N¹-(N-octanesulfonyl)-spermine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N¹-(N-octanesulfonyl)-spermine
• 英文别名: N1-n-octanesulfonyl-spermine；N-[3-[4-(3-aminopropylamino)butylamino]propyl]octane-1-sulfonamide
• 化学式: C₁₈H₄₂N₄O₂S
• 分子量: 378.623
• InChiKey: GRBSLVSXBQWUSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  精胺 、 1-辛烷磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N¹-(N-octanesulfonyl)-spermine
  参考文献：
  名称：

  Structural correlation between lipophilicity and lipopolysaccharide-sequestering activity in spermine-sulfonamide analogs

  摘要：

  Lipopolysaccharides (LPS), otherwise termed 'endotoxins', are outer-membrane constituents of Gram-negative bacteria, and play a key role in the pathogenesis of 'Septic Shock', a major cause of mortality in the critically ill patient. We had previously defined the pharmacophore necessary for small molecules to specifically bind and neutralize this complex carbohydrate. A series of aryl and aliphatic spermine-sulfonamide analogs were synthesized and tested in a series of binding and cell-based assays in order to probe the effect of lipophilicity on sequestration ability. A strong correlation was indeed found, supporting the hypothesis that endotoxin-neutralizing ability involves a lipophilic or membrane attachment event. The research discussed herein may be useful for the design of additional carbohydrate recognizing molecules and endotoxin-neutralizing drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.026

文献信息

• Polycationic sulfonamides and use thereof
  申请人：Burns Mark R.

  公开号：US20070287750A1

  公开（公告）日：2007-12-13

  Certain lipophilic polycationic sulfonamides are provided and are useful for treating various diseases or conditions and particularly sepsis.

  提供了某些亲脂性多阳离子磺胺类化合物，可用于治疗各种疾病或症状，尤其是败血症。
• Tetrahydro-beta-carboline compounds and use thereof
  申请人：Burns R. Mark

  公开号：US20050209264A1

  公开（公告）日：2005-09-22

  Tetrahydro-β-carboline compounds represented by the following formulae: wherein x, y and z are each independently an integer of 0 to 4 and R is selected from the group consisting of H, alkyl, aryl and heterocyclic moiety wherein the alkyl, aryl and heterocyclic moiety are optionally substituted with a member selected from the group consisting of halogen, alkoxy and trifluoromethyl; pharmaceutically acceptable salts thereof and prodrugs thereof are provided. The compounds are useful for treating neurological diseases.

  以下公式代表的四氢-β-咔啉类化合物：其中x、y和z分别是0至4的整数，R从H、烷基、芳基和杂环基中选择，其中烷基、芳基和杂环基可以选择性地用来自卤素、烷氧基和三氟甲基的成员替代；提供其药学上可接受的盐和前药。这些化合物可用于治疗神经系统疾病。
• US7232831B2
  申请人：——

  公开号：US7232831B2

  公开（公告）日：2007-06-19
• US7411002B2
  申请人：——

  公开号：US7411002B2

  公开（公告）日：2008-08-12
• [EN] POLYCATIONIC SULFONAMIDES AND USE THEREOF<br/>[FR] SULFONAMIDES POLYCATIONIQUES ET UTILISATION DE CEUX-CI
  申请人：UNIV KANSAS

  公开号：WO2007143735A2

  公开（公告）日：2007-12-13

  [EN] Certain lipophilic polycationic sulfonamides are provided and are useful for treating various diseases or conditions and particularly sepsis.
  [FR] La présente invention concerne certains sulfonamides polycationiques utiles pour traiter différentes maladies ou pathologies et particulièrement la sepsie.