5α-3β,17β-bis[3',3'-bis(3''-carboxy-5''-chloro-4''-hydroxyphenyl)-2'-propenyl]androstane

• 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,17β-bis[3',3'-bis(3''-carboxy-5''-chloro-4''-hydroxyphenyl)-2'-propenyl]androstane
• 英文别名: 5-[3-[(3R,5S,8S,9S,10S,13R,14S,17R)-17-[3,3-bis(3-carboxy-5-chloro-4-hydroxyphenyl)prop-2-enyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-1-(3-carboxy-5-chloro-4-hydroxyphenyl)prop-1-enyl]-3-chloro-2-hydroxybenzoic acid
• 化学式: C₅₃H₅₂Cl₄O₁₂
• 分子量: 1022.8
• InChiKey: NUOYBITXTGVCQP-LTUPVHBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  69
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  230
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  5α-3,17-bis(carboxymethylidene)androstane 在 palladium on activated charcoal tetrachlorobis(tetrahydrofuran)titanium(IV) 、 三溴化硼-二甲基硫醚 三溴甲基硫化硼 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 丙酮 、 甲苯 为溶剂， 反应 85.5h， 生成 5α-3β,17β-bis[3',3'-bis(3''-carboxy-5''-chloro-4''-hydroxyphenyl)-2'-propenyl]androstane
  参考文献：
  名称：

  Synthesis and anti-HIV activity of cosalane analogues incorporating two dichlorodisalicylmethane pharmacophore fragments

  摘要：

  A new series of cosalane analogues incorporating two fragments of the dichlorodisalicylmethane pharmacophore has been synthesized. In order to identify the position for the attachment of the pharmacophore fragments to the steroid ring that results in the most potent analogues, two types of compounds were designed. In the first type, the two pharmacophore fragments were attached at C-3 and C-17 of the steroid ring by using appropriate linker units. In the second type, both pharmacophore groups were connected to C-3 of the steroid through an alkenyl chain containing an amide moiety. All of the new compounds displayed antiviral activity versus HIV-1(RF), HIV-1(IIIB), and HIV-2(ROD) in cell culture. The relative potencies of the compounds resulting from the two attachment strategies were found to depend on the viral strain as well as the cell type, Overall, the attachment of the second pharmacophore did not result in either a large gain or a large loss in anti-HIV activity, and the results are therefore consistent with the hypothesis that the two pharmacophores act independently, and one at a time, with positively charged amino acid side chains present on the surface of gp120 and CD4. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00152-3