3-[[(1S,2S,4R)-2-bicyclo[2.2.1]heptanyl]oxy]-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-[[(1S,2S,4R)-2-bicyclo[2.2.1]heptanyl]oxy]-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide
• 化学式: C₂₀H₂₀Cl₂N₂O₃
• 分子量: 407.296
• InChiKey: AOGQPQXZFOWMDY-PEBVRCNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-3-(exo-bicyclo<2.2.1>hept-2-yloxy)-4-methoxybenzaldehyde 在 sodium chlorite 、 氯化亚砜 、 氨基磺酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.75h， 生成 3-[[(1S,2S,4R)-2-bicyclo[2.2.1]heptanyl]oxy]-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide
  参考文献：
  名称：

  Selective Type IV Phosphodiesterase Inhibitors as Antiasthmatic Agents. The Syntheses and Biological Activities of 3-(Cyclopentyloxy)-4-methoxybenzamides and Analogs

  摘要：

  The syntheses and biological activities of a number of benzamide derivatives, designed from rolipram, which are selective inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), are described. The effects of changes to the alkoxy groups, amide linkage, and benzamide N-phenyl ring on the inhibition of the cytosolic PDE IV from pig aorta have been investigated. As a result, some highly potent and selective PDE IV inhibitors have been identified. The most potent compounds have been further evaluated for their inhibitory potencies against PDE IV obtained from and superoxide O-2(-) generation from guinea pig eosinophils in vitro. Selected compounds have also been examined for their activities in inhibiting histamine-induced bronchospasm in anaesthetized guinea pigs. 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide (15j) showed exceptional potency in all tests and may have therapeutic potential in the treatment of asthma.

  DOI：

  10.1021/jm00037a021

文献信息

• Selective Type IV Phosphodiesterase Inhibitors as Antiasthmatic Agents. The Syntheses and Biological Activities of 3-(Cyclopentyloxy)-4-methoxybenzamides and Analogs
  作者：Michael J. Ashton、David C. Cook、Garry Fenton、Jan-Anders Karlsson、Malcolm N. Palfreyman、David Raeburn、Andrew J. Ratcliffe、John E. Souness、Suga Thurairatnam、Nigel Vicker

  DOI：10.1021/jm00037a021

  日期：1994.5

  The syntheses and biological activities of a number of benzamide derivatives, designed from rolipram, which are selective inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), are described. The effects of changes to the alkoxy groups, amide linkage, and benzamide N-phenyl ring on the inhibition of the cytosolic PDE IV from pig aorta have been investigated. As a result, some highly potent and selective PDE IV inhibitors have been identified. The most potent compounds have been further evaluated for their inhibitory potencies against PDE IV obtained from and superoxide O-2(-) generation from guinea pig eosinophils in vitro. Selected compounds have also been examined for their activities in inhibiting histamine-induced bronchospasm in anaesthetized guinea pigs. 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide (15j) showed exceptional potency in all tests and may have therapeutic potential in the treatment of asthma.