1,2,3-trimethoxy-5-(2-(4-methoxy-2-nitrophenyl)ethynyl)benzene | 889134-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,3-trimethoxy-5-(2-(4-methoxy-2-nitrophenyl)ethynyl)benzene
• 英文别名: 1,2,3-Trimethoxy-5-[2-(4-methoxy-2-nitrophenyl)ethynyl]benzene
• CAS: 889134-71-8
• 化学式: C₁₈H₁₇NO₆
• 分子量: 343.336
• InChiKey: DZAPGIQSTOWFFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,3-trimethoxy-5-(2-(4-methoxy-2-nitrophenyl)ethynyl)benzene 在 盐酸 、 N-碘代丁二酰亚胺 、 铁粉 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 4.5h， 生成 (7-iodo-6-methoxy-1H-indazol-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Potent Antitubulin Tumor Cell Cytotoxins Based on 3-Aroyl Indazoles

  摘要：

  A series of 3-aroyl indazoles was synthesized. Modification of the C-7 position resulted in a significant structure-activity relationship (SAR) with acetylene modifications conferring unusual potency in a tumor cell cytotoxicity assay. The most potent compounds exceeded the activity of combretastatin A4 (CA-4), showing single digit nM IC50 values against all cell lines tested including those with known efflux resistance pumps. The inhibition of in vitro tubulin polymerization was comparable to CA-4, consistent with tubulin being the target for these compounds. Competition binding experiments employing [H-3]colchicine and purified tubulins demonstrated that the compound specifically binds to the colchicine site.

  DOI：

  10.1021/jm061348t
• 作为产物：
  描述：

  3.4.5-三甲氧基苯乙炔 、 4-碘基-3-硝基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 反应 3.0h， 以88%的产率得到1,2,3-trimethoxy-5-(2-(4-methoxy-2-nitrophenyl)ethynyl)benzene
  参考文献：
  名称：

  WO2006/57946

  摘要：

  公开号：

文献信息

• WO2006/57946
  申请人：——

  公开号：——

  公开（公告）日：——
• Tubulin Binding Anti Cancer Agents And Prodrugs Thereof
  申请人：Matteucci Mark

  公开号：US20090042820A1

  公开（公告）日：2009-02-12

  Novel tubulin binding compounds and hypoxia activated prodrugs of novel and known tubulin binding compounds useful for treating cancer and other hyperproliferative diseases are disclosed.
• Potent Antitubulin Tumor Cell Cytotoxins Based on 3-Aroyl Indazoles
  作者：Jian-Xin Duan、Xiaohong Cai、Fanying Meng、Leslie Lan、Charles Hart、Mark Matteucci

  DOI：10.1021/jm061348t

  日期：2007.3.1

  A series of 3-aroyl indazoles was synthesized. Modification of the C-7 position resulted in a significant structure-activity relationship (SAR) with acetylene modifications conferring unusual potency in a tumor cell cytotoxicity assay. The most potent compounds exceeded the activity of combretastatin A4 (CA-4), showing single digit nM IC50 values against all cell lines tested including those with known efflux resistance pumps. The inhibition of in vitro tubulin polymerization was comparable to CA-4, consistent with tubulin being the target for these compounds. Competition binding experiments employing [H-3]colchicine and purified tubulins demonstrated that the compound specifically binds to the colchicine site.