(4R,4aS,9bS)-4-benzylsulfanyl-1-[(4-bromophenyl)methyl]-7-(2-methoxyethoxymethoxy)-3,4,4a,9b-tetrahydro-[1]benzofuro[3,2-b]pyridin-2-one | 1016896-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (4R,4aS,9bS)-4-benzylsulfanyl-1-[(4-bromophenyl)methyl]-7-(2-methoxyethoxymethoxy)-3,4,4a,9b-tetrahydro-[1]benzofuro[3,2-b]pyridin-2-one
• CAS: 1016896-57-3
• 化学式: C₂₉H₃₀BrNO₅S
• 分子量: 584.531
• InChiKey: NTYGZTSBXCHIQX-XNFLFYSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4aR,9bS)-1-[(4-bromophenyl)methyl]-7-(2-methoxyethoxymethoxy)-4a,9b-dihydro-[1]benzofuro[3,2-b]pyridin-2-one 、 苄硫醇 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以69%的产率得到(4R,4aS,9bS)-4-benzylsulfanyl-1-[(4-bromophenyl)methyl]-7-(2-methoxyethoxymethoxy)-3,4,4a,9b-tetrahydro-[1]benzofuro[3,2-b]pyridin-2-one
  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).