(2R)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide | 1289626-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide
• 英文别名: (2R)-2-methyl-2-methylsulfonyl-N-(oxan-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide
• CAS: 1289626-41-0
• 化学式: C₂₃H₃₆BNO₇S
• 分子量: 481.418
• InChiKey: PWVWXJFOTNBRKQ-LEQGEALCSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 4'-[(3R)-4-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-4-oxobutyl]biphenyl-4-carboxylic acid
  参考文献：
  名称：

  Potent Inhibitors of LpxC for the Treatment of Gram-Negative Infections

  摘要：

  In this paper, we present the synthesis and SAR as well as selectivity, pharmacokinetic, and infection model data for representative analogues of a novel series of potent antibacterial LpxC inhibitors represented by hydroxamic acid 1a.

  DOI：

  10.1021/jm2014748
• 作为产物：
  描述：

  (2R)-4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acid 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (2R)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide
  参考文献：
  名称：

  Potent Inhibitors of LpxC for the Treatment of Gram-Negative Infections

  摘要：

  In this paper, we present the synthesis and SAR as well as selectivity, pharmacokinetic, and infection model data for representative analogues of a novel series of potent antibacterial LpxC inhibitors represented by hydroxamic acid 1a.

  DOI：

  10.1021/jm2014748

文献信息

• C-Linked Hydroxamic Acid Derivatives Useful As Antibacterial Agents
  申请人：Brown Matthew Frank

  公开号：US20120202777A1

  公开（公告）日：2012-08-09

  The present invention is directed to a new class of hydroxamic acid derivatives of Formula I, wherein the variables G, T, D, L, A, X, R 1 and R 2 are as described hereinabove, and their use as LpxC inhibitors, and more specifically their use to treat bacterial infections.

  本发明涉及一种新的羟肟酸衍生物类别，其化学式为I，其中变量G、T、D、L、A、X、R1和R2如上所述，并且它们作为LpxC抑制剂的用途，更具体地用于治疗细菌感染。
• C-linked hydroxamic acid derivatives useful as antibacterial agents
  申请人：Brown Matthew Frank

  公开号：US08853258B2

  公开（公告）日：2014-10-07

  The present invention is directed to a new class of hydroxamic acid derivatives of Formula I, wherein the variables G, T, D, L, A, X, R1 and R2 are as described hereinabove, and their use as LpxC inhibitors, and more specifically their use to treat bacterial infections.

  本发明涉及一种新的羟肟酸衍生物类别，其化学式为I，其中变量G、T、D、L、A、X、R1和R2如上所述，并且它们作为LpxC抑制剂的用途，更具体地说，它们用于治疗细菌感染。
• [EN] C-LINKED HYDROXAMIC ACID DERIVATIVES USEFUL AS ANTIBACTERIAL AGENTS<br/>[FR] DÉRIVÉS D'ACIDE HYDROXAMIQUE À LIAISON C UTILES COMME AGENTS ANTIBACTÉRIENS
  申请人：PFIZER

  公开号：WO2011045703A3

  公开（公告）日：2011-06-16
• Potent Inhibitors of LpxC for the Treatment of Gram-Negative Infections
  作者：Matthew F. Brown、Usa Reilly、Joseph A. Abramite、Joel T. Arcari、Robert Oliver、Rose A. Barham、Ye Che、Jinshan Michael Chen、Elizabeth M. Collantes、Seung Won Chung、Charlene Desbonnet、Jonathan Doty、Matthew Doroski、Juntyma J. Engtrakul、Thomas M. Harris、Michael Huband、John D. Knafels、Karen L. Leach、Shenping Liu、Anthony Marfat、Andrea Marra、Eric McElroy、Michael Melnick、Carol A. Menard、Justin I. Montgomery、Lisa Mullins、Mark. C. Noe、John O’Donnell、Joseph Penzien、Mark S. Plummer、Loren M. Price、Veerabahu Shanmugasundaram、Christy Thoma、Daniel P. Uccello、Joseph S. Warmus、Donn G. Wishka

  DOI：10.1021/jm2014748

  日期：2012.1.26

  In this paper, we present the synthesis and SAR as well as selectivity, pharmacokinetic, and infection model data for representative analogues of a novel series of potent antibacterial LpxC inhibitors represented by hydroxamic acid 1a.