3-(Dimethylamino)-1-(5-ethyl-4-methoxy-2-phenylmethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-one | 1271727-99-1

• 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: 3-(Dimethylamino)-1-(5-ethyl-4-methoxy-2-phenylmethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 3-(dimethylamino)-1-(5-ethyl-4-methoxy-2-phenylmethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1271727-99-1
• 化学式: C₂₈H₃₁NO₄
• 分子量: 445.558
• InChiKey: RQNIHWIQMAIYOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(Dimethylamino)-1-(5-ethyl-4-methoxy-2-phenylmethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-one 在 盐酸羟胺 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到5-(2-benzyloxy-5-ethyl-4-methoxyphenyl)-4-(4-methoxyphenyl)isoxazole
  参考文献：
  名称：

  Convenient Synthesis of an Isoxazole Compound, KRIBB3, as an Anticancer Agent

  摘要：

  A diaryl isoxazole compound, KRIBB3, which exhibits strong antimigratory and antimitotic activities against cancer cells, was prepared in a practical synthetic way. The synthetic method may provide easy access to KRIBB3 analogs with various substituents at an aryl moiety for structure-activity relationships (SAR), as well as a large quantity of KRIBB3 for in vivo studies.

  DOI：

  10.1080/00397911.2010.546551
• 作为产物：
  描述：

  5-ethyl-2,4-dihydroxy-benzaldehyde 在 四丙基高钌酸铵 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.5h， 生成 3-(Dimethylamino)-1-(5-ethyl-4-methoxy-2-phenylmethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Convenient Synthesis of an Isoxazole Compound, KRIBB3, as an Anticancer Agent

  摘要：

  A diaryl isoxazole compound, KRIBB3, which exhibits strong antimigratory and antimitotic activities against cancer cells, was prepared in a practical synthetic way. The synthetic method may provide easy access to KRIBB3 analogs with various substituents at an aryl moiety for structure-activity relationships (SAR), as well as a large quantity of KRIBB3 for in vivo studies.

  DOI：

  10.1080/00397911.2010.546551

文献信息

• Biological evaluation of KRIBB3 analogs as a microtubule polymerization inhibitor
  作者：Sangku Lee、Jae Nyoung Kim、Hyeong Kyu Lee、Kab Seog Yoon、Ki Deok Shin、Byoung-Mog Kwon、Dong Cho Han

  DOI：10.1016/j.bmcl.2010.12.044

  日期：2011.2

  A series of KRIBB3 analogs were synthesized by modifying substituents at aryl moieties of KRIBB3 for examining structure-activity relationships, and their inhibitory activities on microtubule polymerization were evaluated. The presence of free phenolic hydrogens in aryl moieties of KRIBB3 analogs plays an important role in inhibition of microtubule polymerization. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of KRIBB3 Analogues on a Proliferation of HCT-116 Colorectal Cancer Cells
  作者：Sang-Ku Lee、Jae-Nyoung Kim、Ji-Hye Min、Kab-Seog Yoon、Ki-Deok Shin、Byoung-Mog Kwon、Dong-Cho Han

  DOI：10.5012/bkcs.2010.31.12.3800

  日期：2010.12.20
• Convenient Synthesis of an Isoxazole Compound, KRIBB3, as an Anticancer Agent
  作者：Hyeong Kyu Lee、Eunju Yun、Ji Hye Min、Kab Seog Yoon、Dong-Ho Choung、Sangku Lee

  DOI：10.1080/00397911.2010.546551

  日期：2012.7.1

  A diaryl isoxazole compound, KRIBB3, which exhibits strong antimigratory and antimitotic activities against cancer cells, was prepared in a practical synthetic way. The synthetic method may provide easy access to KRIBB3 analogs with various substituents at an aryl moiety for structure-activity relationships (SAR), as well as a large quantity of KRIBB3 for in vivo studies.