O-bis(phenyloxy)phosphoryl N-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine | 253587-43-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-bis(phenyloxy)phosphoryl N-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine
• 英文别名: 4-(diphenyloxyphosphoryloxy)-2-[(R)-3-dodecanoyloxy-tetra-decanoyl-amino]butanoic acid；4-(diphenyloxyphosphoryloxy)-2-[(R)-3-dodecanoyloxytetradecanoylamino]-butanoic acid；4-diphenoxyphosphoryloxy-2-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]butanoic acid
• CAS: 253587-43-8
• 化学式: C₄₂H₆₆NO₉P
• 分子量: 759.961
• InChiKey: WOLIEXWPNGLLGF-SWGHGFEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  53
• 可旋转键数：
  34
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O-bis(phenyloxy)phosphoryl N-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine 在 palladium on activated charcoal 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 O-bis(phenyloxy)phosphoryl N-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine N-{(4R)-5-hydroxy-4-[(R)-3-hydroxytetradecanoylamino]pentyl}amide
  参考文献：
  名称：

  Synthesis and Immunobiological Activity of an Original Series of Acyclic Lipid A Mimics Based on a Pseudodipeptide Backbone

  摘要：

  N-delta-L-Homoserinyl-D-ornithinol pseudodipeptides N-acylated with typical Escherichia coli lipid A fatty acid residues and mono-O- or bis-O-phosphorylated have been prepared and their properties investigated. The derivatives carrying two phosphate groups were found to be inducers of NO production. In addition, while they were unable to induce significantly the production of interleukin-6 (IL-6) by human PBMC cells, these compounds behaved also as potent antagonists of LPS-induced IL-6 production in the same human cells system. In conclusion, the molecules described here are the first members of an original class of immunobiologically active lipid A mimics based on an acyclic pseudodipeptide backbone carrying only the essential functionalities of the parent lipid A structure (OM-174). As the products exhibit very low endotoxicity and pyrogenicity, this class of lipid A mimics therefore opens a new generation of immunoadjuvants that possibly could reach clinical applications.

  DOI：

  10.1021/jm060482a
• 作为产物：
  描述：

  (R)-(-)-3-羟基十四烷酸 在 palladium on activated charcoal N-甲基吗啉 、 吡啶 、 氢气 、 四丁基碘化铵 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 40.5h， 生成 O-bis(phenyloxy)phosphoryl N-[(R)-3-dodecanoyloxytetradecanoyl] DL-homoserine
  参考文献：
  名称：

  Synthesis and Immunobiological Activity of an Original Series of Acyclic Lipid A Mimics Based on a Pseudodipeptide Backbone

  摘要：

  N-delta-L-Homoserinyl-D-ornithinol pseudodipeptides N-acylated with typical Escherichia coli lipid A fatty acid residues and mono-O- or bis-O-phosphorylated have been prepared and their properties investigated. The derivatives carrying two phosphate groups were found to be inducers of NO production. In addition, while they were unable to induce significantly the production of interleukin-6 (IL-6) by human PBMC cells, these compounds behaved also as potent antagonists of LPS-induced IL-6 production in the same human cells system. In conclusion, the molecules described here are the first members of an original class of immunobiologically active lipid A mimics based on an acyclic pseudodipeptide backbone carrying only the essential functionalities of the parent lipid A structure (OM-174). As the products exhibit very low endotoxicity and pyrogenicity, this class of lipid A mimics therefore opens a new generation of immunoadjuvants that possibly could reach clinical applications.

  DOI：

  10.1021/jm060482a

文献信息

• Novel acyl-dipeptide-like compounds, a method for preparing the same and pharmaceutical compositions containing such products
  申请人：Bauer Jacques

  公开号：US20060148678A1

  公开（公告）日：2006-07-06

  The invention relates to the field of chemistry and more specifically to the field of medicinal chemistry. The invention is directed to N-acyl-dipeptide-like compounds having the general formula I wherein substituents A, B, X, Y, R 1 , R 2 , and subscripts n, m, p and q have the same meanings as those given in the claims. The invention is equally directed to pharmaceutical compositions containing as an active ingredient at least one compound of general formula I either in acid or salt form with an organic or mineral base. The compounds persuant to the invention display interesting pharmacological properties which make them useful as drugs.

  这项发明涉及化学领域，更具体地涉及药物化学领域。该发明涉及具有通式I的N-酰基二肽类化合物，其中取代基A、B、X、Y、R1、R2以及下标n、m、p和q的含义与索赔中给出的相同。该发明还涉及含有作为活性成分的至少一种通式I化合物的药物组合物，其以有机或矿物质碱的酸或盐形式存在。根据该发明的化合物展示出有趣的药理特性，使它们可用作药物。
• Novel acyl-dipeptide-like compounds bearing an accessory functional side chain spacer, a method for preparing the same and pharmaceutical compositions containing such products
  申请人：Bauer Jacques

  公开号：US20050192232A1

  公开（公告）日：2005-09-01

  The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants, In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targetting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.

  该发明特别涉及类二肽样化合物，这些化合物源自功能性取代的氨基酸，通过酰胺化作用将脂肪酸链结合到所述类二肽样化合物的氨基官能团上，其中一端部分带有辅助功能侧链间隔物，另一端部分是酸基，可以是中性或带电状态。该发明的化合物具有类似佐剂的免疫调节特性。此外，该发明的化合物可以嫁接到给定抗原上，以调节或调整免疫反应，也可以嫁接到药物载体上，以增强治疗效果或靶向效果。因此，该发明的化合物在人类和兽医医学中均可用作免疫原和诊断工具。
• Acyl pseudodipeptides which carry a functionalised auxialiary arm
  申请人：——

  公开号：US20030203852A1

  公开（公告）日：2003-10-30

  The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants, In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targetting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.

  本发明特别涉及从功能性取代氨基酸衍生的二肽样化合物，其通过酰胺化作用将脂肪酸链结合到所述二肽样化合物的氨基功能团上，其中一端部分带有附属功能侧链间隔物，另一端部分是酸基，可以是中性或带电状态。本发明的化合物具有类似佐剂的免疫调节性质。此外，本发明的化合物可以嫁接到给定抗原上，以调节或调整免疫应答，或者可以嫁接到药物载体上，以增强治疗效果或靶向作用。因此，本发明的化合物在人类和兽医医学中均可用作免疫原和诊断工具。
• ACYL PSEUDOPEPTIDES WHICH CARRY A FUNCTIONALIZED AUXILIARY ARM
  申请人：BAUER Jacques

  公开号：US20130022628A1

  公开（公告）日：2013-01-24

  The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants. In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targeting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.

  本发明特别针对从功能取代的氨基酸中衍生出来的二肽类化合物，其通过酰胺化作用将脂肪酸链结合到所述二肽类化合物的胺基官能团上，其中一端部分具有辅助功能侧链间隔物，而另一端部分是一个酸基，可以是中性或带电状态。本发明的化合物具有类似佐剂的免疫调节特性。此外，本发明的化合物可以嫁接到给定的抗原上，以调节或调整免疫反应，也可以同样嫁接到药物载体上，以增强其治疗效果或靶向性。因此，本发明的化合物在人类和兽医医学中均可用作免疫原和诊断工具。
• Acyl pseudodipeptides, preparation method and pharmaceutical compositions containing same
  申请人：Om Pharma

  公开号：US07157092B1

  公开（公告）日：2007-01-02

  Compounds of the formula wherein the substitutents are defined as in the specification useful for modulating immune responses in warm-blooded animals.

  该公式中的化合物，其中取代基如规范中所定义，对于调节温血动物的免疫反应是有用的。