2-[(4S)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylic acid | 1601483-43-5

• 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: 2-[(4S)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylic acid
• CAS: 1601483-43-5
• 化学式: C₁₉H₁₈N₆O₁₁S
• 分子量: 538.452
• InChiKey: ZSPXDBNKZMUCRF-JNHCFAHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  272
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  benzhydryl 2-((S)-4-((Z)-2-((1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydropyridin-2-yl)methoxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetamido)-3-oxoisoxazolidin-2-yl)-5-oxotetrahydrofuran-2-carboxylate 在 三乙基硅烷 、 甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.25h， 以66%的产率得到2-[(4S)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylic acid
  参考文献：
  名称：

  Siderophore Receptor-Mediated Uptake of Lactivicin Analogues in Gram-Negative Bacteria

  摘要：

  Multidrug-resistant Gram-negative pathogens are an emerging threat to human health, and addressing this challenge will require development of new antibacterial agents. This can be achieved through an improved molecular understanding of drugtarget interactions combined with enhanced delivery of these agents to the site of action. Herein we describe the first application of siderophore receptor-mediated drug uptake of lactivicin analogues as a strategy that enables the development of novel antibacterial agents against clinically relevant Gram-negative bacteria. We report the first crystal structures of several sideromimic conjugated compounds bound to penicillin binding proteins PBP3 and PBP1a from Pseudomonas aeruginosa and characterize the reactivity of lactivicin and beta-lactam core structures. Results from drug sensitivity studies with beta-lactamase enzymes are presented, as well as a structure-based hypothesis to reduce susceptibility to this enzyme class. Finally, mechanistic studies demonstrating that sideromimic modification alters the drug uptake process are discussed.

  DOI：

  10.1021/jm500219c