4-(十四烷氧基)苯乙酸甲酯 | 62442-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(十四烷氧基)苯乙酸甲酯
• 英文名称: 4-(tetradecyloxy)benzeneacetic acid methyl ester
• 英文别名: methyl [4-(tetradecyloxy)phenyl]acetate；[4-(Tetradecyloxy)phenyl]acetic acid methyl ester；methyl 2-(4-tetradecoxyphenyl)acetate
• CAS: 62442-93-7
• 化学式: C₂₃H₃₈O₃
• 分子量: 362.553
• InChiKey: USPJDDPQZBXVRU-UHFFFAOYSA-N

物化性质

• 熔点：
  37 °C
• 沸点：
  453.2±20.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)

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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(十四烷氧基)苯乙酸甲酯 在 吡啶 、 氢氧化钾 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 N-[(2-Hydroxymethyl)phenyl]-4-(tetradecyloxy) benzeneacetamide
  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：

  溴代十四烷 、 4-羟基苯乙酸甲酯 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(十四烷氧基)苯乙酸甲酯
  参考文献：
  名称：

  5-（四贸易基氧基）-2-呋喃羧酸和相关的降血脂脂肪酸样烷氧基芳基羧酸。

  摘要：

  发现5-（四氢癸氧基）-2-呋喃羧酸（91，RMI 14514）可以降低血脂并抑制脂肪酸合成，对肝脏重量和肝脏脂肪含量的影响最小。这种类似脂肪酸的化合物代表了一类新的降血脂药。对大鼠和猴子有效。该化合物的产生是由于发现了某些β-酮酸酯的降血脂活性，假定和确认了相应的苯甲酸作为活性代谢物以及系统地研究了结构-活性关系。

  DOI：

  10.1021/jm00216a009

文献信息

• Inhibition of secretory phospholipase A. 1-Design, synthesis and structure–activity relationship studies starting from 4-tetradecyloxybenzamidine to obtain specific inhibitors of group II sPLAs
  作者：L ASSOGBA、A AHAMADAHIMIDI、N HABICH、D AOUN、L BOUKLI、F MASSICOT、C MOUNIER、J HUET、A LAMOURI、J OMBETTA

  DOI：10.1016/j.ejmech.2005.03.027

  日期：2005.9

  this work the discovery of the specificity through design, synthesis and structure-activity relationships studies of different kinds of PMS815 derivatives. The leading compound, 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one (9b, PMS1062) exhibits a micromolar IC50 towards three group II PLA2s, while inactive towards four group I and one group III enzymes in two in vitro enzymatic assay

  从GI和GII PLA2s的非特异性抑制剂4-十四烷氧基苯甲m（PMS815）开始，我们在这项工作中报告了通过设计，合成和不同种类的PMS815衍生物的结构活性关系研究发现特异性。领先的化合物4,5-二氢-3-（4-十四烷基氧基苄基）-1,2,4-4H-恶二唑-5-酮（9b，PMS1062）对3个II类PLA2表现出微摩尔IC50，对4个PLA2则无活性在两种体外酶分析条件下，第I组和第III组酶。它还能够阻断HepG2细胞系中LPS和IL-6诱导的PLA2-II活性，并且在两种不同的细胞系（A549和LLC-PK1）中测试PMS1062的浓度高达100 microM时，未观察到细胞毒性。 。
• Pyridinium compounds which are useful as antagonists of platelet
  申请人：American Cyanamid Company

  公开号：US05208247A1

  公开（公告）日：1993-05-04

  The invention is aryl, amide, imide and carbamate pyridine antagonists of platelet activating factor.

  这项发明是有机芳基、酰胺、亚胺和碳酸酯吡啶拮抗剂，用于抑制血小板活化因子。
• Aryl pyridinium compounds which are useful in treating shock
  申请人：American Cyanamid Company

  公开号：US05328921A1

  公开（公告）日：1994-07-12

  The invention is aryl, amide, imide and carbamate pyridine antagonists of platelet activating factor.

  这项发明是关于芳基、酰胺、亚酰胺和氨基甲酸酯吡啶类抗血小板活化因子拮抗剂。
• 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。
• Aryl, amide, imide, and carbamate pyridine antagonists of platelet activating factor
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0530444A1

  公开（公告）日：1993-03-10

  Pyridine derivatives of the general formula wherein:    X is a divalent radical of: are PAF antagonists. Processes for their preparation and pharmaceutical compositions containing them are also included.

  通式如下的吡啶衍生物 其中 X 是下列物质的二价基 是 PAF 拮抗剂。它们的制备方法和含有它们的药物组合物也包括在内。