(1R,3R,5R,6R)-6-(2-(2-(benzyloxycarbonylamino)acetamido)acetamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylic acid

• 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: (1R,3R,5R,6R)-6-(2-(2-(benzyloxycarbonylamino)acetamido)acetamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylic acid
• 英文别名: (1R,3R,6R,7R)-3-methyl-5-oxo-1-phenyl-6-[[2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]acetyl]amino]-7-propan-2-yl-1,2,6,7-tetrahydropyrazolo[1,2-a]pyrazole-3-carboxylic acid
• 化学式: C₂₉H₃₅N₅O₇
• 分子量: 565.626
• InChiKey: VESAOPUFXIASBA-VKUKUQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,3R,5R,6R)-6-(2-(2-(benzyloxycarbonylamino)acetamido)acetamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylic acid 、 甘氨酰甘氨酸甲酯盐酸盐 在 N-甲基吗啉 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以62%的产率得到methyl 2-(2-((1R,3R,5R,6R)-6-(2-(2-(benzyloxycarbonyl-amino)acetamido)acetamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxamido)acetamido)acetate
  参考文献：
  名称：

  Synthesis of pyrazolo[1,2-a]pyrazole-based peptide mimetics

  摘要：

  The synthesis of U-shaped conformationally constrained analogues of peptides based on the 3-amino-2oxo-1,5-diazabicyclo[3.3.0]octane-8-carboxylic acid scaffold was developed. [3+2] Cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4-benzyloxycarbonylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides to tert-butyl acrylate and tert-butyl methacrylate gave the corresponding racemic cycloadducts, in most cases as mixtures of isomers, which were separated by preparative chromatography. Selective deprotection of the C- and the N-terminal of these heterocyclic dipeptides followed by coupling with (S)-alanine derivatives and chromatographic separation furnished the non-racemic tripeptides as target compounds. The structures of racemic cycloadducts and non-racemic final products were determined by NMR spectroscopy and X-ray diffraction. The synthesized compounds were also evaluated for inhibition of MurD ligase and D-alanine:D-alanine ligase. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.122
• 作为产物：
  描述：

  N-苄氧羰基-甘氨酰-甘氨酸 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1R,3R,5R,6R)-6-(2-(2-(benzyloxycarbonylamino)acetamido)acetamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylic acid
  参考文献：
  名称：

  Synthesis of pyrazolo[1,2-a]pyrazole-based peptide mimetics

  摘要：

  The synthesis of U-shaped conformationally constrained analogues of peptides based on the 3-amino-2oxo-1,5-diazabicyclo[3.3.0]octane-8-carboxylic acid scaffold was developed. [3+2] Cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4-benzyloxycarbonylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides to tert-butyl acrylate and tert-butyl methacrylate gave the corresponding racemic cycloadducts, in most cases as mixtures of isomers, which were separated by preparative chromatography. Selective deprotection of the C- and the N-terminal of these heterocyclic dipeptides followed by coupling with (S)-alanine derivatives and chromatographic separation furnished the non-racemic tripeptides as target compounds. The structures of racemic cycloadducts and non-racemic final products were determined by NMR spectroscopy and X-ray diffraction. The synthesized compounds were also evaluated for inhibition of MurD ligase and D-alanine:D-alanine ligase. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.122