5α-3β-<4,4-(3',3''-dicarboxy-5',5''-dichloro-4',4''-bis(m-nitrobenzyloxy)diphenyl)buten-3-yl>cholestane

• 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: 5α-3β-<4,4-(3',3''-dicarboxy-5',5''-dichloro-4',4''-bis(m-nitrobenzyloxy)diphenyl)buten-3-yl>cholestane
• 英文别名: 5-[1-[3-carboxy-5-chloro-4-[(3-nitrophenyl)methoxy]phenyl]-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]but-1-enyl]-3-chloro-2-[(3-nitrophenyl)methoxy]benzoic acid
• 化学式: C₅₉H₇₀Cl₂N₂O₁₀
• 分子量: 1038.12
• InChiKey: HXPCIMGTAJWCAS-AMUMGBCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.7
• 重原子数：
  73
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  铵5-[(Z)-1-(3-羧基-5-氯-4-羟基苯基)-4-[(3S,10S,13R,17R)-10,13-二甲基-17-(6-甲基庚烷-2-基)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-3-基]丁-1-烯基]-3-氯-2-羟基苯甲酸酯 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5α-3β-<4,4-(3',3''-dicarboxy-5',5''-dichloro-4',4''-bis(m-nitrobenzyloxy)diphenyl)buten-3-yl>cholestane
  参考文献：
  名称：

  Extension of the Polyanionic Cosalane Pharmacophore as a Strategy for Increasing Anti-HIV Potency

  摘要：

  The anti-HIV agent cosalane inhibits both the binding of gp120 to CD4 as well as an undefined postattachment event prior to reverse transcription. Several cosalane analogues having an extended polyanionic "pharmacophore" were designed based on a hypothetical model of the binding of cosalane to CD4. The analogues were synthesized, and a number of them displayed anti-HIV activity. One of the new analogues was found to possess enhanced potency as an anti-HIV agent relative to cosalane itself. Although the new analogues inhibited both HIV-1 and HTV-2, they were more potent as inhibitors of HIV-1 than HIV-2. Mechanism of action studies indicated that the most potent of the new analogues inhibited fusion of the viral envelope with the cell membrane at lower concentrations than it inhibited attachment, suggesting inhibition of fusion as the primary mechanism of action.

  DOI：

  10.1021/jm980727m

文献信息

• Extension of the Polyanionic Cosalane Pharmacophore as a Strategy for Increasing Anti-HIV Potency
  作者：Mark Cushman、Shabana Insaf、Gitendra Paul、Jeffrey A. Ruell、Erik De Clercq、Dominique Schols、Christophe Pannecouque、Myriam Witvrouw、Catherine A. Schaeffer、Jim A. Turpin、Karen Williamson、William G. Rice

  DOI：10.1021/jm980727m

  日期：1999.5.1

  The anti-HIV agent cosalane inhibits both the binding of gp120 to CD4 as well as an undefined postattachment event prior to reverse transcription. Several cosalane analogues having an extended polyanionic "pharmacophore" were designed based on a hypothetical model of the binding of cosalane to CD4. The analogues were synthesized, and a number of them displayed anti-HIV activity. One of the new analogues was found to possess enhanced potency as an anti-HIV agent relative to cosalane itself. Although the new analogues inhibited both HIV-1 and HTV-2, they were more potent as inhibitors of HIV-1 than HIV-2. Mechanism of action studies indicated that the most potent of the new analogues inhibited fusion of the viral envelope with the cell membrane at lower concentrations than it inhibited attachment, suggesting inhibition of fusion as the primary mechanism of action.