2-methoxy-5-[(3,4,5-trimethoxyphenyl)sulfanyl]aniline | 1370263-14-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methoxy-5-[(3,4,5-trimethoxyphenyl)sulfanyl]aniline
• 英文别名: 2-Methoxy-5-(3,4,5-trimethoxyphenyl)sulfanylaniline
• CAS: 1370263-14-1
• 化学式: C₁₆H₁₉NO₄S
• 分子量: 321.397
• InChiKey: HKGFOPRPIQQGQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-硝基苯甲醚 在 盐酸 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 新铜试剂 、 tin(II) chloride dihdyrate 、 硫酸 、 sodium t-butanolate 作用下， 以 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 31.33h， 生成 2-methoxy-5-[(3,4,5-trimethoxyphenyl)sulfanyl]aniline
  参考文献：
  名称：

  Synthesis and evaluation of diaryl sulfides and diaryl selenide compounds for antitubulin and cytotoxic activity

  摘要：

  We have devised a procedure for the synthesis of analogs of combretastatin A-4 (CA-4) containing sulfur and selenium atoms as spacer groups between the aromatic rings. CA-4 is well known for its potent activity as an inhibitor of tubulin polymerization, and its prodrugs combretastatin A-4 phosphate (CA-4P) and combretastatin A-1 phosphate (CA-1P) are being investigated as antitumor agents that cause tumor vascular collapse in addition to their activity as cytotoxic compounds. Here we report the preparation of two sulfur analogs and one selenium analog of CA-4. All synthesized compounds, as well as several synthetic intermediates, were evaluated for inhibition of tubulin polymerization and for cytotoxic activity in human cancer cells. Compounds 3 and 4 were active at nM concentration against MCF-7 breast cancer cells. As inhibitors of tubulin polymerization, both 3 and 4 were more active than CA-4 itself. In addition, 4 was the most active of these agents against 786, HT-29 and PC-3 cancer cells. Molecular modeling binding studies are also reported for compounds 1, 3, 4 and CA-4 to tubulin within the colchicine site. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.009

文献信息

• Synthesis and evaluation of diaryl sulfides and diaryl selenide compounds for antitubulin and cytotoxic activity
  作者：Edson dos A. dos Santos、Ernest Hamel、Ruoli Bai、James C. Burnett、Camila Santos Suniga Tozatti、Danielle Bogo、Renata T. Perdomo、Alexandra M.M. Antunes、M. Matilde Marques、Maria de F.C. Matos、Dênis P. de Lima

  DOI：10.1016/j.bmcl.2013.06.009

  日期：2013.8

  We have devised a procedure for the synthesis of analogs of combretastatin A-4 (CA-4) containing sulfur and selenium atoms as spacer groups between the aromatic rings. CA-4 is well known for its potent activity as an inhibitor of tubulin polymerization, and its prodrugs combretastatin A-4 phosphate (CA-4P) and combretastatin A-1 phosphate (CA-1P) are being investigated as antitumor agents that cause tumor vascular collapse in addition to their activity as cytotoxic compounds. Here we report the preparation of two sulfur analogs and one selenium analog of CA-4. All synthesized compounds, as well as several synthetic intermediates, were evaluated for inhibition of tubulin polymerization and for cytotoxic activity in human cancer cells. Compounds 3 and 4 were active at nM concentration against MCF-7 breast cancer cells. As inhibitors of tubulin polymerization, both 3 and 4 were more active than CA-4 itself. In addition, 4 was the most active of these agents against 786, HT-29 and PC-3 cancer cells. Molecular modeling binding studies are also reported for compounds 1, 3, 4 and CA-4 to tubulin within the colchicine site. (C) 2013 Elsevier Ltd. All rights reserved.