(2R)-2-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2S)-4-methyl-2-[(3R)-3-[(2S)-4-methyl-2-(methylamino)pentanoyl]oxy-2-oxopyrrolidin-1-yl]pentanoyl]oxy-3-phenylpropanoyl]amino]pentanoyl]oxypropanoyl]amino]pentanoyl]oxy-3-phenylpropanoic acid | 188908-85-2

• 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: (2R)-2-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2S)-4-methyl-2-[(3R)-3-[(2S)-4-methyl-2-(methylamino)pentanoyl]oxy-2-oxopyrrolidin-1-yl]pentanoyl]oxy-3-phenylpropanoyl]amino]pentanoyl]oxypropanoyl]amino]pentanoyl]oxy-3-phenylpropanoic acid
• CAS: 188908-85-2
• 化学式: C₅₂H₇₆N₄O₁₃
• 分子量: 965.194
• InChiKey: GXIBZOKNHJLRCG-HGPOTLJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  69
• 可旋转键数：
  31
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  216
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2S)-4-methyl-2-[(3R)-3-[(2S)-4-methyl-2-(methylamino)pentanoyl]oxy-2-oxopyrrolidin-1-yl]pentanoyl]oxy-3-phenylpropanoyl]amino]pentanoyl]oxypropanoyl]amino]pentanoyl]oxy-3-phenylpropanoic acid 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以27%的产率得到(2S,5R,8S,11R,14S,17R,20S,23R)-5,17-Dibenzyl-2,8,14,20-tetraisobutyl-7,11,13,19-tetramethyl-4,10,16,22-tetraoxa-1,7,13,19-tetraaza-bicyclo[21.2.1]hexacosan-3,6,9,12,15,18,21,26-octaone
  参考文献：
  名称：

  Restricted Conformation Analogues of an Anthelmintic Cyclodepsipeptide

  摘要：

  Six analogues of the anthelmintic cyclodepsipeptide PF1022A were prepared, each containing a small ring fused to the macrocycle to restrict the number of conformations the larger ring can adopt. It was anticipated that such conformational changes could lead to enhanced biological activity and selectivity. The analogues form two series of three members each. In one series, a carbon-based molecular bridge joins the methyl of a leucine residue with the methyl of its closest lactic acid residue to form five-, six-, and seven-membered lactam rings. In the second series, a leucine residue is replaced with five-, six-, and seven-membered nitrogen heterocycles. Decreasing the size of the small ring in the lactam. series increasingly distorts the macrocycle and consistently decreases activity relative to PF1022A. In the leucine series, a similar trend is observed. Molecular modeling of PF1022A along with the analogues described herein suggests that the ability to exist in a highly symmetrical conformational state is a necessary condition for biological activity.

  DOI：

  10.1021/jm020482k
• 作为产物：
  描述：

  N-Boc-N-methyl-L-leucyl-D-lactic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.74 kPa 条件下， 反应 15.0h， 生成 (2R)-2-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2S)-4-methyl-2-[(3R)-3-[(2S)-4-methyl-2-(methylamino)pentanoyl]oxy-2-oxopyrrolidin-1-yl]pentanoyl]oxy-3-phenylpropanoyl]amino]pentanoyl]oxypropanoyl]amino]pentanoyl]oxy-3-phenylpropanoic acid
  参考文献：
  名称：

  Restricted Conformation Analogues of an Anthelmintic Cyclodepsipeptide

  摘要：

  Six analogues of the anthelmintic cyclodepsipeptide PF1022A were prepared, each containing a small ring fused to the macrocycle to restrict the number of conformations the larger ring can adopt. It was anticipated that such conformational changes could lead to enhanced biological activity and selectivity. The analogues form two series of three members each. In one series, a carbon-based molecular bridge joins the methyl of a leucine residue with the methyl of its closest lactic acid residue to form five-, six-, and seven-membered lactam rings. In the second series, a leucine residue is replaced with five-, six-, and seven-membered nitrogen heterocycles. Decreasing the size of the small ring in the lactam. series increasingly distorts the macrocycle and consistently decreases activity relative to PF1022A. In the leucine series, a similar trend is observed. Molecular modeling of PF1022A along with the analogues described herein suggests that the ability to exist in a highly symmetrical conformational state is a necessary condition for biological activity.

  DOI：

  10.1021/jm020482k