methyl 3-(S)-n-butyl-3-[2-(S)-carboxypyrrolidin-1-yl-carbonyl)-2-(S)-fluoropropionate | 345347-22-0

• 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 3-(S)-n-butyl-3-[2-(S)-carboxypyrrolidin-1-yl-carbonyl)-2-(S)-fluoropropionate
• 英文别名: (2S)-1-[(2S)-2-[(1S)-1-fluoro-2-methoxy-2-oxoethyl]hexanoyl]pyrrolidine-2-carboxylic acid
• CAS: 345347-22-0
• 化学式: C₁₄H₂₂FNO₅
• 分子量: 303.331
• InChiKey: MUPZQVRNQJQFAE-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-(S)-n-butyl-3-[2-(S)-carboxypyrrolidin-1-yl-carbonyl)-2-(S)-fluoropropionate 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 16.0h， 生成 N-hydroxy-3-(S)-(n-butyl)-3-[2-(S)-((n-propyl)aminocarbonyl)pyrrolidin-1-carbonyl]-2-(S)-fluoropropionamide
  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：

  methyl 3-(R)-n-butyl-3-[2-(S)-tert-butoxycarbonylpyrrolidin-1-yl-carbonyl)-2-(S)-hydroxypropionate 在 吡啶 、 tri(dimethylamino)sulfur(trimethylsilyl) difluoride 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 28.0h， 生成 methyl 3-(S)-n-butyl-3-[2-(S)-carboxypyrrolidin-1-yl-carbonyl)-2-(S)-fluoropropionate
  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

• Novel succinate compounds, compositions and methods of use and preparation
  申请人：——

  公开号：US20020115863A1

  公开（公告）日：2002-08-22

  Novel hydroxamic acid compounds are disclosed. These hydroxamates inhibit peptidyl deformylase (PDF), an enzyme present in prokaryotes. The hydroxymates are useful as antimicrobials and antibiotics. The compounds of the invention display selective inhibition of peptidyl deformylase versus other metalloproteinases such as matrix metalloproteinases (MMPs). Methods of synthesis and of use of the compounds are also disclosed.

  本发明涉及新型羟肟酸化合物。这些羟肟酸衍生物抑制存在于原核生物中的肽变形酶（PDF）酶。这些羟肟酸衍生物可用作抗微生物和抗生素。本发明的化合物对肽变形酶具有选择性抑制作用，而对其他金属蛋白酶如基质金属蛋白酶（MMPs）则没有抑制作用。本发明还公开了化合物的合成方法和使用方法。
• Succinate compounds, compositions and methods of use and preparation
  申请人：Vicuron Pharmaceuticals Inc.

  公开号：US06797820B2

  公开（公告）日：2004-09-28

  Novel hydroxamic acid compounds are disclosed. These hydroxamates inhibit peptidyl deformylase (PDF), an enzyme present in prokaryotes. The hydroxymates are useful as antimicrobials and antibiotics. The compounds of the invention display selective inhibition of peptidyl deformylase versus other metalloproteinases such as matrix metalloproteinases (MMPs). Methods of synthesis and of use of the compounds are also disclosed.

  本发明揭示了新型羟肟酸化合物。这些羟肟酸盐抑制蛋白酶酰基去形成酶（PDF），该酶存在于原核生物中。这些羟肟酸盐可用作抗微生物和抗生素。本发明的化合物在选择性抑制蛋白酶酰基去形成酶方面优于其他金属蛋白酶如基质金属蛋白酶（MMPs）。本发明还揭示了该化合物的合成和使用方法。
• 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.