3-[[4-(dodecyloxy)-1-naphthalenyl]oxy]-2-methoxy-1-propanol | 127164-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[[4-(dodecyloxy)-1-naphthalenyl]oxy]-2-methoxy-1-propanol
• 英文别名: 3-(4-Dodecoxynaphthalen-1-yl)oxy-2-methoxypropan-1-ol
• CAS: 127164-61-8
• 化学式: C₂₆H₄₀O₄
• 分子量: 416.601
• InChiKey: ZOTZKBAZLBFLFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[[4-(dodecyloxy)-1-naphthalenyl]oxy]-2-methoxy-1-propanol 在 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 甲苯 为溶剂， 反应 43.0h， 生成 3-(3-{[3-(4-Dodecyloxy-naphthalen-1-yloxy)-2-methoxy-propoxy]-hydroxy-phosphoryloxy}-benzyl)-thiazol-3-ium
  参考文献：
  名称：

  Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor

  摘要：

  A series of aryl phosphoglyceride (3, 19-6 1) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared. A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. Selected compounds were also evaluated for their ability to displace [H-3]PAF from its receptor on 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 both the mouse and rabbit, 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. Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.

  DOI：

  10.1021/jm00087a023
• 作为产物：
  描述：

  4-(dodecyloxy)-1-naphthalenol 在 吡啶 、 amberlyst-15 、 硫酸 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 3-[[4-(dodecyloxy)-1-naphthalenyl]oxy]-2-methoxy-1-propanol
  参考文献：
  名称：

  Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor

  摘要：

  A series of aryl phosphoglyceride (3, 19-6 1) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared. A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. Selected compounds were also evaluated for their ability to displace [H-3]PAF from its receptor on 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 both the mouse and rabbit, 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. Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.

  DOI：

  10.1021/jm00087a023

文献信息

• Novel antagonists of platelet activating factor
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0336142A2

  公开（公告）日：1989-10-11

  The invention is a compound of R or S enantiomers or racemic mixtures of compounds of the formula: wherein: (A) X is (i) C1-C24 (ii) C1-C24 alkoxy; (iii) C1-C24 carboamoyloxy; or wherein n is an integer from 1 to 25 and m is an integer from 0 to 24 and the sum of n and m is less than or equal to 25; (v) phenyl; (vi) mono- or polysubstituted phenyl substituted with C1-C20 alkyl, C1-C20 alkoxy, halogen, trifluoromethyl, phenyl, substituted phenyl or benzyloxy; (vii) phenoxy; (viii) mono- or polysubstituted phenoxy substituted with C1-C20 alkyl, Ci-C2o alkoxy, halogen, trifluoromethyl, phenyl substituted phenyl or benzyloxy; (ix) naphthaloxy; (x) mono- or polysubstituted naphthaloxy substituted with C1-C20 alkyl, C1-C20 alkoxy or halogen; (xi) -O-(CH2)r-O-((CH2)pO)t-(CH2)a-W wherein W is methyl or phenyl optionally substituted with C,-C3 alkyl, C1-C3 alkoxy or phenyl, r, p, t and a are integers such that the expression r + (p + 1)t + a is also an integer and has a value of 3 to 20; r is greater than or equal to 2; p is greater than or equal to 2; t is greater than or equal to zero; and a is greater than or equal to zero; (B) i is an integer from 1 to 3 and j is an integer from 1 to 6; (C) Q is -OR2, or O-C-R2, wherein R2 is hydrogen, C1-C6 alkyl or C1-C6 alkenyl; (D) Y is a divalent radical or (E) the moiety R3 represents one or more C1-C5 alkyl, C1-C5 alkoxy or halogen substituents of the aromatic ring; (F) the moiety -CH2A may be in the ortho, meta or para position wherein A is (i) a 5-7 member aromatic heterocyclic ring containing at least one nitrogen and one or more nitrogen or sulfur atoms: (ii) or (iii) which are PAF inhibitors.

  本发明是一种 R 或 S 对映体的化合物或式中化合物的外消旋混合物： 其中 (A) X 是 (i) C1-C24 (ii) C1-C24 烷氧基 (iii) C1-C24 碳酰胺氧基； 或 其中 n 为 1 至 25 的整数，m 为 0 至 24 的整数，且 n 与 m 之和小于或等于 25； (v) 苯基 (vi) 被 C1-C20 烷基、C1-C20 烷氧基、卤素、三氟甲基、苯基、取代苯基 或苄氧基取代的单取代或多取代苯基； (vii) 苯氧基 (viii) 被 C1-C20 烷基、C1-C2o 烷氧基、卤素、三氟甲基、苯基、取代苯基 或苄氧基取代的单取代或多取代苯氧基； (ix) 萘氧基 (x) 被 C1-C20 烷基、C1-C20 烷氧基或卤素取代的单取代或多取代萘氧基； (xi) -O-(CH2)r-O-((CH2)pO)t-(CH2)a-W，其中 W 是甲基或任选被 C,-C3烷基、C1-C3 烷氧基或苯基取代的苯基，r、p、t 和 a 是整数，使得表达式 r + (p + 1)t + a 也是整数，且值为 3 至 20；r 大于或等于 2；p 大于或等于 2；t 大于或等于零；a 大于或等于零； (B) i 是 1 至 3 的整數，j 是 1 至 6 的整數； (C) Q 为-OR2、 或 O-C-R2，其中 R2 是氢、C1-C6 烷基或 C1-C6 烯基； (D) Y 是二价基 或 (E) 分子 R3 代表芳环的一个或多个 C1-C5 烷基、C1-C5 烷氧基或卤素取代基； (F) 分子 -CH2A 可位于正位、偏位或对位，其中 A 是 (i) 包含至少一个氮原子和一个或多个氮或硫原子的 5-7 个芳香杂环： (ii) 或 (iii) 或 是 PAF 抑制剂。
• US5234918A
  申请人：——

  公开号：US5234918A

  公开（公告）日：1993-08-10
• US5215975A
  申请人：——

  公开号：US5215975A

  公开（公告）日：1993-06-01
• US5411983A
  申请人：——

  公开号：US5411983A

  公开（公告）日：1995-05-02
• Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor
  作者：A. Wissner、M. L. Carroll、K. E. Green、S. S. Kerwar、W. C. Pickett、R. E. Schaub、L. W. Torley、S. Wrenn、C. A. Kohler

  DOI：10.1021/jm00087a023

  日期：1992.5

  A series of aryl phosphoglyceride (3, 19-6 1) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared. A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. Selected compounds were also evaluated for their ability to displace [H-3]PAF from its receptor on 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 both the mouse and rabbit, 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. Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.