3-amino-5-(3-methoxyphenyl)-1,3-dihydrobenzo[e][1,4]diazepin-2-one | 376584-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 3-amino-5-(3-methoxyphenyl)-1,3-dihydrobenzo[e][1,4]diazepin-2-one
• 英文别名: 3-Amino-5-(3-methoxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one
• CAS: 376584-84-8
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: VMKPILYKAKCTIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-5-(3-methoxyphenyl)-1,3-dihydrobenzo[e][1,4]diazepin-2-one 、 甲氧基苯甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以41%的产率得到2-methoxy-N-[5-(3-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl]-benzamide
  参考文献：
  名称：

  1,4-Benzodiazepines as Inhibitors of Respiratory Syncytial Virus

  摘要：

  Respiratory syncytial virus (RSV) is the cause of one-fifth of all lower respiratory tract infections worldwide and is increasingly being recognized as a serious threat to patient groups with poorly functioning immune systems. Our approach to finding a novel inhibitor of this virus was to screen a 20 000-member diverse library in a whole cell XTT assay. Parallel assays were carried out in the absence of virus in order to quantify any associated cell toxicity. This identified 100 compounds with IC50's less than 50 mu M. A-33903 (18), a 1,4-benzodiazepine analogue, was chosen as the starting point for lead optimization. This molecule was moderately active and demonstrated good pharmacokinetic properties. The most potent compounds identified from this work were A-58568 (47), A-58569 (44), and A-62066 (46), where modifications to the aromatic substitution enhanced potency, and A-58175 (42), where the amide linker was modified.

  DOI：

  10.1021/jm051185t
• 作为产物：
  描述：

  (2-氨基苯基)(3-甲氧基苯基)甲酮 在 N-甲基吗啉 、 氨 、 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.5h， 生成 3-amino-5-(3-methoxyphenyl)-1,3-dihydrobenzo[e][1,4]diazepin-2-one
  参考文献：
  名称：

  1,4-Benzodiazepines as Inhibitors of Respiratory Syncytial Virus

  摘要：

  Respiratory syncytial virus (RSV) is the cause of one-fifth of all lower respiratory tract infections worldwide and is increasingly being recognized as a serious threat to patient groups with poorly functioning immune systems. Our approach to finding a novel inhibitor of this virus was to screen a 20 000-member diverse library in a whole cell XTT assay. Parallel assays were carried out in the absence of virus in order to quantify any associated cell toxicity. This identified 100 compounds with IC50's less than 50 mu M. A-33903 (18), a 1,4-benzodiazepine analogue, was chosen as the starting point for lead optimization. This molecule was moderately active and demonstrated good pharmacokinetic properties. The most potent compounds identified from this work were A-58568 (47), A-58569 (44), and A-62066 (46), where modifications to the aromatic substitution enhanced potency, and A-58175 (42), where the amide linker was modified.

  DOI：

  10.1021/jm051185t

文献信息

• Benzodiazepine derivatives as app modulators
  申请人：——

  公开号：US20040082572A1

  公开（公告）日：2004-04-29

  A novel class of 1,4- and 1,5-benzodiazepines of formula (I) is disclosed. The compounds modulate the processing of amyloid precursor protein by &ggr;-secretase, and hence find use in the treatment or prevention of conditions associated with the deposition of &bgr;-amyloid, such as Alzheimer's disease. 1

  公开了一种式(I)的新型1,4-和1,5-苯二氮平类化合物。这些化合物调节&ggr;-分泌酶对淀粉样前体蛋白的加工作用，因此可用于治疗或预防与&bgr;-淀粉样蛋白沉积相关的疾病，如阿尔茨海默病。
• US7105509B2
  申请人：——

  公开号：US7105509B2

  公开（公告）日：2006-09-12
• 1,4-Benzodiazepines as Inhibitors of Respiratory Syncytial Virus
  作者：Malcolm C. Carter、Dagmar G. Alber、Robert C. Baxter、Sian K. Bithell、Jo Budworth、Ann Chubb、G. Stuart Cockerill、Verity C. L. Dowdell、Elisa A. Henderson、Sally J. Keegan、Richard D. Kelsey、Michael J. Lockyer、Jeremy N. Stables、Lara J. Wilson、Kenneth L. Powell

  DOI：10.1021/jm051185t

  日期：2006.4.1

  Respiratory syncytial virus (RSV) is the cause of one-fifth of all lower respiratory tract infections worldwide and is increasingly being recognized as a serious threat to patient groups with poorly functioning immune systems. Our approach to finding a novel inhibitor of this virus was to screen a 20 000-member diverse library in a whole cell XTT assay. Parallel assays were carried out in the absence of virus in order to quantify any associated cell toxicity. This identified 100 compounds with IC50's less than 50 mu M. A-33903 (18), a 1,4-benzodiazepine analogue, was chosen as the starting point for lead optimization. This molecule was moderately active and demonstrated good pharmacokinetic properties. The most potent compounds identified from this work were A-58568 (47), A-58569 (44), and A-62066 (46), where modifications to the aromatic substitution enhanced potency, and A-58175 (42), where the amide linker was modified.