(+/-)-3-(exo-bicyclo<2.2.1>hept-2-yloxy)-4-methoxybenzaldehyde

• 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-(exo-bicyclo<2.2.1>hept-2-yloxy)-4-methoxybenzaldehyde
• 英文别名: 3-[[(1S,2S,4R)-2-bicyclo[2.2.1]heptanyl]oxy]-4-methoxybenzaldehyde
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: QQWFEXZXSDELSH-OSMZGAPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(exo-bicyclo<2.2.1>hept-2-yloxy)-4-methoxybenzaldehyde 在 吡啶 、 sodium chlorite 、 氯化亚砜 、 氨基磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 3-[[(1S,2S,4R)-2-bicyclo[2.2.1]heptanyl]oxy]-N-(2,6-dichlorophenyl)-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
• 作为产物：
  描述：

  异香兰素 、 (+/-)-endo-2-norborneol 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 48.0h， 以75%的产率得到(+/-)-3-(exo-bicyclo<2.2.1>hept-2-yloxy)-4-methoxybenzaldehyde
  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

• Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders
  申请人：PFIZER INC.

  公开号：EP0428313A2

  公开（公告）日：1991-05-22

  Racemic or optionally active compound of the formula wherein X is O or NH, R¹ is a (C₇-C₁₁)polycycloalkyl group, R² is methyl or ethyl, Y is R³ is hydrogen, (C₁-C₃)alkyl, (C₂-C₃)alkenyl, benzyl or phenethyl, and R⁴ is hydrogen, (C₁-C₃)alkyl or (C₂-C₃)alkanoyl, are useful in the treatment of asthma or inflammatory airway or skin diseases.

  式中的外消旋或任选活性化合物 其中 X 是 O 或 NH，R¹ 是 (C₇-C₁₁)多环烷基，R² 是甲基或乙基，Y 是 R³ 是氢、(C₁-C₃)烷基、(C₂-C₃)烯基、苄基或苯乙基，R⁴ 是氢、(C₁-C₃)烷基或 (C₂-C₃)烷酰基。
• Enzymatic resolution of endo-bicycle(2.2.1)-heptan-2-ol and derived pharmaceutical agents
  申请人：PFIZER INC.

  公开号：EP0428302A2

  公开（公告）日：1991-05-22

  Process for the pancreatic lipase mediated trans­esterification method for the optical resolution of endo-norborneol; derived optically active 5-(3-(exo-­bicyclo[2.2.1]hept-2-yloxy)-4-methoxyphenyl)-3,4,5,6-­tetrahydropyrimidin-2(1H)-ones; and stepwise process and intermediates therefor.

  胰脂肪酶介导的酯交换法光学分解内山梨醇的工艺；衍生的具有光学活性的 5-(3-(外-双环[2.2.1]庚-2-氧基)-4-甲氧基苯基)-3,4,5,6-四氢嘧啶-2(1H)-酮；及其分步工艺和中间体。
• Calcium-independent phosphodiesterase inhibitors as putative antidepressants: [3-(bicycloalkyloxy)-4-methoxyphenyl-2-imidazolidinones
  作者：Nicholas A. Saccomano、Frederic J. Vinick、B. Kenneth Koe、Jann A. Nielsen、William M. Whalen、Morgan Meltz、Douglas Phillips、Peter F. Thadieo、Stanley Jung、Douglas C. Chapin、Lorraine A. Lebel、Lorena L. Russo、David L. Helweg、Jonathan L. Johnson Jr、Jeffery L. Ives、Ian H. Williams

  DOI：10.1021/jm00105a045

  日期：1991.1

  The synthesis and biological properties of a novel series of selective calcium-independent phosphodiesterase inhibitors are described. These compounds also inhibit the specific binding of [H-3]rolipram to rat brain membranes and exhibit efficacy in preclinical models of antidepressant activity in mice, such as reducing immobility in the forced-swim test and reversing reserpine-induced hypothermia. Imidazolidinones 4 and 16 were found to be the most potent compounds studied.
• US5270206A
  申请人：——

  公开号：US5270206A

  公开（公告）日：1993-12-14
• US5342842A
  申请人：——

  公开号：US5342842A

  公开（公告）日：1994-08-30