[(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 | 165336-10-7

• 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: [(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
• CAS: 165336-10-7
• 化学式: C₃₂H₅₈N₄O₅S
• 分子量: 610.902
• InChiKey: FNEHFORNUBHMIE-XQUGMKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸-N-琥珀酰亚胺酯 、 [(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 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以25%的产率得到[(3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-1-[3-[4-(3-acetamidopropylamino)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：

  Sterol−Polyamine Conjugates as Synthetic Ionophores

  摘要：

  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.

  DOI：

  10.1021/ja9812960
• 作为产物：
  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：

文献信息

• Squalamine analogues as potential anti-trypanosomal and anti-leishmanial compounds
  作者：Soghra Khabnadideh、Choon Leei Tan、Simon L Croft、Howard Kendrick、Vanessa Yardley、Ian H Gilbert

  DOI：10.1016/s0960-894x(00)00196-7

  日期：2000.6

  of the novel anti-microbial agent, squalamine. The compounds were then investigated for activity against Trypanosoma brucei, the causative agent of African trypanosomiasis, Trypanosoma cruzi, the causative agent of Chagas disease and Leishmania donovani, the causative agent of visceral leishmaniasis. Several compounds showed in vitro activity, especially against T. brucei and L. donovani. However, one

  本文涉及新型抗微生物剂角鲨胺的各种简化类似物的合成。然后研究了这些化合物对非洲锥虫病的病原体布鲁氏锥虫，南美锥虫病的病原体克鲁格氏锥虫和内脏利什曼病的病原体利什曼原虫donovani的活性。几种化合物显示出体外活性，尤其是针对布鲁氏杆菌和杜氏乳酸杆菌。然而，一种化合物显示出差的体内活性。