4-methoxy-benzofuran-6-yl-methyl-triphenyl-phosphonium bromide | 831223-02-0

• 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: 4-methoxy-benzofuran-6-yl-methyl-triphenyl-phosphonium bromide
• 英文别名: [(4-Methoxy-1-benzofuran-6-yl)methyl](triphenyl)phosphanium bromide；(4-methoxy-1-benzofuran-6-yl)methyl-triphenylphosphanium;bromide
• CAS: 831223-02-0
• 化学式: Br*C₂₈H₂₄O₂P
• 分子量: 503.375
• InChiKey: LZWXDJXLMUOKLP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-benzofuran-6-yl-methyl-triphenyl-phosphonium bromide 、 3-叔-丁基二甲基硅氧基-4-甲氧基苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Novel A-Ring and B-Ring Modified Combretastatin A-4 (CA-4) Analogues Endowed with Interesting Cytotoxic Activity

  摘要：

  A novel class of combretastatins, modified at A-ring or both A- and B-rings, mainly by replacement with benzofuran or benzo[b]thiophene, were synthesized. The new heterocombretastatins showed good cytotoxic activity on BMEC and H-460 cell lines. The aminocombretastatin 9f potently inhibits cell growth of BMEC and combretastatin-resistant HT-29 cell lines, with potential interest to treat colon carcinoma. Heterocombretastatins 9a,b inhibit tubulin polymerization similarly to CA-4 by having a binding to colchicine site five times stronger.

  DOI：

  10.1021/jm8005004
• 作为产物：
  描述：

  6-bromomethyl-4-methoxy-benzofuran 在 三苯基膦 作用下， 以 xylene 为溶剂， 反应 12.0h， 以83%的产率得到4-methoxy-benzofuran-6-yl-methyl-triphenyl-phosphonium bromide
  参考文献：
  名称：

  [EN] COMBRETASTATIN DERIVATIVES WITH CYTOTOXIC ACTION
  [FR] DERIVES DE LA COMBRETASTATINE A ACTION CYTOTOXIQUE

  摘要：

  公开号：

  WO2005007635A3

文献信息

• [EN] COMBRETASTATIN DERIVATIVES WITH CYTOTOXIC ACTION<br/>[FR] DERIVES DE LA COMBRETASTATINE A ACTION CYTOTOXIQUE
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2005007635A3

  公开（公告）日：2005-08-11
• Novel A-Ring and B-Ring Modified Combretastatin A-4 (CA-4) Analogues Endowed with Interesting Cytotoxic Activity
  作者：Daniele Simoni、Romeo Romagnoli、Riccardo Baruchello、Riccardo Rondanin、Giuseppina Grisolia、Marco Eleopra、Michele Rizzi、Manlio Tolomeo、Giuseppe Giannini、Domenico Alloatti、Massimo Castorina、Marcella Marcellini、Claudio Pisano

  DOI：10.1021/jm8005004

  日期：2008.10.9

  A novel class of combretastatins, modified at A-ring or both A- and B-rings, mainly by replacement with benzofuran or benzo[b]thiophene, were synthesized. The new heterocombretastatins showed good cytotoxic activity on BMEC and H-460 cell lines. The aminocombretastatin 9f potently inhibits cell growth of BMEC and combretastatin-resistant HT-29 cell lines, with potential interest to treat colon carcinoma. Heterocombretastatins 9a,b inhibit tubulin polymerization similarly to CA-4 by having a binding to colchicine site five times stronger.