3-(p-tetradecyloxyphenyl)propionic acid | 65686-14-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(p-tetradecyloxyphenyl)propionic acid
• 英文别名: Benzenepropanoic acid, 4-(tetradecyloxy)-；3-(4-tetradecoxyphenyl)propanoic acid
• CAS: 65686-14-8
• 化学式: C₂₃H₃₈O₃
• 分子量: 362.553
• InChiKey: ICQMIQQAHAIYAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(p-tetradecyloxyphenyl)propionic acid 在 吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[3-(bromomethyl)phenyl]-3-(4-tetradecoxyphenyl)propanamide
  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：

  对羟基苯丙酸甲酯 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 3-(p-tetradecyloxyphenyl)propionic acid
  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

• Chirale Verbindungen
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0714904A1

  公开（公告）日：1996-06-05

  Chirale Verbindungen der allgemeinen Formel I in der R¹Wasserstoff oder ein Rest der Formel -Y-Z-Y¹, R²ein Rest der Formel und XWasserstoff, Fluor, Chlor, Brom, Jod, Hydroxy oder OR¹ sind, wobei Yeine direkte Bindung, CO oder C₂- bis C₈-Alkylen, in welchem nichtbenachbarte C-Atome durch O, CO, COO oder OCO ersetzt sein können Zeine Gruppe, die einen oder mehrere gesättigte oder ungesättigte, gegebenenfalls Heteroatome aufweisende Ringe enthält, Y¹C₁- bis C₁₅-Alkyl, C₂- bis C₁₅-Alkenyl, C₁- bis C₁₅-Alkoxy, C₂- bis C₁₅-Alkenyloxy, C₁- bis C₁₅-Alkanoyloxy oder C₃- bis C₁₅-Alkenoyloxy, wobei in diesen Resten nichtbenachbarte Kohlenstoffatome durch Sauerstoff, OCO oder COO ersetzt sein können, und n0,1 oder 2 bedeuten.

  通式 I 的手性化合物 中的 R¹ 是氢或式 -Y-Z-Y¹ 的基、 R² 是式中的一个基团 和 X是氢、氟、氯、溴、碘、羟基或OR¹，其中 Y 是直接键、CO 或 C₂-至 C₈-亚烷基，其中不相邻的 C 原子可由 O、CO、COO 或 OCO 取代 含有一个或多个饱和或不饱和环的基团，可选择含有杂原子、 Y¹C₁- to C₁₅-alkyl, C₂- to C₁₅-alkenyl, C₁- to C₁₅-alkoxy, C₂- to C₁₅-alkenyloxy, C₁- to C₁₅-alkanoyloxy 或 C₃- to C₁₅-alkenoyloxy、其中这些自由基中的非相邻碳原子可被氧、OCO 或 COO 取代，以及 表示 0、1 或 2。
• JPS52131552A
  申请人：——

  公开号：JPS52131552A

  公开（公告）日：1977-11-04
• US5709817A
  申请人：——

  公开号：US5709817A

  公开（公告）日：1998-01-20
• US5820783A
  申请人：——

  公开号：US5820783A

  公开（公告）日：1998-10-13
• Analogs of platelet activating factor. 7. Bis-aryl amide and bis-aryl urea receptor antagonists of PAF
  作者：Allan Wissner、Marion L. Carroll、Bernard D. Johnson、Suresh S. Kerwar、Walter C. Pickett、Robert E. Schaub、Lawrence W. Torley、Michael P. Trova、Constance A. Kohler

  DOI：10.1021/jm00104a002

  日期：1992.12

  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.