(R)-4-Carbamoyl-4-{(S)-2-[2-(2-hexanoylamino-cyclohexyloxy)-acetylamino]-propionylamino}-butyric acid benzyl ester | 201684-43-7

• 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)-4-Carbamoyl-4-{(S)-2-[2-(2-hexanoylamino-cyclohexyloxy)-acetylamino]-propionylamino}-butyric acid benzyl ester
• 英文别名: benzyl (4R)-5-amino-4-[[(2S)-2-[[2-[2-(hexanoylamino)cyclohexyl]oxyacetyl]amino]propanoyl]amino]-5-oxopentanoate
• CAS: 201684-43-7
• 化学式: C₂₉H₄₄N₄O₇
• 分子量: 560.691
• InChiKey: LEJCSFCPONMDCL-QIMTYXLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  40
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-4-Carbamoyl-4-{(S)-2-[2-(2-hexanoylamino-cyclohexyloxy)-acetylamino]-propionylamino}-butyric acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到(R)-4-Carbamoyl-4-{(S)-2-[2-(2-hexanoylamino-cyclohexyloxy)-acetylamino]-propionylamino}-butyric 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：

  benzyl (4R)-5-amino-4-[[(2S)-2-[[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]oxyacetyl]amino]propanoyl]amino]-5-oxopentanoate 在 盐酸 、 叠氮磷酸二苯酯 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 (R)-4-Carbamoyl-4-{(S)-2-[2-(2-hexanoylamino-cyclohexyloxy)-acetylamino]-propionylamino}-butyric acid benzyl 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.