4,4-(3',3"-dicarboxy-5',5"-dichloro-4',4"-dihydroxydiphenyl)-3-buten-1-yl hexadecyl phosphate

• 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: 4,4-(3',3"-dicarboxy-5',5"-dichloro-4',4"-dihydroxydiphenyl)-3-buten-1-yl hexadecyl phosphate
• 英文别名: 5-[1-(3-Carboxy-5-chloro-4-hydroxy-phenyl)-4-[hexadecoxy(hydroxy)phosphoryl]oxy-but-1-enyl]-3-chloro-2-hydroxy-benzoic acid；5-[1-(3-carboxy-5-chloro-4-hydroxyphenyl)-4-[hexadecoxy(hydroxy)phosphoryl]oxybut-1-enyl]-3-chloro-2-hydroxybenzoic acid
• 化学式: C₃₄H₄₇Cl₂O₁₀P
• 分子量: 717.621
• InChiKey: PDPNCSTZSVIBGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  47
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  171
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  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 hexadecyl ester 1-methyl-2-oxo-propyl ester 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以62%的产率得到4,4-(3',3"-dicarboxy-5',5"-dichloro-4',4"-dihydroxydiphenyl)-3-buten-1-yl hexadecyl 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

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.