(2E)-1-[3-methyl-4-(piperidin-4-yloxy)-1-benzofuran-2-yl]-3-phenylprop-2-en-1-one | 1402930-18-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-1-[3-methyl-4-(piperidin-4-yloxy)-1-benzofuran-2-yl]-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-[3-methyl-4-(4-piperidyloxy)benzofuran-2-yl]-3-phenyl-prop-2-en-1-one；(E)-1-(3-methyl-4-piperidin-4-yloxy-1-benzofuran-2-yl)-3-phenylprop-2-en-1-one
• CAS: 1402930-18-0
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: KBIFWZQIMFMMRS-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-1-[3-methyl-4-(piperidin-4-yloxy)-1-benzofuran-2-yl]-3-phenylprop-2-en-1-one 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41%的产率得到1-[3-Methyl-4-(Piperidin-4-Yloxy)-1-Benzofuran-2-Yl]-3-Phenylpropan-1-One
  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：

  tert-butyl 4-[(2-acetyl-3-methyl-1-benzofuran-4-yl)oxy]piperidine-1-carboxylate 在 三氟乙酸 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2E)-1-[3-methyl-4-(piperidin-4-yloxy)-1-benzofuran-2-yl]-3-phenylprop-2-en-1-one
  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.