methyl (S)-2-((1R,3R,5R,6R)-6-(benzyloxycarbonylamino)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxamido)propanoate | 1446762-64-6

• 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: methyl (S)-2-((1R,3R,5R,6R)-6-(benzyloxycarbonylamino)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxamido)propanoate
• 英文别名: methyl (2S)-2-[[(1R,3R,6R,7R)-3-methyl-5-oxo-1-phenyl-6-(phenylmethoxycarbonylamino)-7-propan-2-yl-1,2,6,7-tetrahydropyrazolo[1,2-a]pyrazole-3-carbonyl]amino]propanoate
• CAS: 1446762-64-6
• 化学式: C₂₉H₃₆N₄O₆
• 分子量: 536.628
• InChiKey: RBNUNADEDJEWCZ-HZGVYFCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 2-(benzyloxycarbonylamino)-3-isopropylacrylate 在 N-甲基吗啉 、 一水合肼 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 65.08h， 生成 methyl (S)-2-((1R,3R,5R,6R)-6-(benzyloxycarbonylamino)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxamido)propanoate 、 methyl (S)-2-((1S,3S,5S,6S)-6-(benzyloxycarbonylamino)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxamido)propanoate
  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

文献信息

• Synthesis of pyrazolo[1,2-a]pyrazole-based peptide mimetics
  作者：Ana Novak、Ana Testen、Jure Bezenšek、Uroš Grošelj、Martina Hrast、Marta Kasunič、Stanislav Gobec、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tet.2013.05.122

  日期：2013.8

  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.