2,4-dibromo-6-((2-nitrobenzamido)methyl)phenyl 2-chlorobenzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2,4-dibromo-6-((2-nitrobenzamido)methyl)phenyl 2-chlorobenzoate
• 英文别名: TP-1 Revised；TP-1R；2,4-Dibromo-6-{[(2-nitrobenzene-1-carbonyl)amino]methyl}phenyl benzoate；[2,4-dibromo-6-[[(2-nitrobenzoyl)amino]methyl]phenyl] benzoate
• 化学式: C₂₁H₁₄Br₂N₂O₅
• 分子量: 534.161
• InChiKey: TYMXZAAQZPJROA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(3,5-dibromo-2-(methoxymethoxy)benzyl)-2-nitrobenzamide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 2,4-dibromo-6-((2-nitrobenzamido)methyl)phenyl 2-chlorobenzoate
  参考文献：
  名称：

  Synthesis and Molecular Modeling Provide Insight into a Pseudomonas aeruginosa Quorum Sensing Conundrum

  摘要：

  The triphenyl amide/ester 12 was originally reported to be a potent mimic of the natural 3-oxo-dodecanoyl homoserine lactone quorum sensing molecule in Pseudomonas aeruginosa. However, explicit synthesis/chemical characterization was lacking, and a later report providing protein crystallographic data inferred 12 to be incorrect, with 9 now being the surmised structure. Because of these inconsistencies and our interest in quorum sensing molecules utilized by Gram-negative bacteria, we found it necessary to synthesize 9 and 12 to test for agonistic activity in a P. aeruginosa reporter assay. Despite distinct regiochemical differences, both 9 and 12 were found to have comparable EC(50) values. To reconcile these unanticipated findings, modeling studies were conducted, and both compounds were revealed to have comparable properties for binding to the LasR receptor.

  DOI：

  10.1021/ja111138y

文献信息

• Synthesis and Molecular Modeling Provide Insight into a <i>Pseudomonas aeruginosa</i> Quorum Sensing Conundrum
  作者：Joseph S. Zakhari、Isao Kinoyama、Anjali K. Struss、Prasanna Pullanikat、Colin A. Lowery、Matthew Lardy、Kim D. Janda

  DOI：10.1021/ja111138y

  日期：2011.3.23

  The triphenyl amide/ester 12 was originally reported to be a potent mimic of the natural 3-oxo-dodecanoyl homoserine lactone quorum sensing molecule in Pseudomonas aeruginosa. However, explicit synthesis/chemical characterization was lacking, and a later report providing protein crystallographic data inferred 12 to be incorrect, with 9 now being the surmised structure. Because of these inconsistencies and our interest in quorum sensing molecules utilized by Gram-negative bacteria, we found it necessary to synthesize 9 and 12 to test for agonistic activity in a P. aeruginosa reporter assay. Despite distinct regiochemical differences, both 9 and 12 were found to have comparable EC(50) values. To reconcile these unanticipated findings, modeling studies were conducted, and both compounds were revealed to have comparable properties for binding to the LasR receptor.