3β-hydroxybisnor-5-cholenic acid N-succinimidyl ester | 165336-12-9

• 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: 3β-hydroxybisnor-5-cholenic acid N-succinimidyl ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoate
• CAS: 165336-12-9
• 化学式: C₂₆H₃₇NO₅
• 分子量: 443.583
• InChiKey: MEYMMMBMZGZCQS-XJOAOJKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxybisnor-5-cholenic acid N-succinimidyl ester 在 pyridine-SO3 complex 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 [(3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-1-[3-[4-(3-aminopropylamino)butylamino]propylamino]-1-oxopropan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
  参考文献：
  名称：

  Kikuchi, Ken; Bernard, Edward M.; Sadownik, Andrzej, Antimicrobial Agents and Chemotherapy, 1997, vol. 41, # 7, p. 1433 - 1438

  摘要：

  DOI：
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 hydroxybisnorcholenic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 3β-hydroxybisnor-5-cholenic acid N-succinimidyl ester
  参考文献：
  名称：

  Kikuchi, Ken; Bernard, Edward M.; Sadownik, Andrzej, Antimicrobial Agents and Chemotherapy, 1997, vol. 41, # 7, p. 1433 - 1438

  摘要：

  DOI：

文献信息

• Sterol−Polyamine Conjugates as Synthetic Ionophores
  作者：Manette Merritt、Marion Lanier、Gang Deng、Steven L. Regen

  DOI：10.1021/ja9812960

  日期：1998.8.1

  A design principle has been devised for the construction of sterol-polyamine conjugates that function as synthetic ionophores. For feasibility studies, a prototype (1) was synthesized from 3 beta-hydroxybisnor-5-cholenic acid via sequential activation of its carboxylic acid moiety, condensation with spermine, and sulfation of the 3 beta-hydroxyl group. Closely related analogues were also prepared in which the terminal amine group was acetylated (2), the 3 beta-hydroxyl group was left unsulfated (3), and each of the two remaining secondary amines was replaced with oxygen atoms (4). Incorporation of each conjugate into egg phosphatidylglycerol-based vesicles showed that 1 functions as an ionophore by discharging a pH difference across the vesicle membrane, but that 2, 3, and 4 do not. A kinetic analysis of the ionophoric activity of 1 has provided evidence that the majority of the conjugate exists as membrane-bound monomer and that dimers are the active species that are responsible for ion transport. Comparative experiments have also shown that 1 exhibits greater activity in negatively charged phospholipid membranes relative to ones that are electrically neutral. The implications of these findings, with regard to the design of new classes of antibacterial agents, are briefly discussed.