1-(3-苯氧基苯基)-2-苯基乙烷-1,2-二酮 | 1294481-64-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(3-苯氧基苯基)-2-苯基乙烷-1,2-二酮
• 英文名称: 1-(3-phenoxyphenyl)-2-phenylethane-1,2-dione
• 英文别名: 3-Phenoxybenzil
• CAS: 1294481-64-3
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: OVHBDEBRVLCKMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-苯氧基苯基)-2-苯基乙烷-1,2-二酮 、 1-环己基-2-硫脲 在 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Evaluation of Aminohydantoins as a Novel Class of Antimalarial Agents

  摘要：

  Given the threat of drug resistance, there is an acute need for new classes of antimalarial agents that act via a unique mechanism of action relative to currently used drugs. We have identified a set of druglike compounds within the Tres Cantos Anti-Malarial Set (TCAMS) which likely act via inhibition of a Plasmodium aspartic protease. Structure-activity relationship analysis and optimization of these aminohydantoins demonstrate that these compounds are potent nanomolar inhibitors of the Plasmodium aspartic proteases PM-II and PM-IV and likely one or more other Plasmodium aspartic proteases. Incorporation of a bulky group, such as a cyclohexyl group, on the aminohydantion N-3 position gives enhanced antimalarial potency while reducing inhibition of human aspartic proteases such as BACE. We have identified compound 8p (CWHM-117) as a promising lead for optimization as an antimalarial drug with a low molecular weight, modest lipophilicity, oral bioavailability, and in vivo antimalarial activity in mice.

  DOI：

  10.1021/ml400412x
• 作为产物：
  描述：

  1-phenoxy-3-(2-phenylethenyl)benzene 在 叔丁基过氧化氢 、 (p-cymene)ruthenium(II) chloride 、 Tributyl-pentyl-ammoniumiodid 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 1.0h， 以73%的产率得到1-(3-苯氧基苯基)-2-苯基乙烷-1,2-二酮
  参考文献：
  名称：

  钌在室温下催化烯烃的氧化：一种简便实用的α-二酮方法

  摘要：

  烯烃催化氧化为α-二酮是前所未有的。描述了一种新的由钌配合物催化的烯烃氧化，可使用TBHP作为氧化剂有效地合成α-二酮。该方法具有高度的官能团耐受性，实用方便，不需要额外的配体，并且可在温和条件下以较短的反应时间运行。基于实验观察，提出了一个合理的机制。

  DOI：

  10.1021/ol200716d

文献信息

• US4108835A
  申请人：——

  公开号：US4108835A

  公开（公告）日：1978-08-22
• US4131748A
  申请人：——

  公开号：US4131748A

  公开（公告）日：1978-12-26
• Ruthenium-Catalyzed Oxidation of Alkenes at Room Temperature: A Practical and Concise Approach to α-Diketones
  作者：Shulin Chen、Zhaojun Liu、Erbo Shi、Long Chen、Wei Wei、Hong Li、Yannan Cheng、Xiaobing Wan

  DOI：10.1021/ol200716d

  日期：2011.5.6

  The catalytic oxidation of alkenes to α-diketones is unprecedented. A new oxidation of alkenes, catalyzed by a ruthenium complex, which allows an efficient route to α-diketones using TBHP as an oxidant is described. This methodology is highly functional group tolerant, is practically convenient, requires no additional ligand, and operates under mild conditions with short reaction times. Based upon

  烯烃催化氧化为α-二酮是前所未有的。描述了一种新的由钌配合物催化的烯烃氧化，可使用TBHP作为氧化剂有效地合成α-二酮。该方法具有高度的官能团耐受性，实用方便，不需要额外的配体，并且可在温和条件下以较短的反应时间运行。基于实验观察，提出了一个合理的机制。
• Evaluation of Aminohydantoins as a Novel Class of Antimalarial Agents
  作者：Marvin J. Meyers、Micky D. Tortorella、Jing Xu、Limei Qin、Zhengxiang He、Xingfen Lang、Wentian Zeng、Wanwan Xu、Li Qin、Michael J. Prinsen、Francis M. Sverdrup、Christopher S. Eickhoff、David W. Griggs、Jonathan Oliva、Peter G. Ruminski、E. Jon Jacobsen、Mary A. Campbell、David C. Wood、Daniel E. Goldberg、Xiaorong Liu、Yongzhi Lu、Xin Lu、Zhengchao Tu、Xiaoyun Lu、Ke Ding、Xiaoping Chen

  DOI：10.1021/ml400412x

  日期：2014.1.9

  Given the threat of drug resistance, there is an acute need for new classes of antimalarial agents that act via a unique mechanism of action relative to currently used drugs. We have identified a set of druglike compounds within the Tres Cantos Anti-Malarial Set (TCAMS) which likely act via inhibition of a Plasmodium aspartic protease. Structure-activity relationship analysis and optimization of these aminohydantoins demonstrate that these compounds are potent nanomolar inhibitors of the Plasmodium aspartic proteases PM-II and PM-IV and likely one or more other Plasmodium aspartic proteases. Incorporation of a bulky group, such as a cyclohexyl group, on the aminohydantion N-3 position gives enhanced antimalarial potency while reducing inhibition of human aspartic proteases such as BACE. We have identified compound 8p (CWHM-117) as a promising lead for optimization as an antimalarial drug with a low molecular weight, modest lipophilicity, oral bioavailability, and in vivo antimalarial activity in mice.