(S)-1-[(R)-2-((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-hexanoyl]-pyrrolidine-2-carboxylic acid | 345347-08-2

• 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: (S)-1-[(R)-2-((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-hexanoyl]-pyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-[(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]hexanoyl]pyrrolidine-2-carboxylic acid
• CAS: 345347-08-2
• 化学式: C₁₆H₂₅NO₆
• 分子量: 327.378
• InChiKey: BVLUPZQOQYVYMU-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-1-[(R)-2-((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-hexanoyl]-pyrrolidine-2-carboxylic acid 在 羟胺 、 二乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (S)-1-[(R)-2-((S)-Hydroxy-hydroxycarbamoyl-methyl)-hexanoyl]-pyrrolidine-2-carboxylic acid propylamide
  参考文献：
  名称：

  α-Substituted hydroxamic acids as novel bacterial deformylase inhibitor-based antibacterial agents

  摘要：

  We report the synthesis and biological activity of analogues of VRC3375 (N-hydroxy-3-R-butyl-3-[(2-S-(tert-butoxycarbonyl)-pyrrolidin-1-ylcarbonyl]propionamide), an orally active peptide deformylase inhibitor. This study explores the structureactivity relationship of various chelator groups, alpha substituents, P-2' and P-3' substituents in order to achieve optimal antibacterial activity with minimal toxicity liability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.020
• 作为产物：
  描述：

  (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]hexanoic acid 在 palladium on activated charcoal 氢气 、 二乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (S)-1-[(R)-2-((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-hexanoyl]-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  α-Substituted hydroxamic acids as novel bacterial deformylase inhibitor-based antibacterial agents

  摘要：

  We report the synthesis and biological activity of analogues of VRC3375 (N-hydroxy-3-R-butyl-3-[(2-S-(tert-butoxycarbonyl)-pyrrolidin-1-ylcarbonyl]propionamide), an orally active peptide deformylase inhibitor. This study explores the structureactivity relationship of various chelator groups, alpha substituents, P-2' and P-3' substituents in order to achieve optimal antibacterial activity with minimal toxicity liability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.020

文献信息

• α-Substituted hydroxamic acids as novel bacterial deformylase inhibitor-based antibacterial agents
  作者：R. Jain、A. Sundram、S. Lopez、G. Neckermann、C. Wu、C. Hackbarth、D. Chen、W. Wang、N.S. Ryder、B. Weidmann、D. Patel、J. Trias、R. White、Z. Yuan

  DOI：10.1016/j.bmcl.2003.07.020

  日期：2003.12

  We report the synthesis and biological activity of analogues of VRC3375 (N-hydroxy-3-R-butyl-3-[(2-S-(tert-butoxycarbonyl)-pyrrolidin-1-ylcarbonyl]propionamide), an orally active peptide deformylase inhibitor. This study explores the structureactivity relationship of various chelator groups, alpha substituents, P-2' and P-3' substituents in order to achieve optimal antibacterial activity with minimal toxicity liability. (C) 2003 Elsevier Ltd. All rights reserved.