ethyl 4,6-dibenzyloxy-7-carbamoyl-3-methyl-1-benzofuran-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 4,6-dibenzyloxy-7-carbamoyl-3-methyl-1-benzofuran-2-carboxylate
• 英文别名: Ethyl 7-carbamoyl-3-methyl-4,6-bis(phenylmethoxy)-1-benzofuran-2-carboxylate；ethyl 7-carbamoyl-3-methyl-4,6-bis(phenylmethoxy)-1-benzofuran-2-carboxylate
• 化学式: C₂₇H₂₅NO₆
• 分子量: 459.499
• InChiKey: CZNXTQJEBOGJLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-dibenzyloxy-7-carbamoyl-3-methyl-1-benzofuran-2-carboxylate 在 palladium 10% on activated carbon 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以61%的产率得到ethyl 7-carbamoyl-4,6-dihydroxy-3-methyl-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of benzofuran-based analogs of cercosporamide against non-small cell lung cancer cell lines

  摘要：

  A novel series of 3-methyl-1-benzofuran derivatives were synthesized and screened in vitro for their antiproliferative activity against two human NSCLC cell lines (NSCLC-N6 mutant p53 and A549 wild type p53). Most promising compounds presented a structural analogy with the west part of cercosporamide, a natural product of biological interest. In particular, compounds 10, 12 and 31 showed cytotoxic activities at micromolar concentrations (IC50 < 9.3 mu M) and compounds 13, 18 and 32 displayed moderate ICso values (25-40 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.013
• 作为产物：
  描述：

  1,3,5-苯三醇三乙酸酯 在 水 、 四氯化钛 、 sodium hydride 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 47.0h， 生成 ethyl 4,6-dibenzyloxy-7-carbamoyl-3-methyl-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of benzofuran-based analogs of cercosporamide against non-small cell lung cancer cell lines

  摘要：

  A novel series of 3-methyl-1-benzofuran derivatives were synthesized and screened in vitro for their antiproliferative activity against two human NSCLC cell lines (NSCLC-N6 mutant p53 and A549 wild type p53). Most promising compounds presented a structural analogy with the west part of cercosporamide, a natural product of biological interest. In particular, compounds 10, 12 and 31 showed cytotoxic activities at micromolar concentrations (IC50 < 9.3 mu M) and compounds 13, 18 and 32 displayed moderate ICso values (25-40 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.013

文献信息

• Synthesis and antiproliferative activity of benzofuran-based analogs of cercosporamide against non-small cell lung cancer cell lines
  作者：Marc-Antoine Bazin、Lizeth Bodero、Christophe Tomasoni、Bénédicte Rousseau、Christos Roussakis、Pascal Marchand

  DOI：10.1016/j.ejmech.2013.09.013

  日期：2013.11

  A novel series of 3-methyl-1-benzofuran derivatives were synthesized and screened in vitro for their antiproliferative activity against two human NSCLC cell lines (NSCLC-N6 mutant p53 and A549 wild type p53). Most promising compounds presented a structural analogy with the west part of cercosporamide, a natural product of biological interest. In particular, compounds 10, 12 and 31 showed cytotoxic activities at micromolar concentrations (IC50 < 9.3 mu M) and compounds 13, 18 and 32 displayed moderate ICso values (25-40 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.