3'',3'''-dichloro-5'',5'''-di(methoxycarbonyl)-4'',4'''-di[p-(3-methoxycarbonylphenyl)benzyloxy]-4',4'-diphenyl-3β-(3'-buten-1'-yl)cholestane | 306271-97-6

• 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: 3'',3'''-dichloro-5'',5'''-di(methoxycarbonyl)-4'',4'''-di[p-(3-methoxycarbonylphenyl)benzyloxy]-4',4'-diphenyl-3β-(3'-buten-1'-yl)cholestane
• CAS: 306271-97-6
• 化学式: C₇₇H₈₈Cl₂O₁₀
• 分子量: 1244.45
• InChiKey: BRBPICRURBZDNT-CIJMIFHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.58
• 重原子数：
  89.0
• 可旋转键数：
  22.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3'',3'''-dichloro-5'',5'''-di(methoxycarbonyl)-4'',4'''-di[p-(3-methoxycarbonylphenyl)benzyloxy]-4',4'-diphenyl-3β-(3'-buten-1'-yl)cholestane 在 potassium cyanide 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 22.0h， 以38%的产率得到3'',3'''-dichloro-5'',5'''-dicarboxy-4'',4'''-di[p-(3-carboxyphenyl)benzyloxy]-4',4'-diphenyl-3β-(3'-buten-1'-yl)cholestane
  参考文献：
  名称：

  Correlation of Anti-HIV Activity with Anion Spacing in a Series of Cosalane Analogues with Extended Polycarboxylate Pharmacophores

  摘要：

  Cosalane and its synthetic derivatives inhibit the binding of gp120 to CD4 as well as the fusion of the viral envelope with the cell membrane. The binding of the cosalanes to CD4 is proposed to involve ionic interactions of the negatively charged carboxylates of the ligands with positively charged arginine and lysine amino acid side chains of the protein. To investigate the effect of anion spacing on anti-HIV activity in the cosalane system, a series of cosalane tetracarboxylates was synthesized in which the two proximal and two distal carboxylates are separated by 6-12 atoms. Maximum activity was observed when the proximal and distal carboxylates are separated by 8 atoms. In a series of cosalane amino acid derivatives containing glutamic acid, glycine, aspartic acid, beta -alanine, leucine, and phenylalanine residues, maximum activity was displayed by the di(glutamic acid) analogue. A hypothetical model has been devised for the binding of the cosalane di(glutamic acid) conjugate to CD4. In general, the compounds in this series are more potent against HIV-1(RF) in CEM-SS cells than they are vs HIV-1(IIIB) in MT-4 cells, and they are least potent vs HIV-2(ROD) in MT-4 cells.

  DOI：

  10.1021/jm000290u
• 作为产物：
  描述：

  4-甲苯硼酸 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 palladium dichloride 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 正己烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 27.0h， 生成 3'',3'''-dichloro-5'',5'''-di(methoxycarbonyl)-4'',4'''-di[p-(3-methoxycarbonylphenyl)benzyloxy]-4',4'-diphenyl-3β-(3'-buten-1'-yl)cholestane
  参考文献：
  名称：

  Correlation of Anti-HIV Activity with Anion Spacing in a Series of Cosalane Analogues with Extended Polycarboxylate Pharmacophores

  摘要：

  Cosalane and its synthetic derivatives inhibit the binding of gp120 to CD4 as well as the fusion of the viral envelope with the cell membrane. The binding of the cosalanes to CD4 is proposed to involve ionic interactions of the negatively charged carboxylates of the ligands with positively charged arginine and lysine amino acid side chains of the protein. To investigate the effect of anion spacing on anti-HIV activity in the cosalane system, a series of cosalane tetracarboxylates was synthesized in which the two proximal and two distal carboxylates are separated by 6-12 atoms. Maximum activity was observed when the proximal and distal carboxylates are separated by 8 atoms. In a series of cosalane amino acid derivatives containing glutamic acid, glycine, aspartic acid, beta -alanine, leucine, and phenylalanine residues, maximum activity was displayed by the di(glutamic acid) analogue. A hypothetical model has been devised for the binding of the cosalane di(glutamic acid) conjugate to CD4. In general, the compounds in this series are more potent against HIV-1(RF) in CEM-SS cells than they are vs HIV-1(IIIB) in MT-4 cells, and they are least potent vs HIV-2(ROD) in MT-4 cells.

  DOI：

  10.1021/jm000290u