(Z)-tert-butyl(2-methoxy-5-(3-nitrostyryl)phenoxy)dimethylsilane | 936103-92-3

• 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)-tert-butyl(2-methoxy-5-(3-nitrostyryl)phenoxy)dimethylsilane
• CAS: 936103-92-3
• 化学式: C₂₁H₂₇NO₄Si
• 分子量: 385.535
• InChiKey: VSRFDMBRAJCHOX-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-tert-butyl(2-methoxy-5-(3-nitrostyryl)phenoxy)dimethylsilane 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、262.01 kPa 条件下， 反应 40.0h， 生成 1-(2-Chloroethyl)-3-[3-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenyl]urea
  参考文献：
  名称：

  N-Phenyl-N′-(2-chloroethyl)urea analogues of combretastatin A-4: Is the N-phenyl-N′-(2-chloroethyl)urea pharmacophore mimicking the trimethoxy phenyl moiety?

  摘要：

  A series of novel N-phe.rlyl-N'-(2-chloroethyl)urea derivatives potentially mimicking the structure of combretastatin A-4 were synthesized and tested for their cell growth inhibition and their binding to the colchicine-binding site of beta-tubulin. Compounds 2a, 3a, and 3b were found to inhibit cell growth at the micromolar level on four human tumor cell lines. Flow cytometric analysis indicates that the new compounds act as antimitotics and arrest the cell cycle in G(2)/M phase. Covalent binding of 2a, 3a, and 3b to the colchicine-binding site of beta-tubulin was confirmed also using SDS-PAGE and competition assays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.023
• 作为产物：
  描述：

  3-硝基溴苄 在 sodium hydride 作用下， 以 二氯甲烷 、 间二甲苯 为溶剂， 反应 32.0h， 生成 (Z)-tert-butyl(2-methoxy-5-(3-nitrostyryl)phenoxy)dimethylsilane
  参考文献：
  名称：

  N-Phenyl-N′-(2-chloroethyl)urea analogues of combretastatin A-4: Is the N-phenyl-N′-(2-chloroethyl)urea pharmacophore mimicking the trimethoxy phenyl moiety?

  摘要：

  A series of novel N-phe.rlyl-N'-(2-chloroethyl)urea derivatives potentially mimicking the structure of combretastatin A-4 were synthesized and tested for their cell growth inhibition and their binding to the colchicine-binding site of beta-tubulin. Compounds 2a, 3a, and 3b were found to inhibit cell growth at the micromolar level on four human tumor cell lines. Flow cytometric analysis indicates that the new compounds act as antimitotics and arrest the cell cycle in G(2)/M phase. Covalent binding of 2a, 3a, and 3b to the colchicine-binding site of beta-tubulin was confirmed also using SDS-PAGE and competition assays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.023