ethyl (2S,3S)-3-[(4-bromophenyl)methyl-prop-2-enoxycarbonylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate | 957918-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: ethyl (2S,3S)-3-[(4-bromophenyl)methyl-prop-2-enoxycarbonylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate
• CAS: 957918-77-3
• 化学式: C₂₆H₃₀BrNO₈
• 分子量: 564.43
• InChiKey: TZOCMUABDPKPFR-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3S)-3-[(4-bromophenyl)methyl-prop-2-enoxycarbonylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carboxylate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2S,3S)-2-(hydroxymethyl)-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate
  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-[(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

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).