N'-hexadecylsulfonyl-1,14-diamino-5,10-diaza-butadecane

• 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: N'-hexadecylsulfonyl-1,14-diamino-5,10-diaza-butadecane
• 英文别名: N-(3-(4-(3-aminopropylamino)butylamino)propyl)hexadecane-1-sulfonamide；N-[3-[4-(3-aminopropylamino)butylamino]propyl]hexadecane-1-sulfonamide
• 化学式: C₂₆H₅₈N₄O₂S
• 分子量: 490.838
• InChiKey: WXJKHYHSCXNLGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  28
• 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

• 作为反应物：
  描述：

  N'-hexadecylsulfonyl-1,14-diamino-5,10-diaza-butadecane 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 N¹-hexadecylsulfonyl-1,14-diamino-5,10-diazabutadecane tris(hydrochloride)
  参考文献：
  名称：

  Polycationic sulfonamides and use thereof

  摘要：

  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。

  公开号：

  US20070287750A1
• 作为产物：
  描述：

  精胺 、 十六烷基磺酰氯 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N'-hexadecylsulfonyl-1,14-diamino-5,10-diaza-butadecane
  参考文献：
  名称：

  Polycationic sulfonamides and use thereof

  摘要：

  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。

  公开号：

  US20070287750A1

文献信息

• Structural correlation between lipophilicity and lipopolysaccharide-sequestering activity in spermine-sulfonamide analogs
  作者：Mark R. Burns、Scott A. Jenkins、Nicolas M. Vermeulen、Rajalakshmi Balakrishna、Thuan B. Nguyen、Matthew R. Kimbrell、Sunil A. David

  DOI：10.1016/j.bmcl.2006.09.026

  日期：2006.12

  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.
• 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.
• 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。
• Polycationic Sulfonamides for the Sequestration of Endotoxin
  作者：Mark R. Burns、Scott A. Jenkins、Matthew R. Kimbrell、Rajalakshmi Balakrishna、Thuan B. Nguyen、Benjamin G. Abbo、Sunil A. David

  DOI：10.1021/jm061198m

  日期：2007.2.1

  Lipopolysaccharides (LPS) play a key role in the pathogenesis of septic shock, a major cause of mortality in the critically ill patient. We had previously shown that monoacylated polyamine compounds specifically bind to and neutralize the activity of LPS with high in vitro potency and afford complete protection in a murine model of endotoxic shock. Fatty acid amides of polyamines may be rapidly cleared from systemic circulation due to their susceptibility to nonspecific serum amidases and, thus, would be predicted to have a short duration of action. In a systematic effort to increase the likelihood of better bioavailability properties together with structural modifications that may result in gains in activity, we now report structure-activity relationships pertaining to endotoxin-binding and -neutralizing activities of homologated polyamine sulfonamides.