methyl 3-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-5-nitrobenzoate | 706792-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-5-nitrobenzoate
• 英文别名: Methyl 3-(1,1-dioxothiazinan-2-yl)-5-nitrobenzoate
• CAS: 706792-92-9
• 化学式: C₁₂H₁₄N₂O₆S
• 分子量: 314.319
• InChiKey: WUVTVLWFHRCPTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-5-nitrobenzoate 在 10% Pd/C 、 甲酸铵 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以379 mg的产率得到methyl 3-amino-5-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)benzoate
  参考文献：
  名称：

  Second Generation of Hydroxyethylamine BACE-1 Inhibitors: Optimizing Potency and Oral Bioavailability

  摘要：

  BACE-1 inhibition has the potential to provide a disease-modifying therapy for the treatment of Alzheimer's disease. Optimization of a first generation of BACE-1 inhibitors led to the discovery of novel hydroxyethylamines (HEAs) bearing a tricyclic nonprime side. These derivatives have nanomolar cell potency and are orally bioavailable.

  DOI：

  10.1021/jm800138h
• 作为产物：
  描述：

  methyl 3-{bis[(4-chlorobutyl)sulfonyl]amino}-5-nitrobenzoate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以80%的产率得到methyl 3-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-5-nitrobenzoate
  参考文献：
  名称：

  Second Generation of Hydroxyethylamine BACE-1 Inhibitors: Optimizing Potency and Oral Bioavailability

  摘要：

  BACE-1 inhibition has the potential to provide a disease-modifying therapy for the treatment of Alzheimer's disease. Optimization of a first generation of BACE-1 inhibitors led to the discovery of novel hydroxyethylamines (HEAs) bearing a tricyclic nonprime side. These derivatives have nanomolar cell potency and are orally bioavailable.

  DOI：

  10.1021/jm800138h

文献信息

• [EN] HYDROXYETHYLAMINE DERIVATIVES FOR THE TREATMENT OF ALZHEIMER'S DISEASE<br/>[FR] DERIVES D'HYDROXYETHYLAMINE UTILISES POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：GLAXO GROUP LTD

  公开号：WO2004050619A1

  公开（公告）日：2004-06-17

  The present invention relates to novel hydroxyethylamine compounds of formula (I): (I) having Asp2 (-secretase, BACE1 or Memapsin) inhibitory activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases characterised by elevated - amyloid levels or -amyloid deposits, particularly Alzheimer's disease.

  本发明涉及具有Asp2（-分泌酶，BACE1或Memapsin）抑制活性的新型羟乙基胺化合物的化学式（I）：（I），其制备方法，含有它们的组合物以及它们在治疗由高β-淀粉样蛋白水平或β-淀粉样蛋白沉积所特征的疾病中的应用，特别是阿尔茨海默病。
• Hydroxyethylamine derivatives for the treatment of alzheimer's disease
  申请人：Demont H Emmanuel

  公开号：US20060025459A1

  公开（公告）日：2006-02-02

  The present invention relates to novel hydroxyethylamine compounds having Asp2 (β-secretase, BACE1 or Memapsin) inhibitory activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases characterised by elevated β-amyloid levels or β-amyloid deposits, particularly Alzheimer's disease.

  本发明涉及具有Asp2（β-秘鲁酶、BACE1或Memapsin）抑制活性的新型羟乙基胺化合物，其制备方法，包含它们的组合物以及它们在治疗由高β-淀粉样蛋白水平或β-淀粉样蛋白沉积物所特征的疾病，特别是阿尔茨海默病中的应用。
• HYDROXYETHYLAMINE DERIVATIVES FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：GLAXO GROUP LIMITED

  公开号：EP1567488B1

  公开（公告）日：2007-02-21
• US7253198B2
  申请人：——

  公开号：US7253198B2

  公开（公告）日：2007-08-07
• Second Generation of Hydroxyethylamine BACE-1 Inhibitors: Optimizing Potency and Oral Bioavailability
  作者：Nicolas Charrier、Brian Clarke、Leanne Cutler、Emmanuel Demont、Colin Dingwall、Rachel Dunsdon、Philip East、Julie Hawkins、Colin Howes、Ishrut Hussain、Phil Jeffrey、Graham Maile、Rosalie Matico、Julie Mosley、Alan Naylor、Alistair O’Brien、Sally Redshaw、Paul Rowland、Virginie Soleil、Kathrine J. Smith、Sharon Sweitzer、Pam Theobald、David Vesey、Daryl S. Walter、Gareth Wayne

  DOI：10.1021/jm800138h

  日期：2008.6.1

  BACE-1 inhibition has the potential to provide a disease-modifying therapy for the treatment of Alzheimer's disease. Optimization of a first generation of BACE-1 inhibitors led to the discovery of novel hydroxyethylamines (HEAs) bearing a tricyclic nonprime side. These derivatives have nanomolar cell potency and are orally bioavailable.