors is closely related to their biological potency. Interestingly, in LPS-stimulated macrophages, 1 causes apoptosis and inhibits secretion of TNF-alpha and IL-1 beta with potencies that are higher than those of bardoxolone methyl and TBE-31.