4-({3-methyl-2-[(Z)-2-phenylethenyl]-1-benzofuran-4-yl}oxy)piperidine | 1402930-10-2

• 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: 4-({3-methyl-2-[(Z)-2-phenylethenyl]-1-benzofuran-4-yl}oxy)piperidine
• 英文别名: 4-[3-methyl-2-[(Z)-styryl]benzofuran-4-yl]oxypiperidine；4-[[3-methyl-2-[(Z)-2-phenylethenyl]-1-benzofuran-4-yl]oxy]piperidine
• CAS: 1402930-10-2
• 化学式: C₂₂H₂₃NO₂
• 分子量: 333.43
• InChiKey: SWHJTMXXIZUHER-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-({3-methyl-2-[(Z)-2-phenylethenyl]-1-benzofuran-4-yl}oxy)piperidine 在 1,4-环己二烯 、 palladium 10% on activated carbon 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以38%的产率得到4-{[3-methyl-2-(2-phenylethyl)-1-benzofuran-4-yl]oxy}piperidine
  参考文献：
  名称：

  Design and Synthesis of Inhibitors of Plasmodium falciparumN-Myristoyltransferase, A Promising Target for Antimalarial Drug Discovery

  摘要：

  Design of inhibitors for N-myristoyltransferase (NMT), an enzyme responsible for protein trafficking in Plasmodium falciparum, the most lethal species of parasites that cause malaria, is described. Chemistry-driven optimization of compound 1 from a focused NMT inhibitor library led to the identification of two early lead compounds 4 and 25, which showed good enzyme and cellular potency and excellent selectivity over human NMT. These molecules provide a valuable starting point for further development.

  DOI：

  10.1021/jm301160h
• 作为产物：
  描述：

  t-butyl 4-{[2-(ethoxycarbonyl)-3-methyl-1-benzofuran-4-yl]oxy}piperidine-1-carboxylate 在 magnesium oxide 、 lithium aluminium tetrahydride 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 4-({3-methyl-2-[(Z)-2-phenylethenyl]-1-benzofuran-4-yl}oxy)piperidine 、 4-({3-methyl-2-[(E)-2-phenylethenyl]-1-benzofuran-4-yl}oxy)piperidine
  参考文献：
  名称：

  Design and Synthesis of Inhibitors of Plasmodium falciparumN-Myristoyltransferase, A Promising Target for Antimalarial Drug Discovery

  摘要：

  Design of inhibitors for N-myristoyltransferase (NMT), an enzyme responsible for protein trafficking in Plasmodium falciparum, the most lethal species of parasites that cause malaria, is described. Chemistry-driven optimization of compound 1 from a focused NMT inhibitor library led to the identification of two early lead compounds 4 and 25, which showed good enzyme and cellular potency and excellent selectivity over human NMT. These molecules provide a valuable starting point for further development.

  DOI：

  10.1021/jm301160h

文献信息

• Design and Synthesis of Inhibitors of <i>Plasmodium falciparumN</i>-Myristoyltransferase, A Promising Target for Antimalarial Drug Discovery
  作者：Zhiyong Yu、James A. Brannigan、David K. Moss、A. Marek Brzozowski、Anthony J. Wilkinson、Anthony A. Holder、Edward W. Tate、Robin J. Leatherbarrow

  DOI：10.1021/jm301160h

  日期：2012.10.25

  Design of inhibitors for N-myristoyltransferase (NMT), an enzyme responsible for protein trafficking in Plasmodium falciparum, the most lethal species of parasites that cause malaria, is described. Chemistry-driven optimization of compound 1 from a focused NMT inhibitor library led to the identification of two early lead compounds 4 and 25, which showed good enzyme and cellular potency and excellent selectivity over human NMT. These molecules provide a valuable starting point for further development.