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

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4,4-(3',3''-dicarboxy-5',5''-dichloro-4',4''-dihydroxydiphenyl)-3-buten-1-yl 3-cholestanyl phosphate
• 英文别名: 5-[1-(3-carboxy-5-chloro-4-hydroxy-phenyl)-4-[[(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-hydroxy-phosphoryl]oxy-but-1-enyl]-3-chloro-2-hydroxy-benzoic acid；5-[1-(3-carboxy-5-chloro-4-hydroxyphenyl)-4-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-hydroxyphosphoryl]oxybut-1-enyl]-3-chloro-2-hydroxybenzoic acid
• 化学式: C₄₅H₆₁Cl₂O₁₀P
• 分子量: 863.853
• InChiKey: BATHYLWGHILMGF-PXIIVNOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  58
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 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 (3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl 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41%的产率得到4,4-(3',3''-dicarboxy-5',5''-dichloro-4',4''-dihydroxydiphenyl)-3-buten-1-yl 3-cholestanyl phosphate
  参考文献：
  名称：

  Exploration of the effects of linker chain modifications on anti-HIV activities in a series of cosalane analogues

  摘要：

  The effects of linker chain modifications were investigated in a series of cosalane analogues. The modifications investigated included: (1) shortening the three-carbon linker chain between the dichlorodisalicylmethane and the cholestane moiety by one carbon atom; (2) lengthening the linker chain by one carbon; (3) hydrogenation of the double bond in the linker chain; (4) changing the point of attachment of the linker chain from C-3 to C-6; (5) insertion of a phosphate between the steroid and the linker chain. With the exception of the phosphate modification, which abolished anti-HIV activity and increased cytotoxicity, the linker chain modifications produced relatively minor changes in anti-HIV activity and increased cytotoxicity, the linker chain modifications produced relatively minor changes in anti-HIV potency. The steroid and attached linker chain of cosalane therefore appear only to provide a general lipophilic appendage for the dichlorodisalicylmethane pharmacophore.

  DOI：

  10.1016/0968-0896(96)00159-9

文献信息

• Exploration of the effects of linker chain modifications on anti-HIV activities in a series of cosalane analogues
  作者：W. Marek Golebiewski、Robert F. Keyes、Mark Cushman

  DOI：10.1016/0968-0896(96)00159-9

  日期：1996.10

  The effects of linker chain modifications were investigated in a series of cosalane analogues. The modifications investigated included: (1) shortening the three-carbon linker chain between the dichlorodisalicylmethane and the cholestane moiety by one carbon atom; (2) lengthening the linker chain by one carbon; (3) hydrogenation of the double bond in the linker chain; (4) changing the point of attachment of the linker chain from C-3 to C-6; (5) insertion of a phosphate between the steroid and the linker chain. With the exception of the phosphate modification, which abolished anti-HIV activity and increased cytotoxicity, the linker chain modifications produced relatively minor changes in anti-HIV activity and increased cytotoxicity, the linker chain modifications produced relatively minor changes in anti-HIV potency. The steroid and attached linker chain of cosalane therefore appear only to provide a general lipophilic appendage for the dichlorodisalicylmethane pharmacophore.