(2R,1'S)-2-benzyl-1-benzyloxycarbonyl-2-[(1'-dimethylcarbamoyl)ethyl]carbamoyl azetidine | 1272660-81-7

• 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: (2R,1'S)-2-benzyl-1-benzyloxycarbonyl-2-[(1'-dimethylcarbamoyl)ethyl]carbamoyl azetidine
• 英文别名: benzyl (2R)-2-benzyl-2-[[(1S)-2-(dimethylamino)-1-methyl-2-oxo-ethyl]carbamoyl]azetidine-1-carboxylate；benzyl (2R)-2-benzyl-2-[[(2S)-1-(dimethylamino)-1-oxopropan-2-yl]carbamoyl]azetidine-1-carboxylate
• CAS: 1272660-81-7
• 化学式: C₂₄H₂₉N₃O₄
• 分子量: 423.512
• InChiKey: FFSRLRZFLNGBLZ-UUOWRZLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2RS)-2-benzyl-1-benzyloxycarbonyl-2-carboxylazetidine 、 (S)-2-amino-N,N-dimethylpropanamide trifluoroacetate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(2S,1'S)-2-benzyl-1-benzyloxycarbonyl-2-[(1'-dimethylcarbamoyl)ethyl]carbamoyl azetidine
  参考文献：
  名称：

  Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors

  摘要：

  SAR studies on an azetidine-containing dipeptide prototype inhibitor of HCMV are described. Three series of structurally modified analogues, involving substitutions at the N- and C-terminus, and at the C-terminal side-chain were synthesized and evaluated for antiviral activity. Aliphatic or no substituents at the C-carboxamide group, an aliphatic C-terminal side-chain, as well as a benzyloxycarbonyl moiety at the N-terminus were absolute requirements for anti-HCMV activity. The conformational restriction induced by the 2-azetidine residue into the dipeptide derivatives, identified by H-1 NMR as a gamma-type reverse turn, seems to have influence on the activity of these molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.052

文献信息

• Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors
  作者：Paula Pérez-Faginas、M. Teresa Aranda、M. Teresa García-López、Robert Snoeck、Graciela Andrei、Jan Balzarini、Rosario González-Muñiz

  DOI：10.1016/j.bmc.2010.12.052

  日期：2011.2

  SAR studies on an azetidine-containing dipeptide prototype inhibitor of HCMV are described. Three series of structurally modified analogues, involving substitutions at the N- and C-terminus, and at the C-terminal side-chain were synthesized and evaluated for antiviral activity. Aliphatic or no substituents at the C-carboxamide group, an aliphatic C-terminal side-chain, as well as a benzyloxycarbonyl moiety at the N-terminus were absolute requirements for anti-HCMV activity. The conformational restriction induced by the 2-azetidine residue into the dipeptide derivatives, identified by H-1 NMR as a gamma-type reverse turn, seems to have influence on the activity of these molecules. (C) 2010 Elsevier Ltd. All rights reserved.