ethyl 3-methyl-4-{[1-(triphenylmethyl)-piperidin-4-yl]oxy}-1-benzofuran-2-carboxylate | 1402930-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ethyl 3-methyl-4-{[1-(triphenylmethyl)-piperidin-4-yl]oxy}-1-benzofuran-2-carboxylate
• 英文别名: Ethyl 3-methyl-4-(1-tritylpiperidin-4-yl)oxy-1-benzofuran-2-carboxylate；ethyl 3-methyl-4-(1-tritylpiperidin-4-yl)oxy-1-benzofuran-2-carboxylate
• CAS: 1402930-43-1
• 化学式: C₃₆H₃₅NO₄
• 分子量: 545.678
• InChiKey: TXZDNIOBVUFELC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-methyl-4-{[1-(triphenylmethyl)-piperidin-4-yl]oxy}-1-benzofuran-2-carboxylate 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-{[3-methyl-2-(phenoxymethyl)-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：

  乙基4-羟基-3-甲基-1-苯并呋喃-2-羧酸酯 、 N-triphenylmethyl-4-hydroxypiperidine 在 三苯基膦 、 N-Boc-4-羟基哌啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以65%的产率得到ethyl 3-methyl-4-{[1-(triphenylmethyl)-piperidin-4-yl]oxy}-1-benzofuran-2-carboxylate
  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

• [EN] NOVEL COMPOUNDS AND THEIR USE IN THERAPY<br/>[FR] NOUVEAUX COMPOSÉS ET LEUR UTILISATION EN THÉRAPIE
  申请人：IMP INNOVATIONS LTD

  公开号：WO2013083991A1

  公开（公告）日：2013-06-13

  The invention provides compounds which inhibit N-myristoyltransferase and are selective for protozoal N-myristoyltransferase and, consequently suitable to treat microbial infections, including viral and fungal infections, and protozoan infections such as malaria, leishmaniasis and sleeping sickness.

  这项发明提供了抑制N-肉豆蔻酰基转移酶并且对原生动物N-肉豆蔻酰基转移酶具有选择性的化合物，因此适用于治疗微生物感染，包括病毒和真菌感染，以及疟疾、利什曼病和睡眠病等原生动物感染。
• 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.