5α,3β-[4',4'-(3",3"-bis[3'''-methoxy-4'''-methoxycarbonylbenzamido]-4",4"-dimethoxy-5",5"-dimethoxycarbonyldiphenyl)-3'-butenyl]cholestane | 244262-75-7

• 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"-bis[3'''-methoxy-4'''-methoxycarbonylbenzamido]-4",4"-dimethoxy-5",5"-dimethoxycarbonyldiphenyl)-3'-butenyl]cholestane
• 英文别名: N-[5-[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]-1-[3-[[hydroxy-(4-methoxy-3-methoxycarbonylphenyl)methylidene]amino]-4-methoxy-5-methoxycarbonylphenyl]but-1-enyl]-2-methoxy-3-methoxycarbonylphenyl]-4-methoxy-3-methoxycarbonylbenzenecarboximidic acid
• CAS: 244262-75-7
• 化学式: C₆₉H₈₈N₂O₁₄
• 分子量: 1169.46
• InChiKey: UQCXXIYRFPRRSE-AOAPFGQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  85
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  200
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5α,3β-[4',4'-(3",3"-bis[3'''-methoxy-4'''-methoxycarbonylbenzamido]-4",4"-dimethoxy-5",5"-dimethoxycarbonyldiphenyl)-3'-butenyl]cholestane 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到5α,3β-4',4'-[3",3"-bis[(3'''-carboxy-4'''-methoxybenzamido)-5",5"-dicarboxy-4",4"-dimethoxydiphenyl]-3'-butenyl]cholestane
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of Cosalane Analogues with Substituted Benzoic Acid Rings Attached to the Pharmacophore through Methylene and Amide Linkers

  摘要：

  The cosalane pharmacophore has been extended by the attachment of two additional substituted benzoic acid rings through amide and methylene linkers. The resulting compounds display significant antiviral activity when tested in vitro for inhibition of the cytopathic effects of HIV-1(RF) in CEM-SS cells and HIV-1(IIIB) in MT-4 cells. The compound containing the methylene linker also shows moderate activity versus HIV-2(ROD) in MT-4 cells. Because cosalane and related compounds containing extended pharmacophores inhibit the binding of gp120 to CD4, the presently described new compounds are assumed to act by a similar mechanism. A hypothetical model is proposed for the binding of the methylene-linked compound to CD4.

  DOI：

  10.1021/jo990177f
• 作为产物：
  描述：

  5α-3β-(3'-hydroxypropyl)cholestane 在 四氯化钛 、 pyridinium chlorochromate 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 5α,3β-[4',4'-(3",3"-bis[3'''-methoxy-4'''-methoxycarbonylbenzamido]-4",4"-dimethoxy-5",5"-dimethoxycarbonyldiphenyl)-3'-butenyl]cholestane
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of Cosalane Analogues with Substituted Benzoic Acid Rings Attached to the Pharmacophore through Methylene and Amide Linkers

  摘要：

  The cosalane pharmacophore has been extended by the attachment of two additional substituted benzoic acid rings through amide and methylene linkers. The resulting compounds display significant antiviral activity when tested in vitro for inhibition of the cytopathic effects of HIV-1(RF) in CEM-SS cells and HIV-1(IIIB) in MT-4 cells. The compound containing the methylene linker also shows moderate activity versus HIV-2(ROD) in MT-4 cells. Because cosalane and related compounds containing extended pharmacophores inhibit the binding of gp120 to CD4, the presently described new compounds are assumed to act by a similar mechanism. A hypothetical model is proposed for the binding of the methylene-linked compound to CD4.

  DOI：

  10.1021/jo990177f

文献信息

• Synthesis and Anti-HIV Activity of Cosalane Analogues with Substituted Benzoic Acid Rings Attached to the Pharmacophore through Methylene and Amide Linkers
  作者：Jeffrey A. Ruell、Erik De Clercq、Christophe Pannecouque、Myriam Witvrouw、Tracy L. Stup、Jim A. Turpin、Robert W. Buckheit,、Mark Cushman

  DOI：10.1021/jo990177f

  日期：1999.8.1

  The cosalane pharmacophore has been extended by the attachment of two additional substituted benzoic acid rings through amide and methylene linkers. The resulting compounds display significant antiviral activity when tested in vitro for inhibition of the cytopathic effects of HIV-1(RF) in CEM-SS cells and HIV-1(IIIB) in MT-4 cells. The compound containing the methylene linker also shows moderate activity versus HIV-2(ROD) in MT-4 cells. Because cosalane and related compounds containing extended pharmacophores inhibit the binding of gp120 to CD4, the presently described new compounds are assumed to act by a similar mechanism. A hypothetical model is proposed for the binding of the methylene-linked compound to CD4.