3-oxo-2,3-bis(3,4,5-trimethoxyphenyl)propanenitrile | 1149641-27-9

• 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-oxo-2,3-bis(3,4,5-trimethoxyphenyl)propanenitrile
• CAS: 1149641-27-9
• 化学式: C₂₁H₂₃NO₇
• 分子量: 401.416
• InChiKey: MXUXCDQUKSMHJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-oxo-2,3-bis(3,4,5-trimethoxyphenyl)propanenitrile 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以47%的产率得到3,4-bis(3,4,5-trimethoxyphenyl)isoxazol-5-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of 3,4-diaryl-5-aminoisoxazole derivatives

  摘要：

  A series of cis-restricted 3,4-diaryl-5-aminoisoxazoles have been synthesized and evaluated for their biological activities. Among them, compound 11a and 13a displayed potent cytotoxic activities in vitro against five human cancer cell lines with IC50 values in the low micromolar range and two compounds inhibited tubulin polymerization with IC50 value of 1.8, and 2.1 mu M, respectively, similar to that of CA-4. Compound 13a could arrest at the G2/M phase of the cell cycle at the concentration of 0.1 and 1.0 mu M and induce apoptosis at 0.1-1.0 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.040
• 作为产物：
  描述：

  3,4,5-三甲氧基苯乙腈 、 3,4,5-三甲氧基苯甲酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以68%的产率得到3-oxo-2,3-bis(3,4,5-trimethoxyphenyl)propanenitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of 3,4-diaryl-5-aminoisoxazole derivatives

  摘要：

  A series of cis-restricted 3,4-diaryl-5-aminoisoxazoles have been synthesized and evaluated for their biological activities. Among them, compound 11a and 13a displayed potent cytotoxic activities in vitro against five human cancer cell lines with IC50 values in the low micromolar range and two compounds inhibited tubulin polymerization with IC50 value of 1.8, and 2.1 mu M, respectively, similar to that of CA-4. Compound 13a could arrest at the G2/M phase of the cell cycle at the concentration of 0.1 and 1.0 mu M and induce apoptosis at 0.1-1.0 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.040

文献信息

• 4,5‐Diaryl‐3‐aminopyrazole Derivatives as Analogs of Combretastatin A‐4: Synthesis and Biological Evaluation
  作者：Tao Liu、Rong Cui、Jing Chen、Jun Zhang、Qiaojun He、Bo Yang、Yongzhou Hu

  DOI：10.1002/ardp.201000069

  日期：2011.5

  A series of cis‐restricted 4,5‐diaryl‐3‐aminopyrazole derivatives were synthesized and tested for their cytotoxic activity in vitro against five human cancer cell lines (K562, ECA‐109, A549, SMMC‐7721, and PC‐3). Compounds 5a, 5b, 5d, and 6b showed potent cytotoxicity against all tested cell lines. Primary mechanism research on compound 5a indicated that it was a potent inhibitor of tubulin polymerization, arresting cell cycle in G2/M phase. The docking research showed the conformation of 5a overlaps well with CA‐4 in the crystallized protein complex, suggesting the 4,5‐diaryl‐3‐aminopyrazoles were good mimics of CA‐4.