琥珀酰亚胺基神经酸酯 | 191354-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 琥珀酰亚胺基神经酸酯
• 英文名称: nervonic acid N-hydroxysuccinimide ester
• 英文别名: Succinimidyl Nervonate；(2,5-dioxopyrrolidin-1-yl) (Z)-tetracos-15-enoate
• CAS: 191354-88-8
• 化学式: C₂₈H₄₉NO₄
• 分子量: 463.701
• InChiKey: LMDKSTRSSZZWDK-KTKRTIGZSA-N

物化性质

• 熔点：
  53-54°C
• 沸点：
  545.3±33.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、热乙醇、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  33
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  琥珀酰亚胺基神经酸酯 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.5h， 生成 N-nervonoyl-1-O-triphenylmethyl-3-O-(t-butyldiphenylsilyl) ceramide
  参考文献：
  名称：

  Formation of high-axial-ratio-microstructures from natural and synthetic sphingolipids

  摘要：

  Amphiphiles that form high-axial-ratio-microstructures (HARMs) are being considered as novel materials for controlled release of drugs and other biologically functional molecules. HARMs consisting of tubules, ribbons, solid rods and helices are formed from sphingolipids by addition of water to a solution of amphiphile in DMF. Single molecular species of galactocerebroside (GalCer) containing long unsaturated fatty acid chains or natural GalCer containing mixed-length, non-hydroxy fatty acids (NFA-GalCer) or alpha-hydroxy fatty acids (HFA-GalCer) form cylindrical structures. In contrast, single molecular species of GalCer containing long saturated fatty acids form ribbons and helices. GalCer HARMs are typically under 100 nm in diameter and have lengths of several microns. The importance of the amide of GalCer for HARM formation was evaluated using psychosine, which forms solid fibers, whereas sphingosine and an analog of GalCer in which the amide is reduced to a secondary amine form amorphous aggregates. Single molecular species of ceramide containing long unsaturated fatty acid chains form cylindrical structures, whereas those with long saturated fatty acids form ribbons and helices. Short chain saturated ceramide also forms cylindrical structures. GalCer analogs with N-acetyl-glycine in place of the galactose form fibers whereas those with N-acetyl-proline yield amorphous material. The N-acetyl-proline-containing amphiphile can de doped into pure GalCer or NFA-GalCer without perturbing tubule formation. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00042-x
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 神经酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 以76%的产率得到琥珀酰亚胺基神经酸酯
  参考文献：
  名称：

  Formation of high-axial-ratio-microstructures from natural and synthetic sphingolipids

  摘要：

  Amphiphiles that form high-axial-ratio-microstructures (HARMs) are being considered as novel materials for controlled release of drugs and other biologically functional molecules. HARMs consisting of tubules, ribbons, solid rods and helices are formed from sphingolipids by addition of water to a solution of amphiphile in DMF. Single molecular species of galactocerebroside (GalCer) containing long unsaturated fatty acid chains or natural GalCer containing mixed-length, non-hydroxy fatty acids (NFA-GalCer) or alpha-hydroxy fatty acids (HFA-GalCer) form cylindrical structures. In contrast, single molecular species of GalCer containing long saturated fatty acids form ribbons and helices. GalCer HARMs are typically under 100 nm in diameter and have lengths of several microns. The importance of the amide of GalCer for HARM formation was evaluated using psychosine, which forms solid fibers, whereas sphingosine and an analog of GalCer in which the amide is reduced to a secondary amine form amorphous aggregates. Single molecular species of ceramide containing long unsaturated fatty acid chains form cylindrical structures, whereas those with long saturated fatty acids form ribbons and helices. Short chain saturated ceramide also forms cylindrical structures. GalCer analogs with N-acetyl-glycine in place of the galactose form fibers whereas those with N-acetyl-proline yield amorphous material. The N-acetyl-proline-containing amphiphile can de doped into pure GalCer or NFA-GalCer without perturbing tubule formation. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00042-x

文献信息

• Anti-inflammatory and immunomodulatory amino acid derivatives, their preparation and use
  申请人：——

  公开号：US20040242663A1

  公开（公告）日：2004-12-02

  The present invention ralates to compounds of formula (I): wherein R is hydrogen (H) or C 1-6 alkyl; and X is defined such that —NH—(X)—COOH is the residue of an amino acid, which amino acid may itself optionally be substituted at any pendant amino group thereof by a residue of a carboxylic acid or a derivative thereof; or a salt thereof. The use of these compounds, in particular as potential anti-inflammatory and immunomodulatory drugs, and their preparation are described. 1

  本发明涉及以下式子的化合物（I）： 其中R是氢（H）或C1-6烷基；X的定义是，—NH—（X）—COOH是氨基酸的残基，该氨基酸本身可以在其任何端基氨基上选择性地被羧酸或其衍生物的残基所取代；或其盐。本发明还描述了这些化合物的用途，特别是作为潜在的抗炎和免疫调节药物，以及它们的制备方法。
• ANTI-INFLAMMATORY AND IMMUNOMODULATORY AMINO ACID DERIVATIVES, THEIR PREPARATION AND USE
  申请人：CRODA INTERNATIONAL plc

  公开号：EP1389180A1

  公开（公告）日：2004-02-18
• US6956059B2
  申请人：——

  公开号：US6956059B2

  公开（公告）日：2005-10-18
• [EN] ANTI-INFLAMMATORY AND IMMUNOMODULATORY AMINO ACID DERIVATIVES, THEIR PREPARATION AND USE<br/>[FR] DERIVES D'ACIDES AMINES ANTI-INFLAMMATOIRES ET IMMUNOMODULATEURS, LEUR PREPARATION ET LEUR UTILISATION
  申请人：CRODA INT PLC

  公开号：WO2002094764A1

  公开（公告）日：2002-11-28

  The present invention ralates to compounds of formula (I): wherein R is hydrogen (H) or c1-6 alkyl; and X is defined such that - NH - (X) - COOH is the residue of an amino acid, which amino acid may itself optionally be substituted at any pendant amino group thereof by a residue of a carboxylic acid or a derivative thereof; or a salt thereof. The use of these compounds, in particular as potential anti-inflammatory and immunomodulatory drugs, and their preparation are described.
• Formation of high-axial-ratio-microstructures from natural and synthetic sphingolipids
  作者：Alex S Goldstein、Anatoly N Lukyanov、Paul A Carlson、Paul Yager、Michael H Gelb

  DOI：10.1016/s0009-3084(97)00042-x

  日期：1997.8

  Amphiphiles that form high-axial-ratio-microstructures (HARMs) are being considered as novel materials for controlled release of drugs and other biologically functional molecules. HARMs consisting of tubules, ribbons, solid rods and helices are formed from sphingolipids by addition of water to a solution of amphiphile in DMF. Single molecular species of galactocerebroside (GalCer) containing long unsaturated fatty acid chains or natural GalCer containing mixed-length, non-hydroxy fatty acids (NFA-GalCer) or alpha-hydroxy fatty acids (HFA-GalCer) form cylindrical structures. In contrast, single molecular species of GalCer containing long saturated fatty acids form ribbons and helices. GalCer HARMs are typically under 100 nm in diameter and have lengths of several microns. The importance of the amide of GalCer for HARM formation was evaluated using psychosine, which forms solid fibers, whereas sphingosine and an analog of GalCer in which the amide is reduced to a secondary amine form amorphous aggregates. Single molecular species of ceramide containing long unsaturated fatty acid chains form cylindrical structures, whereas those with long saturated fatty acids form ribbons and helices. Short chain saturated ceramide also forms cylindrical structures. GalCer analogs with N-acetyl-glycine in place of the galactose form fibers whereas those with N-acetyl-proline yield amorphous material. The N-acetyl-proline-containing amphiphile can de doped into pure GalCer or NFA-GalCer without perturbing tubule formation. (C) 1997 Elsevier Science Ireland Ltd.