3,5-dibromo-2-(methoxymethoxy)benzldehyde | 1276560-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-dibromo-2-(methoxymethoxy)benzldehyde
• 英文别名: 3,5-Dibromo-2-(methoxymethoxy)benzaldehyde
• CAS: 1276560-29-2
• 化学式: C₉H₈Br₂O₃
• 分子量: 323.969
• InChiKey: OTLHIHOSJDHRRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dibromo-2-(methoxymethoxy)benzldehyde 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2-(3,5-dibromo-2-(methoxymethoxy)benzyl)isoindoline-1.3-dione
  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
• 作为产物：
  描述：

  3,5-二溴水杨醛 、 氯甲基甲基醚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以93%的产率得到3,5-dibromo-2-(methoxymethoxy)benzldehyde
  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

• [EN] 2,4-DIAMINOPHENOL DERIVATIVE, AND AGENT FOR INHIBITING AGGREGATION OF TAU AND/OR AMYLOID β<br/>[FR] DÉRIVÉ 2,4-DIAMINOPHÉNOL, ET AGENT D'INHIBITION DE L'AGRÉGATION DE TAU ET/OU DE L'AMYLOÏDE β<br/>[JA] ２，４－ジアミノフェノール誘導体、及び、タウ及び／又はアミロイドβの凝集阻害剤
  申请人：THE DOSHISHA

  公开号：WO2017159484A1

  公开（公告）日：2017-09-21

  【課題】タウ及び／又はAβの凝集阻害剤を提供する。 【解決手段】下記式（I）からなる化合物又はその塩である。 この化合物は、タウオパチー及び／又はAβの凝集に起因するアミロイドーシスの治療、診断、症状の軽減及び予防に使用される。