3-Amino-5-benzo[1,3]dioxol-5-yl-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one | 376584-86-0

• 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-benzo[1,3]dioxol-5-yl-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one
• 英文别名: 3-amino-5-(1,3-benzodioxol-5-yl)-1-methyl-3H-1,4-benzodiazepin-2-one
• CAS: 376584-86-0
• 化学式: C₁₇H₁₅N₃O₃
• 分子量: 309.324
• InChiKey: AGHDZJDEBPBXIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(S)-methyl-3-(3,4-difluorophenyl)propionic acid 、 3-Amino-5-benzo[1,3]dioxol-5-yl-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以70%的产率得到(S)-N-((S)-5-Benzo[1,3]dioxol-5-yl-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-3-(3,4-difluoro-phenyl)-2-methyl-propionamide
  参考文献：
  名称：

  High affinity, bioavailable 3-Amino-1,4-benzodiazepine-Based γ-Secretase inhibitors

  摘要：

  In this paper, we describe the development of a novel series of high affinity, orally bioavailable 3-amino-1,4 benzodiazepine-based gamma-secretase inhibitors for the potential treatment of Alzheimer's disease. We disclose structure-activity relationships based around the 1, 3 and 5 positions of the benzodiazepine core structure. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.031
• 作为产物：
  描述：

  (5-Chloro-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester 在 四(三苯基膦)钯 、 sodium hydride 、 sodium carbonate 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Amino-5-benzo[1,3]dioxol-5-yl-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one
  参考文献：
  名称：

  High affinity, bioavailable 3-Amino-1,4-benzodiazepine-Based γ-Secretase inhibitors

  摘要：

  In this paper, we describe the development of a novel series of high affinity, orally bioavailable 3-amino-1,4 benzodiazepine-based gamma-secretase inhibitors for the potential treatment of Alzheimer's disease. We disclose structure-activity relationships based around the 1, 3 and 5 positions of the benzodiazepine core structure. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.031

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
• High affinity, bioavailable 3-Amino-1,4-benzodiazepine-Based γ-Secretase inhibitors
  作者：Andrew P. Owens、Alan Nadin、Adam C. Talbot、Earl E. Clarke、Timothy Harrison、Huw D. Lewis、Michael Reilly、Jonathan D.J. Wrigley、José L. Castro

  DOI：10.1016/j.bmcl.2003.07.031

  日期：2003.11

  In this paper, we describe the development of a novel series of high affinity, orally bioavailable 3-amino-1,4 benzodiazepine-based gamma-secretase inhibitors for the potential treatment of Alzheimer's disease. We disclose structure-activity relationships based around the 1, 3 and 5 positions of the benzodiazepine core structure. (C) 2003 Elsevier Ltd. All rights reserved.