4-{2-[1-(6-Methyl-pyridazin-3-yl)-piperidin-4-yl]-ethoxy}-benzaldehyde O-ethyl-oxime | 314062-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-{2-[1-(6-Methyl-pyridazin-3-yl)-piperidin-4-yl]-ethoxy}-benzaldehyde O-ethyl-oxime
• 英文别名: Benzaldehyde, 4-(2-(1-(6-methyl-3-pyridazinyl)-4-piperidinyl)ethoxy)-, O-ethyloxime；(E)-N-ethoxy-1-[4-[2-[1-(6-methylpyridazin-3-yl)piperidin-4-yl]ethoxy]phenyl]methanimine
• CAS: 314062-80-1
• 化学式: C₂₁H₂₈N₄O₂
• 分子量: 368.479
• InChiKey: LNKHWGSSSPTTHB-CJLVFECKSA-N

物化性质

• 沸点：
  567.0±60.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-hydroxybenzaldehyde O-ethyloxime 、 2-(1-(6-甲基吡嗪-3-基)哌啶-4-基)乙醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到4-{2-[1-(6-Methyl-pyridazin-3-yl)-piperidin-4-yl]-ethoxy}-benzaldehyde O-ethyl-oxime
  参考文献：
  名称：

  An Orally Bioavailable Oxime Ether Capsid Binder with Potent Activity against Human Rhinovirus

  摘要：

  A series of capsid-binding compounds was screened against human rhinovirus (HRV) using a CPE based assay. The ethyl oxime ether 14 was found to have outstanding anti-HRV activity (median IC50 4.75 ng/mL), and unlike the equivalent ethyl ester compound 3 (Pirodavir), it has good oral bioavailability, making it a promising development candidate. Compound 14 illustrates that an oxime ether group can act as a metabolically stable bioisostere for an ester functionality.

  DOI：

  10.1021/jm0202876

文献信息

• US7078403B1
  申请人：——

  公开号：US7078403B1

  公开（公告）日：2006-07-18
• An Orally Bioavailable Oxime Ether Capsid Binder with Potent Activity against Human Rhinovirus
  作者：Keith G. Watson、Renee N. Brown、Rachel Cameron、David K. Chalmers、Stephanie Hamilton、Betty Jin、Guy Y. Krippner、Angela Luttick、Darryl B. McConnell、Phillip A. Reece、Jane Ryan、Pauline C. Stanislawski、Simon P. Tucker、Wen-Yang Wu、Dale L. Barnard、Robert W. Sidwell

  DOI：10.1021/jm0202876

  日期：2003.7.1

  A series of capsid-binding compounds was screened against human rhinovirus (HRV) using a CPE based assay. The ethyl oxime ether 14 was found to have outstanding anti-HRV activity (median IC50 4.75 ng/mL), and unlike the equivalent ethyl ester compound 3 (Pirodavir), it has good oral bioavailability, making it a promising development candidate. Compound 14 illustrates that an oxime ether group can act as a metabolically stable bioisostere for an ester functionality.