ethyl (2S,3S)-3-[(4-bromophenyl)methylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate | 958424-44-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2S,3S)-3-[(4-bromophenyl)methylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate
• CAS: 958424-44-7
• 化学式: C₂₂H₂₆BrNO₆
• 分子量: 480.356
• InChiKey: ITHYOOWLVALTNV-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3S)-3-[(4-bromophenyl)methylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate 、 氯甲酸烯丙酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到ethyl (2S,3S)-3-[(4-bromophenyl)methyl-prop-2-enoxycarbonylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  Benzofuran-Derived Cyclic β-Amino Acid Scaffold for Building a Diverse Set of Flavonoid-Like Probes and the Discovery of a Cell Motility Inhibitor

  摘要：

  We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC(50) approximate to 40 mu M in chamber cell migration assay).

  DOI：

  10.1021/ol800050g
• 作为产物：
  描述：

  ethyl (2S,3S)-3-amino-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate 、 对溴溴苄 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以60%的产率得到ethyl (2S,3S)-3-[(4-bromophenyl)methylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  Benzofuran-Derived Cyclic β-Amino Acid Scaffold for Building a Diverse Set of Flavonoid-Like Probes and the Discovery of a Cell Motility Inhibitor

  摘要：

  We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC(50) approximate to 40 mu M in chamber cell migration assay).

  DOI：

  10.1021/ol800050g

文献信息

• Benzofuran-Derived Cyclic β-Amino Acid Scaffold for Building a Diverse Set of Flavonoid-Like Probes and the Discovery of a Cell Motility Inhibitor
  作者：Jyoti P. Nandy、Bojana Rakic、Bugga V. N. B. Sarma、Nallareddy Babu、Marc Lefrance、Gary D. Enright、Donald M. Leek、Kate Daniel、Luc A. Sabourin、Prabhat Arya

  DOI：10.1021/ol800050g

  日期：2008.3.1

  We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC(50) approximate to 40 mu M in chamber cell migration assay).