5α-3-<3'-<(tert-butyldimethylsilyl)oxy>propylidene>cholestane | 158800-51-2

• 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-3-<3'-<(tert-butyldimethylsilyl)oxy>propylidene>cholestane
• 英文别名: tert-butyl-[(3E)-3-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]propoxy]-dimethylsilane
• CAS: 158800-51-2
• 化学式: C₃₆H₆₆OSi
• 分子量: 543.005
• InChiKey: VVJWFDHAEQMOLK-JPAFFITQSA-N

物化性质

• 沸点：
  556.0±19.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.45
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5α-3-<3'-<(tert-butyldimethylsilyl)oxy>propylidene>cholestane 在 platinum(IV) oxide 四溴化碳 、 四丁基氟化铵 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 5.17h， 生成 5α-3β-(3'-bromopropyl)cholestane
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Cosalane, a Novel Anti-HIV Agent Which Inhibits Multiple Features of Virus Reproduction

  摘要：

  Cosalane (3), a novel anti-HIV agent having a disalicylmethane unit linked to C-3 of cholestane by a three-carbon Linker, was synthesized from commercially available starting materials by a convergent route. Cosalane proved to be a potent inhibitor of HIV with a broad range of activity against a variety of laboratory, drug-resistant, and clinical HIV-1 isolates, HIV-2, and Rauscher murine leukemia virus. The cytotoxicity of cosalane is relatively low as reflected by an in vitro therapeutic index of > 100. Although cosalane inhibits HIV-1 reverse transcriptase and protease, time of addition experiments indicate that it prevents the cytopathic effect of HIV by acting earlier than reverse transcription in the viral replication cycle. The available evidence indicates that the primary mechanism of action of cosalane involves inhibition of gp120-CD4 binding as well as inhibition of a postattachment event prior to reverse transcription.

  DOI：

  10.1021/jm00045a008
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 、 [3-[(tert-butyldimethylsilyl)oxy]propyl]triphenylphosphonium bromide 在 正丁基锂 作用下， 生成 5α-3-<3'-<(tert-butyldimethylsilyl)oxy>propylidene>cholestane
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Cosalane, a Novel Anti-HIV Agent Which Inhibits Multiple Features of Virus Reproduction

  摘要：

  Cosalane (3), a novel anti-HIV agent having a disalicylmethane unit linked to C-3 of cholestane by a three-carbon Linker, was synthesized from commercially available starting materials by a convergent route. Cosalane proved to be a potent inhibitor of HIV with a broad range of activity against a variety of laboratory, drug-resistant, and clinical HIV-1 isolates, HIV-2, and Rauscher murine leukemia virus. The cytotoxicity of cosalane is relatively low as reflected by an in vitro therapeutic index of > 100. Although cosalane inhibits HIV-1 reverse transcriptase and protease, time of addition experiments indicate that it prevents the cytopathic effect of HIV by acting earlier than reverse transcription in the viral replication cycle. The available evidence indicates that the primary mechanism of action of cosalane involves inhibition of gp120-CD4 binding as well as inhibition of a postattachment event prior to reverse transcription.

  DOI：

  10.1021/jm00045a008

文献信息

• Design, Synthesis, and Biological Evaluation of Cosalane, a Novel Anti-HIV Agent Which Inhibits Multiple Features of Virus Reproduction
  作者：Mark Cushman、W. Marek Golebiewski、James B. McMahon、Robert W. Buckheit、David J. Clanton、Owen Weislow、Rudiger D. Haugwitz、John P. Bader、Lisa Graham、William G. Rice

  DOI：10.1021/jm00045a008

  日期：1994.9

  Cosalane (3), a novel anti-HIV agent having a disalicylmethane unit linked to C-3 of cholestane by a three-carbon Linker, was synthesized from commercially available starting materials by a convergent route. Cosalane proved to be a potent inhibitor of HIV with a broad range of activity against a variety of laboratory, drug-resistant, and clinical HIV-1 isolates, HIV-2, and Rauscher murine leukemia virus. The cytotoxicity of cosalane is relatively low as reflected by an in vitro therapeutic index of > 100. Although cosalane inhibits HIV-1 reverse transcriptase and protease, time of addition experiments indicate that it prevents the cytopathic effect of HIV by acting earlier than reverse transcription in the viral replication cycle. The available evidence indicates that the primary mechanism of action of cosalane involves inhibition of gp120-CD4 binding as well as inhibition of a postattachment event prior to reverse transcription.