(benzofuran-2-yl)(3,4,5-trimethoxyphenyl)methanone | 940241-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (benzofuran-2-yl)(3,4,5-trimethoxyphenyl)methanone
• 英文别名: 1-Benzofuran-2-yl-(3,4,5-trimethoxyphenyl)methanone
• CAS: 940241-66-7
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: BPIHCRLYEUYOJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (benzofuran-2-yl)(3,4,5-trimethoxyphenyl)methanone 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 5.42h， 生成 2-[1-(3,4,5-trimethoxyphenyl)vinyl]benzofuran
  参考文献：
  名称：

  Synthesis and biological evaluation of thiophene and benzo[b]thiophene analogs of combretastatin A-4 and isocombretastatin A-4: A comparison between the linkage positions of the 3,4,5-trimethoxystyrene unit

  摘要：

  Combretastatin A-4 and isocombretastatin A-4 derivatives having thiophenes or benzo[b]thiophenes instead of the B ring were prepared and evaluated for their in cellulo tubulin polymerization inhibition (TPI) and antiproliferative activities. The presence of the benzo[b]thiophene ring proved to have a crucial effect as most of the thiophene derivatives, except those having one methoxy group, were inactive to inhibit tubulin polymerization into microtubules. The influence of the attachment position was also studied: benzo[b]thiophenes having iso or cis 3,4,5-trimethoxystyrenes at position 2 were 12-30-fold more active than the 3-regioisomers for the TPI activity. Some of the novel designed compounds exhibited interesting anti-proliferative effects on two different cell lines. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.010
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 6.5h， 生成 (benzofuran-2-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of thiophene and benzo[b]thiophene analogs of combretastatin A-4 and isocombretastatin A-4: A comparison between the linkage positions of the 3,4,5-trimethoxystyrene unit

  摘要：

  Combretastatin A-4 and isocombretastatin A-4 derivatives having thiophenes or benzo[b]thiophenes instead of the B ring were prepared and evaluated for their in cellulo tubulin polymerization inhibition (TPI) and antiproliferative activities. The presence of the benzo[b]thiophene ring proved to have a crucial effect as most of the thiophene derivatives, except those having one methoxy group, were inactive to inhibit tubulin polymerization into microtubules. The influence of the attachment position was also studied: benzo[b]thiophenes having iso or cis 3,4,5-trimethoxystyrenes at position 2 were 12-30-fold more active than the 3-regioisomers for the TPI activity. Some of the novel designed compounds exhibited interesting anti-proliferative effects on two different cell lines. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.010

文献信息

• Design, synthesis and structure–activity relationship of 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b]furan derivatives as a novel class of inhibitors of tubulin polymerization
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Olga Cruz-Lopez、Manlio Tolomeo、Stefania Grimaudo、Antonietta Di Cristina、Maria Rosaria Pipitone、Jan Balzarini、Nicola Zonta、Andrea Brancale、Ernest Hamel

  DOI：10.1016/j.bmc.2009.08.027

  日期：2009.10

  anticancer agents. Small molecules such as benzo[b]furans are attractive as inhibitors of tubulin polymerization. Thus, a new class of inhibitors of tubulin polymerization based on the 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b]furan molecular skeleton, with electron-donating (Me, OMe or OH) or electron-withdrawing (F, Cl and Br) substituents on the benzene ring, was synthesized and evaluated for antiproliferative

  微管在有丝分裂和细胞分裂中的生物学重要性使它们成为开发抗癌剂的有趣目标。苯并[ b ]呋喃等小分子作为微管蛋白聚合的抑制剂很有吸引力。因此，一类新的微管蛋白聚合抑制剂基于 2-(3',4',5'-三甲氧基苯甲酰基)-苯并[ b ]呋喃分子骨架，具有供电子（Me、OMe 或 OH）或电子-去除苯环上的（F、Cl 和 Br）取代基，合成并评估其抗增殖活性、抑制微管蛋白聚合和细胞周期效应。在 C-3 位置添加甲基导致活性增加。该系列中最有前途的化合物是2-(3',4',5'-三甲氧基苯甲酰基)-3-甲基-6-乙氧基-苯并[b ]呋喃，其在纳摩尔浓度下抑制癌细胞生长，并通过与秋水仙碱位点结合而与微管蛋白强烈相互作用。
• Halogen derivatives of benzo[b]furans useful as anti-neoplastic or anti-proliferative drugs
  申请人：Centrum Badan Molekularnych I Makromolekularnych Pan

  公开号：EP2631232B1

  公开（公告）日：2015-09-16