(E)-Octadec-11-enoyl chloride

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (E)-Octadec-11-enoyl chloride
• 英文别名: cis-Vaccenoylchloride
• 化学式: C₁₈H₃₃ClO
• 分子量: 300.912
• InChiKey: WYUXJEJFKYBBMZ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Boc-L-Lys-N1-spermine-Boc3 、 (E)-Octadec-11-enoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Lysine–spermine conjugates: hydrophobic polyamine amides as potent lipopolysaccharide sequestrants

  摘要：

  Lipopolysaccharides (LPS), otherwise termed `endotoxins' are outer-membrane constituents of Gram-negative bacteria. Lipopolysaccharides play a key role in the pathogenesis of `Septic Shock', a major cause of mortality in the critically ill patient. Therapeutic options aimed at limiting downstream systemic inflammatory processes by targeting lipopolysaccharide do not exist at the present time. We have defined the pharmacophore necessary for small molecules to specifically bind and neutralize LPS and, using animal models of sepsis, have shown that the sequestration of circulatory LPS by small molecules is a therapeutically viable strategy. In this paper, the interactions of a focused library of lysine-spermine conjugates with lipopolysaccharide (LPS) have been characterized. Lysine-spermine conjugates with the epsilon-amino terminus of the lysinyl moiety derivatized with long-chain aliphatic hydrophobic substituents in acyl or alkyl linkage bind and neutralize bacterial lipopolysaccharides, and may be of use in the prevention or treatment of endotoxic shock states. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.038

文献信息

• [EN] CHEMICAL COMPOUNDS
  申请人：NORSK HYDRO A.S.

  公开号：WO1993007163A1

  公开（公告）日：1993-04-15

  (EN) New compounds of the general formula (I): Nu-O-Fa, wherein O represents an oxygen, Nu is a nucleoside or nucleoside analogue, and Fa is an acyl group of a mono-unsaturated C18 or 20 fatty acid. The invention also concerns anti viral pharmaceutical and veterinary compositions comprising a compound of formula (I) alone or in combination with a pharmaceutically acceptable carrier.(FR) Nouveaux composés répondant à la formule générale (I): Nu-O-Fa, dans laquelle O représente un oxygène, Nu représente un nucléoside ou un analogue nucléosidique, et Fa représente un groupe acyle d'un acide gras C18-20 mono-insaturé. On a également prévu des compositions pharmaceutiques et vétérinaires comportant un composé de la formule (I) éventuellement associé à un excipient pharmaceutiquement acceptable.

  (EN) 新化合物的一般式(I)：Nu-O-Fa，其中O代表氧原子，Nu为核苷或核苷类似物，Fa为单不饱和C18或C20脂肪酸的酰基。本发明还涉及包含式(I)化合物的抗病毒药物和兽医组合物，可以单独使用或与药用载体组合使用。 (FR) 新化合物的一般式(I)：Nu-O-Fa，其中O代表氧原子，Nu为核苷或核苷类似物，Fa为单不饱和C18或C20脂肪酸的酰基。本发明还涉及包含式(I)化合物的抗病毒药物和兽医组合物，可以单独使用或与药用载体组合使用。
• Diol lipids
  作者：V. A. Vaver、N. V. Prokazova、L. D. Bergel'son

  DOI：10.1007/bf00941671

  日期：——
• CHEMICAL COMPOUNDS
  申请人：NORSK HYDRO A/S

  公开号：EP0642525A1

  公开（公告）日：1995-03-15
• US6548486B1
  申请人：——

  公开号：US6548486B1

  公开（公告）日：2003-04-15
• Lysine–spermine conjugates: hydrophobic polyamine amides as potent lipopolysaccharide sequestrants
  作者：Mark R. Burns、Stewart J. Wood、Kelly A. Miller、Thuan Nguyen、Jens R. Cromer、Sunil A. David

  DOI：10.1016/j.bmc.2005.01.038

  日期：2005.4

  Lipopolysaccharides (LPS), otherwise termed `endotoxins' are outer-membrane constituents of Gram-negative bacteria. Lipopolysaccharides play a key role in the pathogenesis of `Septic Shock', a major cause of mortality in the critically ill patient. Therapeutic options aimed at limiting downstream systemic inflammatory processes by targeting lipopolysaccharide do not exist at the present time. We have defined the pharmacophore necessary for small molecules to specifically bind and neutralize LPS and, using animal models of sepsis, have shown that the sequestration of circulatory LPS by small molecules is a therapeutically viable strategy. In this paper, the interactions of a focused library of lysine-spermine conjugates with lipopolysaccharide (LPS) have been characterized. Lysine-spermine conjugates with the epsilon-amino terminus of the lysinyl moiety derivatized with long-chain aliphatic hydrophobic substituents in acyl or alkyl linkage bind and neutralize bacterial lipopolysaccharides, and may be of use in the prevention or treatment of endotoxic shock states. (c) 2005 Elsevier Ltd. All rights reserved.