[3-[methylcarbamoyl-[(4-tetradecoxyphenyl)methyl]amino]phenyl]methyl N-methylcarbamate | 138830-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3-[methylcarbamoyl-[(4-tetradecoxyphenyl)methyl]amino]phenyl]methyl N-methylcarbamate
• CAS: 138830-59-8
• 化学式: C₃₂H₄₉N₃O₄
• 分子量: 539.759
• InChiKey: ORRDTAXGDYUDFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  39
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3-[methylcarbamoyl-[(4-tetradecoxyphenyl)methyl]amino]phenyl]methyl N-methylcarbamate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以6.9 g的产率得到N-<3-(hydroxymethyl)phenyl>-N'-methyl-N-<<4-(tetradecyloxy)phenyl>methyl>urea
  参考文献：
  名称：

  Analogs of platelet activating factor. 7. Bis-aryl amide and bis-aryl urea receptor antagonists of PAF

  摘要：

  A series of bis-aryl amide (13-57 and 66-81) and bis-aryl urea (58 and 85) antagonists of platelet-activating factor (PAF) was prepared that contain, separating the two aromatic rings, linear amide linkages of the form -(CH2)nCONH- (n = 0-2), -OCH2CONH-, and -(CH2)nNHCO- (n = 0-1), branched amide linkages of the form -(CH2)nN(COR)- (n = 1-3, R = CH3 or n-C3H7), and -N(COCH3)CH2-, and urea linkages of the form -NHCONH- and -CH2N(CONHCH3)-. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. These in vitro data were compared to similar data obtained for a number of known PAF antagonists. The compounds were evaluated in vivo, in the mouse, for their ability to prevent death induced by a lethal challenge of PAF. The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied. Best activity was observed for compounds having linkages of the type -CH2CONH-, -CH2N(COR)-, and -CH2NHCO-. Many of these compounds inhibit PAF-induced platelet aggregation with IC50's under 1 muM.

  DOI：

  10.1021/jm00104a002
• 作为产物：
  描述：

  3-氨基苯甲醇 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.0h， 生成 [3-[methylcarbamoyl-[(4-tetradecoxyphenyl)methyl]amino]phenyl]methyl N-methylcarbamate
  参考文献：
  名称：

  Analogs of platelet activating factor. 7. Bis-aryl amide and bis-aryl urea receptor antagonists of PAF

  摘要：

  A series of bis-aryl amide (13-57 and 66-81) and bis-aryl urea (58 and 85) antagonists of platelet-activating factor (PAF) was prepared that contain, separating the two aromatic rings, linear amide linkages of the form -(CH2)nCONH- (n = 0-2), -OCH2CONH-, and -(CH2)nNHCO- (n = 0-1), branched amide linkages of the form -(CH2)nN(COR)- (n = 1-3, R = CH3 or n-C3H7), and -N(COCH3)CH2-, and urea linkages of the form -NHCONH- and -CH2N(CONHCH3)-. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. These in vitro data were compared to similar data obtained for a number of known PAF antagonists. The compounds were evaluated in vivo, in the mouse, for their ability to prevent death induced by a lethal challenge of PAF. The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied. Best activity was observed for compounds having linkages of the type -CH2CONH-, -CH2N(COR)-, and -CH2NHCO-. Many of these compounds inhibit PAF-induced platelet aggregation with IC50's under 1 muM.

  DOI：

  10.1021/jm00104a002

文献信息

• Bis-aryl amide and urea antagonists of platelet activating factor
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0458037A1

  公开（公告）日：1991-11-27

  Bis-aryl amide and urea compounds of the general formula: wherein X is a divalent amide or urea substituent and Y is a nitrogen containing heterocycle, which compounds are inhibitors of platelet activating factor. Pharmaceutical compositions containing the compounds and methods of treating platelet activating factor associated conditions are also included.

  通式如下的双芳基酰胺和脲化合物： 其中 X 是二价酰胺或脲取代基，Y 是含氮杂环，这些化合物是血小板活化因子的抑制剂。还包括含有这些化合物的药物组合物和治疗血小板活化因子相关疾病的方法。
• US5077409A
  申请人：——

  公开号：US5077409A

  公开（公告）日：1991-12-31
• US5128351A
  申请人：——

  公开号：US5128351A

  公开（公告）日：1992-07-07
• US5225425A
  申请人：——

  公开号：US5225425A

  公开（公告）日：1993-07-06
• US5231182A
  申请人：——

  公开号：US5231182A

  公开（公告）日：1993-07-27