N-(1-(N-hydroxycarbamoyl)(1S,2R)-2-hydroxypropyl)[4-(4-phenylbuta-1,3-diynyl)phenyl]carboxamide | 728865-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-(N-hydroxycarbamoyl)(1S,2R)-2-hydroxypropyl)[4-(4-phenylbuta-1,3-diynyl)phenyl]carboxamide
• 英文别名: N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-(phenylbuta-1,3-diynyl)benzamide；N-[(1s,2r)-2-Hydroxy-1-(Hydroxycarbamoyl)propyl]-4-(4-Phenylbuta-1,3-Diyn-1-Yl)benzamide；N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-(4-phenylbuta-1,3-diynyl)benzamide
• CAS: 728865-26-7
• 化学式: C₂₁H₁₈N₂O₄
• 分子量: 362.385
• InChiKey: VUYMSCCEGRLBAF-BEFAXECRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (2S,3R)-3-hydroxy-2-[[4-(4-phenylbuta-1,3-diynyl)benzoyl]amino]butanoate 在 羟胺 作用下， 生成 N-(1-(N-hydroxycarbamoyl)(1S,2R)-2-hydroxypropyl)[4-(4-phenylbuta-1,3-diynyl)phenyl]carboxamide
  参考文献：
  名称：

  Species-Specific and Inhibitor-Dependent Conformations of LpxC: Implications for Antibiotic Design

  摘要：

  LpxC is an essential enzyme in the lipid A biosynthetic pathway in gram-negative bacteria. Several promising antimicrobial lead compounds targeting LpxC have been reported, though they typically display a large variation in potency against different gram-negative pathogens. We report that inhibitors with a diacetylene scaffold effectively overcome the resistance caused by sequence variation in the LpxC substrate-binding passage. Compound binding is captured in complex with representative LpxC orthologs, and structural analysis reveals large conformational differences that mostly reflect inherent molecular features of distinct LpxC orthologs, whereas ligand-induced structural adaptations occur at a smaller scale. These observations highlight the need for a molecular understanding of inherent structural features and conformational plasticity of LpxC enzymes for optimizing LpxC inhibitors as broad-spectrum antibiotics against gram-negative infections.

  DOI：

  10.1016/j.chembiol.2010.11.011

文献信息

• ANTIBACTERIAL AGENTS
  申请人：Andersen Niels H.

  公开号：US20080269221A1

  公开（公告）日：2008-10-30

  Antibacterial compounds of formula I are provided: As well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供化学式I的抗菌化合物：以及立体异构体，药学上可接受的盐，酯和前药; 包含这些化合物的制药组合物; 通过给予这些化合物的途径治疗细菌感染的方法; 以及制备这些化合物的工艺。
• ETHYNYLBENZENE DERIVATIVES
  申请人：Zhou Pei

  公开号：US20130231323A1

  公开（公告）日：2013-09-05

  Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R 1 , R 2 , R 3 , R 101 , L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.

  本发明涉及式(I)、(II)和(II)I的化合物及其药学上可接受的盐，其中变量R、R1、R2、R3、R101、L、D、Q、Y、X和Z的定义如下。这些化合物可用于治疗革兰氏阴性菌感染。
• Antibacterial Agents
  申请人：Andersen Niels H.

  公开号：US20100324025A1

  公开（公告）日：2010-12-23

  Antibacterial compounds of formula I are provided: As well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供公式I的抗菌化合物：以及其对映异构体，药学上可接受的盐，酯和前药；包含这些化合物的制药组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。
• Antibacterial agents
  申请人：The University of Washington

  公开号：EP2295402B1

  公开（公告）日：2015-08-12
• Ethynylbenzene Derivatives
  申请人：Duke University

  公开号：US20170349544A1

  公开（公告）日：2017-12-07

  Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R 1 , R 2 , R 3 , R 101 , L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.