tert-butyl 4-((2-(benzylcarbamoyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate | 1416051-70-1

• 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: tert-butyl 4-((2-(benzylcarbamoyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate
• 英文别名: Tert-butyl 4-[[2-(benzylcarbamoyl)-1-benzothiophen-3-yl]oxy]piperidine-1-carboxylate；tert-butyl 4-[[2-(benzylcarbamoyl)-1-benzothiophen-3-yl]oxy]piperidine-1-carboxylate
• CAS: 1416051-70-1
• 化学式: C₂₆H₃₀N₂O₄S
• 分子量: 466.601
• InChiKey: XMSRWHIWOOKDSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  96.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-((2-(benzylcarbamoyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以40%的产率得到N-benzyl-3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxamide
  参考文献：
  名称：

  Discovery of Novel and Ligand-Efficient Inhibitors of Plasmodium falciparum and Plasmodium vivaxN-Myristoyltransferase

  摘要：

  N-Myristoyltransferase (NMT) is an attractive antiprotozoan drug target. A lead-hopping approach was utilized in the design and synthesis of novel benzo[b]thiophene-containing inhibitors of Plasmodium falciparum (Pf) and Plasmodium vivax (Pv) NMT. These inhibitors are selective against Homo sapiens NMT1 (HsNMT), have excellent ligand efficiency (LE), and display antiparasitic activity in vitro. The binding mode of this series was determined by crystallography and shows a novel binding mode for the benzothiophene ring.

  DOI：

  10.1021/jm301474t
• 作为产物：
  描述：

  硫代水杨酸甲酯 在 lithium hydroxide monohydrate 、 potassium tert-butylate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 25.69h， 生成 tert-butyl 4-((2-(benzylcarbamoyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate
  参考文献：
  名称：

  Discovery of Novel and Ligand-Efficient Inhibitors of Plasmodium falciparum and Plasmodium vivaxN-Myristoyltransferase

  摘要：

  N-Myristoyltransferase (NMT) is an attractive antiprotozoan drug target. A lead-hopping approach was utilized in the design and synthesis of novel benzo[b]thiophene-containing inhibitors of Plasmodium falciparum (Pf) and Plasmodium vivax (Pv) NMT. These inhibitors are selective against Homo sapiens NMT1 (HsNMT), have excellent ligand efficiency (LE), and display antiparasitic activity in vitro. The binding mode of this series was determined by crystallography and shows a novel binding mode for the benzothiophene ring.

  DOI：

  10.1021/jm301474t

文献信息

• Discovery of Novel and Ligand-Efficient Inhibitors of Plasmodium falciparum and Plasmodium vivax<i>N</i>-Myristoyltransferase
  作者：Mark D. Rackham、James A. Brannigan、David K. Moss、Zhiyong Yu、Anthony J. Wilkinson、Anthony A. Holder、Edward W. Tate、Robin J. Leatherbarrow

  DOI：10.1021/jm301474t

  日期：2013.1.10

  N-Myristoyltransferase (NMT) is an attractive antiprotozoan drug target. A lead-hopping approach was utilized in the design and synthesis of novel benzo[b]thiophene-containing inhibitors of Plasmodium falciparum (Pf) and Plasmodium vivax (Pv) NMT. These inhibitors are selective against Homo sapiens NMT1 (HsNMT), have excellent ligand efficiency (LE), and display antiparasitic activity in vitro. The binding mode of this series was determined by crystallography and shows a novel binding mode for the benzothiophene ring.