Phosphoric acid 4,4-bis-(8-chloro-2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-6-yl)-but-3-enyl ester 1-methyl-2-oxo-propyl ester (Z)-octadec-9-enyl ester | 173173-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: Phosphoric acid 4,4-bis-(8-chloro-2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-6-yl)-but-3-enyl ester 1-methyl-2-oxo-propyl ester (Z)-octadec-9-enyl ester
• 英文别名: 4,4-bis(8-chloro-2,2-dimethyl-4-oxo-1,3-benzodioxin-6-yl)but-3-enyl [(Z)-octadec-9-enyl] 3-oxobutan-2-yl phosphate
• CAS: 173173-64-3
• 化学式: C₄₆H₆₃Cl₂O₁₁P
• 分子量: 893.879
• InChiKey: HOISEJJHSSDFPP-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  60
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Phosphoric acid 4,4-bis-(8-chloro-2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-6-yl)-but-3-enyl ester 1-methyl-2-oxo-propyl ester (Z)-octadec-9-enyl ester 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以65%的产率得到4,4-(3',3"-dicarboxy-5',5"-dichloro-4',4"-dihydroxydiphenyl)-3-buten-1-yl oleyl phosphate
  参考文献：
  名称：

  Correlation of Anti-HIV Potency with Lipophilicity in a Series of Cosalane Analogs Having Normal Alkenyl and Phosphodiester Chains as Cholestane Replacements

  摘要：

  In order to define the role of the cholestane moiety in the anti-HIV agent cosalane, a series of cosalane analogs was synthesized in which the cholestane ring system was replaced by normal alkenyl and phosphodiester substituents having varied chain lengths and lipophilicities. The compounds containing simple alkenyl substituents were found to be more potent as inhibitors of the cytopathic effect of HIV-1 in cell culture than the phosphodiesters. In addition, the potencies of the alkene congeners correlated positively with chain length and lipophilicity of the alkene. The results indicate that the cholestane moiety of cosalane functions as a lipophilic accessory appendage to escort the dichlorodisalicylmethane pharmacophore to a lipid environment.

  DOI：

  10.1021/jm950666h
• 作为产物：
  描述：

  1,1-bis[8',8"-dichloro-2',2',2",2"-tetramethyl-4',4"-dioxo-6',6"-(1,3-benzodioxyl)]-4-[(tert-butyldimethylsilyl)oxy]-1-butene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 27.75h， 生成 Phosphoric acid 4,4-bis-(8-chloro-2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-6-yl)-but-3-enyl ester 1-methyl-2-oxo-propyl ester (Z)-octadec-9-enyl ester
  参考文献：
  名称：

  Correlation of Anti-HIV Potency with Lipophilicity in a Series of Cosalane Analogs Having Normal Alkenyl and Phosphodiester Chains as Cholestane Replacements

  摘要：

  In order to define the role of the cholestane moiety in the anti-HIV agent cosalane, a series of cosalane analogs was synthesized in which the cholestane ring system was replaced by normal alkenyl and phosphodiester substituents having varied chain lengths and lipophilicities. The compounds containing simple alkenyl substituents were found to be more potent as inhibitors of the cytopathic effect of HIV-1 in cell culture than the phosphodiesters. In addition, the potencies of the alkene congeners correlated positively with chain length and lipophilicity of the alkene. The results indicate that the cholestane moiety of cosalane functions as a lipophilic accessory appendage to escort the dichlorodisalicylmethane pharmacophore to a lipid environment.

  DOI：

  10.1021/jm950666h

文献信息

• Correlation of Anti-HIV Potency with Lipophilicity in a Series of Cosalane Analogs Having Normal Alkenyl and Phosphodiester Chains as Cholestane Replacements
  作者：Robert F. Keyes、W. Marek Golebiewski、Mark Cushman

  DOI：10.1021/jm950666h

  日期：1996.1.1

  In order to define the role of the cholestane moiety in the anti-HIV agent cosalane, a series of cosalane analogs was synthesized in which the cholestane ring system was replaced by normal alkenyl and phosphodiester substituents having varied chain lengths and lipophilicities. The compounds containing simple alkenyl substituents were found to be more potent as inhibitors of the cytopathic effect of HIV-1 in cell culture than the phosphodiesters. In addition, the potencies of the alkene congeners correlated positively with chain length and lipophilicity of the alkene. The results indicate that the cholestane moiety of cosalane functions as a lipophilic accessory appendage to escort the dichlorodisalicylmethane pharmacophore to a lipid environment.