4-(3-amino-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide | 376584-00-8

• 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: 4-(3-amino-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide
• 英文别名: 4(3-amino-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide；4-(3-amino-1-methyl-2-oxo-3H-1,4-benzodiazepin-5-yl)benzamide
• CAS: 376584-00-8
• 化学式: C₁₇H₁₆N₄O₂
• 分子量: 308.34
• InChiKey: OFPYQNOWFFPCGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 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：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4-二氯苯基)丙酸 、 4-(3-amino-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (+/-)-4-[3-{[3-(3,4-dichlorophenyl)propanoyl]amino}-1-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-5-yl]benzamide
  参考文献：
  名称：

  A new series of potent benzodiazepine γ-secretase inhibitors

  摘要：

  A new series of benzodiazepine-containing gamma-secretase inhibitors with potential use in the treatment of Alzheimer's disease is disclosed. Structure-activity relationships of the pendant hydrocinnamate side-chain which led to the preparation of highly potent inhibitors are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00909-5
• 作为产物：
  描述：

  1-甲基-3,4-二氢-1H-苯并[e][1,4]二氮杂卓-2,5-二酮 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 potassium tert-butylate 、 氢溴酸 、 氢气 、 碘 、 sodium hydride 、 sodium carbonate 、 氯化铵 、 1-羟基苯并三唑 、 magnesium 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4-(3-amino-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzamide
  参考文献：
  名称：

  A new series of potent benzodiazepine γ-secretase inhibitors

  摘要：

  A new series of benzodiazepine-containing gamma-secretase inhibitors with potential use in the treatment of Alzheimer's disease is disclosed. Structure-activity relationships of the pendant hydrocinnamate side-chain which led to the preparation of highly potent inhibitors are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00909-5

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。
• Benzodiazepine derivatives as inhibitors of gamma secretase
  申请人：——

  公开号：US20040024203A1

  公开（公告）日：2004-02-05

  Compounds of formula (I) are disclosed. The compounds inhibit the action of gamma secretase, and hence find use in the treatment and prevention of Alzheimer's disease.

  公式（I）的化合物被披露。这些化合物抑制γ-分泌酶的作用，因此可用于治疗和预防阿尔茨海默病。
• [EN] BENZODIAZEPINE DERIVATIVES AS APP MODULATORS<br/>[FR] DERIVES DE BENZODIAZEPINE UTILISES COMME MODULATEURS DE LA PROTEINE PRECURSEUR AMYLOIDE (APP)
  申请人：MERCK SHARP & DOHME

  公开号：WO2001090084A1

  公开（公告）日：2001-11-29

  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 η-secretase, and hence find use in the treatment or prevention of conditions associated with the deposition of β-amyloid, such as Alzheimer's disease.

  一种新型的1,4-和1,5-苯二氮平类化合物的式(I)被揭示。这些化合物通过调节η-分泌酶对淀粉样前体蛋白的加工，因此可用于治疗或预防与β-淀粉样蛋白沉积有关的疾病，如阿尔茨海默病。
• Benzodiazepine derivatives as APP modulators
  申请人：Merck Sharp & Dohme Limited

  公开号：US07105509B2

  公开（公告）日：2006-09-12

  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 γ-secretase, and hence find use in the treatment or prevention of conditions associated with the deposition of β-amyloid, such as Alzheimer's disease

  揭示了一类新型的1,4-和1,5-苯二氮平类化合物(I)。这些化合物通过调节γ-分泌酶对淀粉样前体蛋白的处理，因此可用于治疗或预防与β-淀粉样蛋白沉积相关的疾病，如阿尔茨海默病。
• 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.