ethyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate | 1416051-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: ethyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate
• 英文别名: Ethyl 3-(4-piperidyloxy)benzothiophene-2-carboxylate；ethyl 3-piperidin-4-yloxy-1-benzothiophene-2-carboxylate
• CAS: 1416051-62-1
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: SJGNCSDGZZSPDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  硫代水杨酸甲酯 在 potassium tert-butylate 、 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 4.19h， 生成 ethyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-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

• [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。
• 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.