(R)-2-{(S)-2-[(2-Methyl-3-oxo-octahydro-benzo[1,4]oxazine-2-carbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester | 165114-22-7

• 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: (R)-2-{(S)-2-[(2-Methyl-3-oxo-octahydro-benzo[1,4]oxazine-2-carbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester
• 英文别名: dibenzyl (2R)-2-[[(2S)-2-[(2-methyl-3-oxo-4a,5,6,7,8,8a-hexahydro-4H-benzo[b][1,4]oxazine-2-carbonyl)amino]propanoyl]amino]pentanedioate
• CAS: 165114-22-7
• 化学式: C₃₂H₃₉N₃O₈
• 分子量: 593.677
• InChiKey: HIFIGQVHLJKWGP-FSPKBSCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-{(S)-2-[(2-Methyl-3-oxo-octahydro-benzo[1,4]oxazine-2-carbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到trans-N-(2-Methyl-3-oxo-octahydro-2H-1,4-benzoxazine-2-carbonyl)-L-alanyl-D-glutamic acid
  参考文献：
  名称：

  N-{trans-2-[[2‘-(Acetylamino)cyclohexyl]oxy]acetyl}-l-alanyl-d-glutamic Acid:  A Novel Immunologically Active Carbocyclic Muramyl Dipeptide Analogue

  摘要：

  A novel non-pyrogenic carbocyclic muramyl dipeptide (MDP) analogue, N-(trans-2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl)-L-alanyl-D-glutamic acid, was obtained by replacement of the N-acetylmuramic acid part and the D-isoglutamine residue of the MDP molecule by a trans2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl moiety and D-glutamic acid, respectively. The title compound was selected as a promising candidate for further evaluation among several related analogues on the basis of an immunorestoration test in mice. This novel nor-MDP analogue protects mice against the immunosuppressive effect of cyclophosphamide and increases the nonspecific resistance of mice against fungal infection. It is an immunomodulator which enhances the maturation of lymphocytes B to plasma cells and increases the activity of lymphocytes B and lymphocytes T as well as that of macrophages but does not alter the number of these cells.

  DOI：

  10.1021/jm970509d
• 作为产物：
  描述：

  trans-ethyl-2-methyl-3-oxo-octahydro-2H-1,4-benzoxazine-2-carboxylate 在 sodium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 (R)-2-{(S)-2-[(2-Methyl-3-oxo-octahydro-benzo[1,4]oxazine-2-carbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester
  参考文献：
  名称：

  N-{trans-2-[[2‘-(Acetylamino)cyclohexyl]oxy]acetyl}-l-alanyl-d-glutamic Acid:  A Novel Immunologically Active Carbocyclic Muramyl Dipeptide Analogue

  摘要：

  A novel non-pyrogenic carbocyclic muramyl dipeptide (MDP) analogue, N-(trans-2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl)-L-alanyl-D-glutamic acid, was obtained by replacement of the N-acetylmuramic acid part and the D-isoglutamine residue of the MDP molecule by a trans2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl moiety and D-glutamic acid, respectively. The title compound was selected as a promising candidate for further evaluation among several related analogues on the basis of an immunorestoration test in mice. This novel nor-MDP analogue protects mice against the immunosuppressive effect of cyclophosphamide and increases the nonspecific resistance of mice against fungal infection. It is an immunomodulator which enhances the maturation of lymphocytes B to plasma cells and increases the activity of lymphocytes B and lymphocytes T as well as that of macrophages but does not alter the number of these cells.

  DOI：

  10.1021/jm970509d

文献信息

• <i>N</i>-{<i>trans</i>-2-[[2‘-(Acetylamino)cyclohexyl]oxy]acetyl}-<scp>l</scp>-alanyl-<scp>d</scp>-glutamic Acid:  A Novel Immunologically Active Carbocyclic Muramyl Dipeptide Analogue
  作者：Danijel Kikelj、Slavko Pečar、Vladimir Kotnik、Anton Štalc、Branka Wraber-Herzog、Saša Simčič、Alojz Ihan、Lidija Klamfer、Lučka Povšič、Rok Grahek、Elizabeta Suhadolc、Mirjam Hočevar、Helmut Hönig、Renate Rogi-Kohlenprath

  DOI：10.1021/jm970509d

  日期：1998.2.1

  A novel non-pyrogenic carbocyclic muramyl dipeptide (MDP) analogue, N-(trans-2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl)-L-alanyl-D-glutamic acid, was obtained by replacement of the N-acetylmuramic acid part and the D-isoglutamine residue of the MDP molecule by a trans2-[[2'-(acetylamino)cyclohexyl]oxy]acetyl moiety and D-glutamic acid, respectively. The title compound was selected as a promising candidate for further evaluation among several related analogues on the basis of an immunorestoration test in mice. This novel nor-MDP analogue protects mice against the immunosuppressive effect of cyclophosphamide and increases the nonspecific resistance of mice against fungal infection. It is an immunomodulator which enhances the maturation of lymphocytes B to plasma cells and increases the activity of lymphocytes B and lymphocytes T as well as that of macrophages but does not alter the number of these cells.